[ CAS No. 6674-22-2 ] {[proInfo.proName]}

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Quality Control of [ 6674-22-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 6674-22-2 ]

Product Citations Expand+

Structure-Based Drug Design of ADRA2A Antagonists Derived from Yohimbine

Artem Chayka ; Michal ?esnek ; Erika Ku?mová , et al. JMC,2024,67(12):10135-10151. DOI: 10.1021/acs.jmedchem.4c00323 PubMed ID: 38857067

Abstract: Yohimbine, a natural indole alkaloid and a nonselective adrenoceptor antagonist, possesses potential benefits in treating inflammatory disorders and sepsis. Nevertheless, its broader clinical use faces challenges due to its low receptor selectivity. A structure–activity relationship study of novel yohimbine analogues identified amino esters of yohimbic acid as potent and selective ADRA2A antagonists. Specifically, amino ester 4n, in comparison to yohimbine, showed a 6-fold higher ADRA1A/ADRA2A selectivity index (SI > 556 for 4n) and a 25-fold higher ADRA2B/ADRA2A selectivity index. Compound 4n also demonstrated high plasma and microsomal stability, moderate-to-low membrane permeability determining its limited ability to cross the blood–brain barrier, and negligible toxicity on nontumor normal human dermal fibroblasts. Compound 4n represents an important complementary pharmacological tool to study the involvement of adrenoceptor subtypes in pathophysiologic conditions such as inflammation and sepsis and a novel candidate for further preclinical development to treat ADRA2A-mediated pathologies.

Purchased from AmBeed: 25952-53-8 ; 36805-97-7 ; 6674-22-2

Are β-Lactones Involved in Carbon-Based Olefination Reactions?

Jan Nowak ; Micha? Tryniszewski ; Micha? Barbasiewicz Synlett,2024,35(10):1190-1194. DOI: 10.1055/a-2268-4386

Abstract: Heteroatom-based olefinating reagents (e.g., organic phosphonates, sulfonates, etc.) are used to transform carbonyl compounds into alkenes, and their mechanism of action involves aldol-type addition, cyclization, and fragmentation of four-membered ring intermediates. We have developed an analogous process using ethyl 1,1,1,3,3,3-hexafluoroisopropyl methylmalonate, which converts electrophilic aryl aldehydes into α-methylcinnamates in up to 70% yield. The reaction plausibly proceeds through the formation of β-lactone that spontaneously decarboxylates under the reaction conditions. The results shed light on the Knoevenagel–Doebner olefination, for which decarboxylative anti-fragmentation of aldol-type adducts is usually considered.

Keywords: olefination ; carbonyl compounds ; reaction mechanism ; lactones ; malonates ; Knoevenagel ; Doebner reaction

Purchased from AmBeed: 587-04-2 ; 609-08-5 ; 29166-72-1 ; 99-61-6 ; 555-16-8 ; 104-88-1 ; 6674-22-2

INVESTIGATIONS OF S (IV) FLUORIDES AND THEIR UTILITY IN SMALL MOLECULE SYNTHESES

Thomson, Brodie ; University of St Andrews,2024.

Abstract: Sulfur(IV) fluorides are powerful synthetic reagents typically used in the fluorination of small molecules. Traditional examples, including SF₄ and DAST, were primarily applied in the deoxyfluorinations of alcohols, carbonyls and carboxylic acids. More recent sulfur(IV) fluoride analogues, including thionyl fluoride and XtalFluor-E? , display unique reactivity relative to DAST and SF₄, yet have rarely been applied outside of similar organic transformations. In this thesis, the unique reactivities of thionyl fluoride and XtalFluor-E? were investigated and utilised towards the synthesis of acyl fluorides, sulfonyl fluorides, sulfinyl fluorides, and arylaminooxetanes. Chapter 2 describes the utilization of thionyl fluoride in a carboxylic acid activation strategy to synthesize acyl fluorides. The desired products were synthesized in high yields (60–99%) under mild conditions and quantified either in solution using ¹⁹F NMR spectroscopy or isolated in a column-free protocol. Chapter 3 describes the efforts made in improving the synthesis of sulfonyl fluorides and sulfinyl fluorides. In one transformation, sulfonic acids were derivatized in a DMF-promoted, thionyl fluoride-mediated fluorination, affording sulfonyl fluorides in high yields (80-99%). A complementary strategy utilising XtalFluor-E? accessed the same products in good isolated yields (41-94%), but milder conditions. Thionyl fluoride was also used to transform sulfinic acids to sulfinyl fluorides in a one-pot strategy, accessing sulfinyl fluorides in high crude yields (75-98%) quantified by ¹⁹F NMR spectroscopy. This represents the first general method reported towards their synthesis. Chapter 4 describes an expedited route towards the synthesis of arylamino-oxetanes via the XtalFluor-E?-mediated activation of 3-aryloxetan-3-ols. The optimised protocol accessed arylamino-oxetanes under mild conditions and reduced the number of steps required in their syntheses (between 2-6) compared to current literature procedures. This represents the shortest and simplest route towards their synthesis, accessing the desired products in 34-97% isolated yields. Chapter 6 is a distinct chapter in collaboration with Delic Laboratories, UBC and BAT, in which the light-induced degradation of CBD solutions was investigated. CBD-hydroxyquinone was identified to undergo a light-induced photo-isomerisation to form a previously unidentified cannabinoid intermediate. Both experimental and computation studies identified this intermediate reacts rapidly with oxygen to form a multitude of products in solution.

Purchased from AmBeed: 1112-67-0 ; 1643-19-2 ; 1122-58-3 ; 6674-22-2

Product Details of [ 6674-22-2 ]

CAS No. :	6674-22-2	MDL No. :	MFCD00006930
Formula :	C₉H₁₆N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GQHTUMJGOHRCHB-UHFFFAOYSA-N
M.W :	152.24	Pubchem ID :	81184
Synonyms :

Calculated chemistry of [ 6674-22-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.89
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.97
TPSA :	15.6 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.14
Log Po/w (XLOGP3) :	1.38
Log Po/w (WLOGP) :	0.9
Log Po/w (MLOGP) :	1.88
Log Po/w (SILICOS-IT) :	2.41
Consensus Log Po/w :	1.74

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.65
Solubility :	3.38 mg/ml ; 0.0222 mol/l
Class :	Very soluble
Log S (Ali) :	-1.31
Solubility :	7.44 mg/ml ; 0.0489 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.73
Solubility :	2.84 mg/ml ; 0.0187 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.95

Safety of [ 6674-22-2 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P234-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338	UN#:	2922
Hazard Statements:	H290-H301-H314-H412	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 6674-22-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 6674-22-2 ]
Downstream synthetic route of [ 6674-22-2 ]

[ 6674-22-2 ] Synthesis Path-Upstream 1~1

1
[ 13734-36-6 ]
[ 6674-22-2 ]
[ 74-88-4 ]
[ 42492-57-9 ]

Reference： [1] Patent: US5494925, 1996, A,
[2] Patent: US5512576, 1996, A,
[3] Patent: US5541168, 1996, A,
[4] Patent: US5556909, 1996, A,
[5] Patent: US5602154, 1997, A,

[ 6674-22-2 ] Synthesis Path-Downstream 1~19

1
[ 6674-22-2 ]
(E)-ethyl-3-(4-amino-2-(methylthio)pyrimidin-5-yl)acrylic acid [ No CAS ]
[ 211244-81-4 ]

Yield	Reaction Conditions	Operation in experiment
134 mg (45%)	In N-ethyl-N,N-diisopropylamine;	EXAMPLE 5 2-Methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one To a room temperature solution of ethyl 3-(4-amino-2-methanesulfanyl pyrimidin-5-yl)acrylate (368 mg, 1.53 mmol) in 3 mL of N,N-diisopropylethylamine is added 380 muL of 1,8-diazabicyclo[5,4,0]undec-7-ene. The reaction mixture is heated at reflux for 3 hours then cooled to room temperature and concentrated. The residue is purified by flash chromatography eluding with ethyl acetate. The fractions containing the product are partially concentrated in vacuo, and the solids are removed by filtration to provide 134 mg (45%) of 2-methanesulfanyl-8H-pyrido[-2,3-d]pyrimidin-7-one. mp 269-27 C. Analysis calculated for C8H7N3OS: C, 49.73: H, 3.65: N, 21.75. Found: C, 49.67: H, 3.46: N, 21.49.
134 mg (45%)	In N-ethyl-N,N-diisopropylamine;	Example 20 2-Methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one To a room temperature solution of ethyl 3-(4-amino-2-methanesulfanyl pyrimidin-5-yl)acrylate (368 mg, 1.53 mmol) in 3 mL of N,N-diisopropylethylamine was added 380 muL of 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction mixture was heated at reflux for 3 hours then cooled to room temperature and concentrated. The residue was purified by flash chromatography eluding with ethyl acetate. The fractions containing the product were partially concentrated in vacuo, and the solids were removed by filtration to provide 134 mg (45%) of 2-methanesulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one, mp 269-271 C. Analysis calculated for C8H7N3OS: C, 49.73; H, 3.65; N, 21.75. Found: C, 49.67; H, 3.46; N, 21.49.

Reference： [1]Patent: US2003/73668,2003,A1
[2]Patent: US2004/224958,2004,A1

2
(7R,9aS)-trans-2-(5-fluoro-benzo[d]isoxazol-3-yl)-7-(3-pyrrolidin-1-ylmethyl-phenoxymethyl)-octahydro-pyrido[1,2-a]pyrazine [ No CAS ]
[ 178747-50-7 ]
[ 144-55-8 ]
[ 6674-22-2 ]
(7R,9AS)-trans-2-(5-Fluoro-benzo[d]isoxazol-3-yl)-7-(3-pyrrolidin-1-ylmethyl-phenoxymethyl)-octahydropyrido[1,2-a]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In pyridine; diethyl ether; dichloromethane; ethyl acetate;	The Step 4 title compound (dihydrochloride salt; 125 mg, 0.31 mmol), 1,8-diazabicyclo[5.4.0]-undec-7-ene (153 mul, 1.0 mmol), and <strong>[178747-50-7]3-chloro-5-fluoro-benzo[d]isoxazole</strong> (66 mg, 0.39 mmol) were dissolved in pyridine (150 mul). The reaction was heated at 90 C. for 18 hours. 10% aqueous sodium bicarbonate and methylene chloride (15 ml of each) were added to the well-stirred mixture. The aqueous phase was then re-extracted with three 15 ml portions of fresh methylene chloride. The combined organic extracts were dried (anhydrous sodium sulfate) and the solvent was removed in vacuo. Purification of the oily semi-solid residue (150 mg) by flash chromatography (silica gel, 47-61 micron mesh; elution with methanol/methylene chloride=7.5:92.5 in volume) afforded the tile compound (free base) as a colorless amorphous solid (57 mg. 36% yield). Dissolution of the entire sample in ethyl acetate/methylene chloride (1.0 ml of each), addition of a saturated diethyl ether solution of anhydrous hydrogen chloride (3 ml); and finally, solvent removal in vacuo afforded the title compound dihydrochloride as an amorphous solid. Free base data: 13C NMR (75 MHz, CDCl3) delta161.62, 160.91, 159.45, 158.45, 141.54, 129.55, 121.70, 118.44, 116.88, 115.28, 113.35, 111.73, 107.76, 71.26, 61.21, 60.55, 59.20, 54.68, 54.60, 54.12, 48.71, 36.88, 29.43, 27.37, 23.90 ppm; MS m/z 465 (M+1).

Reference： [1]Patent: US6525048,2003,B1

3
4-methyl-5-methylthio-2-phenoxythiocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one [ No CAS ]
[ 1869-24-5 ]
[ 6674-22-2 ]
4-methyl-5-methylthio-2-(2-trifluoromethyl-phenylsulphonyl-aminothiocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; water; acetonitrile;	STR30 (by process (b)) At 20 C., 28.1 g (0.125 mol) of <strong>[1869-24-5]2-trifluoromethyl-benzenesulphonamide</strong> and a solution of 19 g of 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) in 50 ml of acetonitrile are added in succession to a solution of 28.1 g (0.10 mol) of 4-methyl-5-methylthio-2-phenoxythiocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 300 ml of acetonitrile. The reaction mixture is stirred at 20 C. until a clear solution is obtained. The solution is then concentrated under water pump vacuum and the residue is admixed with water and methylene chloride (300 ml each) and acidified with 2N hydrochloric acid. The organic phase is separated off, the aqueous phase is extracted once more with 100 ml of methylene chloride and the combined organic phases are dried with magnesium sulphate and filtered. The filtrate is concentrated under a water pump vacuum and the residue is crystallized from isopropanol. 29.6 g (72% of theory) of 4-methyl-5-methylthio-2-(2-trifluoromethyl-phenylsulphonyl-aminothiocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 154 C. are obtained. By the methods of Examples 1, 2 and 3 and in accordance with the general description of the preparation processes according to the invention, it is also possible to prepare, for example, the compounds of the formula (I) listed in Table 1 below. STR31

Reference： [1]Patent: US5972844,1999,A

4
[ 66655-67-2 ]
[ 155967-29-6 ]
[ 6674-22-2 ]
[ 134186-64-4 ]
[ 155967-82-1 ]

Yield	Reaction Conditions	Operation in experiment
10.4%	In N-methyl-acetamide; water;	i) Synthesis of 1,3-bis[3-(4-pyridylthio)propyl]-quinazoline-2,4(1H,3H)-dione To a solution of 1.62 g (10 mmol) of benzoylene urea and 1.88 g (10 mmol) of 4-(3-chloropropylthio)pyridine in 50 ml of dimethylformamide, 1.65 ml (11 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at 80 C. for 16 hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate/ethanol =25:1 to 10:1 to 2:1). First, 0.973 g of 3-[3-(4-pyridylthio)propyl]quinazoline-2,4-(1H,3H)-dione (31.1% yield, pale yellow crystals) was obtained, and then, 0.487 g of the desired product was obtained (10.4% yield, yellow oil). NMR (200 MHz, CDCl3) delta: 2.04-2.24 (4H, m), 3.02-3.16 (4H, m), 4.27-4.35 (4H, m), 7.08-7.30 (6H, m), 7.62 (1H, ddd, J=1.8, 7.0, 7.2 Hz), 8.23 (1H, dd, J=1.6, 8.0 Hz), 8.35-8 41 (4H, m).

Reference： [1]Patent: US5246948,1993,A

5
[1α,5α,6β]-6-amino-1-methyl-3-azabicyclo[3.2.0]heptane [ No CAS ]
[ 93107-30-3 ]
[ 6674-22-2 ]
7-([1α,5α,6β]-6-Amino-1-methyl-3-azabicyclo[3.2.0]heptane-3-yl)1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid,hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With hydrogenchloride; In acetonitrile;	EXAMPLE 1 7-([1alpha,5alpha,6beta]-6-Amino-1-methyl-3-azabicyclo[3.2.0]heptane-3-yl)1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid,hydrochloride To a suspension of 150 mg of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid in 5 ml of acetonitrile were added 200 mg of 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) and 200 mg of [1alpha,5alpha,6beta]-6-amino-1-methyl-3-azabicyclo[3.2.0]heptane. The reaction mixture was heated under reflux for an hour. The solvent was evaporated out under reduced pressure. To the residue was added 5 ml of an aqueous 5percent hydrochloric acid solution. The resulting mixture was stirred at room temperature for 3 hours. The solids were collected by filtration, washed with water and then ethanol, and dried to give 140 mg of the titled compound as pale-yellow solids (yield: 61percent). m.p.: 285°-290° C. 1 H-NMR(DMSO-d6 +TFA-d) delta: 8.55(1H, s), 8.00(1H, d, J=17 Hz), 7.24(1H, d, J=7.4 Hz), 4.3-3.5 (4H, m), 3.5-3.3(1H, m), 3.0-2.6(2H, m), 2.3-2.0(2H, m), 1.31(3H, s), 1.4-1.0(4H, m).

Reference： [1]Patent: US5527910,1996,A

6
[ 33543-78-1 ]
[ 54714-53-3 ]
[ 6674-22-2 ]
[ 156484-54-7 ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform; water;	a solution of 3.65 g of 1,8-diazabicyclo[5.4.0]undec-7-ene in 10 ml of chloroform is added dropwise over 20 minutes at a temperature close to 20° C. to a solution of 2.8 g of <strong>[33543-78-1]ethyl imidazole-2-carboxylate</strong> and 6.1 g of 2-bromo-5-chloro-1-indanone. After stirring for 2 hours and adding 100 ml of distilled water, the mixture is extracted 3 times with a total of 75 ml of chloroform and the organic extracts are pooled, dried over anhydrous magnesium sulphate and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 50° C. After silica gel chromatography with a dichloromethane-ethyl acetate mixture (70-30 by volume), 1 g of ethyl 1-(5-chloro-1-oxo-2-indanyl)imidazole-2-carboxylate is obtained in the form of a thick yellow oil Rf=0.3, thin-layer chromatography on silica gel; solvent: dichloromethane-ethyl acetate (70-30 by[volume)]. The 2-bromo-5-chloro-1-indanone can be prepared as described in German Patent 2,640,358.

Reference： [1]Patent: US5677306,1997,A

7
[ 93107-30-3 ]
[ 122433-74-3 ]
[ 6674-22-2 ]
[ 122433-65-2 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine;	EXAMPLE 7 1-Cyclopropyl-7-(6,8-diazabicyclo[3.2.2]non-6-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid A solution of 0.53 g (2.0 mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.44 g (2.2 mmol) of 6,8-diazabicyclo[3.2.2]nonane, dihydrochloride, 0.90 ml (6.0 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 10 ml of pyridine was heated under reflux for 4 hr. The reaction mixture was cooled to room temperature and the solid was filtered and washed with ethanol to yield 0.39 g of the title compound, mp 273°-276° dec.

Reference： [1]Patent: US4923879,1990,A

8
conc-hydrochloric acid [ No CAS ]
[ 93107-30-3 ]
[ 6674-22-2 ]
1,2,3,4,5,6-hexahydropyrrolo<3,4-c>pyrrole dihydrobromide [ No CAS ]
1-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0] oct-1⁽⁵⁾-en-3-yl]-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In methanol; acetonitrile;	EXAMPLE 18 1-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0] oct-1(5)-en-3-yl]-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride (KR-10787) <strong>[93107-30-3]1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid</strong> (1.07 g), 3,7-diazabicyclo[3.3.0] oct-1(5)-ene dihydrobromide (1.08 g) and 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU, 2 ml) were suspended in acetonitrile (20 ml) and refluxed for 3 hours. After cooling the reaction mixture, the produced precipitate was collected by filtration and washed with acetonitrile and methanol. The solid was dissolved in methanol (5 ml) and conc-hydrochloric acid (5 ml) and then insoluble portion was filtered off. The filtrate was concentrated under vacuum, washed with ethanol to give the title compound (0.95 g, yield 60percent) mp: 260°-263° C. 1 H-NMR(CDCl3 +CD3 COOD, delta ppm): 9.36 (1H, s), 7.87 (1H, d, J =12.2 Hz), 6.85 (1H, d, J=7.4 Hz), 4.50 (4H, s), 4.27 (4H, s), 3.53 (1H, m), 1.40 (2H, m), 1.27 (2H, m).
60%	In methanol; acetonitrile;	Example 18 1-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride (KR-10787) <strong>[93107-30-3]1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid</strong> (1.07 g), 3,7-diazabicyclo[3.3.0]oct-1(5)-ene dihydrobromide (1.08 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 2 ml) were suspended in acetonitrile (20 ml) and refluxed for 3 hours. After cooling the reaction mixture, the produced precipitate was collected by filtration and washed with acetonitrile and methanol. The solid was dissolved in methanol (5 ml) and conc-hydrochloric acid (5 ml) and then insoluble portion was filtered off. The filtrate was concentrated under vacuum, washed with ethanol to give the title compound (0.95 g, yield 60percent) mp: 260 - 263°C 1H-NMR (CDCl3 + CD3COOD, delta ppm): 9.36 (1H, s), 7.87 (1H, d, J = 12.2 Hz), 6.85 (1H, d, J = 7.4 Hz), 4.50 (4H, s), 4.27 (4H, s), 3.53 (1H, m), 1.40 (2H, m), 1.27 (2H, m)

Reference： [1]Patent: US5091384,1992,A
[2]Patent: EP424850,1991,A1

9
8-methyl-3,8-diazabicyclo(3.2.1)octane dihydrochloride [ No CAS ]
[ 93107-30-3 ]
[ 6674-22-2 ]
[ 108461-05-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	In pyridine; chloroform;	EXAMPLE 27 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-(8-methyl-3,8-diazabicyclo[3.2.1]oct-3-yl)-4-oxo-3-quinoline carboxylic acid (R1 =H; Y=cyclopropyl; A=CH; R2 =a; m=1; n=2; Q=methyl) A stirred suspension of 6,7-difluoro-1-cyclopropyl-4-oxo-1,4-dihydro-3-quinoline carboxylic acid (1.5 g, 5.66 mmol) and 8-methyl-3,8-diazabicyclo-[3.2.1]octane dihydrochloride (1.45 g, 7.32 mmol) in 10.0 ml of pyridine was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (2.26 g, 14.9 mmol). The reaction mixture was heated to 80° C. for 4 hours, cooled to room temperature and poured into 250 ml of chloroform. The chloroform layer was washed with water (twice 200 ml), dried over sodium sulfate, filtered and concentrated in vacuo. The crude off white solid was dissolved in 1N hydrochloride with warming and this solution was washed with chloroform/methanol (9:1 v/v). The aqueous solution as then basified with saturated aqueous sodium bicarbonate and extracted with chloroform (three times 200 ml). The chloroform layer was dried with sodium sulfate, filtered, concentrated in vacuo, and washed with diethyl ether to give 1.80 g (86percent yield) of an off white solid, m.p. 278°-279° C. with decomposition.
86%	In pyridine; chloroform;	EXAMPLE 27 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-(8-methyl-3,8-diazabicyclo[3.2.1]oct-3-yl)-4-oxo-3-quinoline carboxylic acid (R1 =H; Y=cyclopropyl; A=CH; R2 =a; m=1; n=2; Q=methyl) A stirred suspension of 6,7-difluoro-1-cyclopropyl-4-oxo-1,4-dihydro-3-quinoline carboxylic acid (1.5 g, 5.66 mmol) and 8-methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride (1.45 g, 7.32 mmol) in 10.0 ml of pyridine was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (2.26 g, 14.9 mmol). The reaction mixture was heated to 80° C. for 4 hours, cooled to room temperature and poured into 250 ml of chloroform. The chloroform layer was washed with water (twice 200 ml), dried over sodium sulfate, filtered and concentrated in vacuo. The crude off white solid was dissolved in 1N hydrochloride with warming and this solution was washed with chloroform/methanol (9:1 v/v). The aqueous solution as then basified with saturated aqueous sodium bicarbonate and extracted with chloroform (three times 200 ml). The chloroform layer was dried with sodium sulfate, filtered, concentrated in vacuo, and washed with diethyl ether to give 1.80 g (86percent yield) of an off white solid, m.p. 278°-279° C. with decomposition.

Reference： [1]Patent: US5091383,1992,A
[2]Patent: US4861779,1989,A

10
1-amino-5-azaspiro[2.4]heptane hydrochloride [ No CAS ]
[ 93107-30-3 ]
[ 6674-22-2 ]
7-(1-amino-5-azaspiro[2.4]heptane-5-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.8%	In acetonitrile;	Example 5 Preparation of 7-(1-amino-5-azaspiro[2,4]heptane-5-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 0.31g(1.17mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 0.26g(1.40mmol) of 1-amino-5-azaspiro[2,4]heptane hydrochloride and 0. 53g(3.48mmol) of 1,8-diazabicyclo[5,4,0]undec-7-ene were dissolved in 5m of acetonitrile; and the resulting solution was refluxed for 3 hours and cooled to room temperature. The solid produced was filtered, washed with chilled acetonitrile, water and ethylether in turn and dried under a reduced pressure to obtain 0.30g of the desired compound(yield: 71.8percent). m.p.: 222~224°C

Reference： [1]Patent: EP550016,1993,A1

11
1-methylamino-5-azaspiro[2.4]heptane hydrochloride [ No CAS ]
[ 93107-30-3 ]
[ 6674-22-2 ]
1-cyclopropyl-6-fluoro-7-(1-methylamino-5-azaspiro[2.4] heptane-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	In acetonitrile;	Example 11 Preparation of 7-(1-methylamino-5-azaspiro[2,4]heptane-5-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 0.19g(0.72mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 0.17g(0.86mmol) of 1-methylamino-5-azaspiro[2,4]heptane hydrochloride and 0.37g(2.43mmol) of 1,8-diazabicyclo[5,4,0]undec-7-ene were dissolved in 3m of acetonitrile; and the resulting solution was refluxed for 3 hours and cooled to room temperature. The solid produced was filtered, washed with chilled acetonitrile, water and ethylether in turn and dried under a reduced pressure to obtain 0.15g of the desired compound(yield: 56percent). m.p.: 230~233°C

Reference： [1]Patent: EP550016,1993,A1

12
[ 1111-97-3 ]
[ 38183-03-8 ]
[ 6674-22-2 ]
[ 786706-00-1 ]

Yield	Reaction Conditions	Operation in experiment
69%	With CuCl2; In acetonitrile;	Example 29 7,8-Bis-(1,1-dimethyl-prop-2-ynyloxy)-2-phenyl-chromen-4-one To a suspension of 7,8-dihydroxy-2-phenyl-chromen-4-one (510 mg, 2 mmol) and CuCl2 (16 mg, 0.12 mmol) in acetonitrile (3 mL) was added 3-chloro-3-methyl-1-butyne (0.5 mL, 4.56 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.78 mL, 5.2 mmol) slowly at 0 C. The dark mixture was stirred at 0 C. for 5 h and then at room temperature overnight. The solvent was evaporated and the residue was purified by column chromatography (SiO2, EtOAc:hexanes/10-50%) to give the title compound as a white solid (540 mg, 69%): 1H NMR (CDCl3, 300 MHz) delta 8.02 (m, 2H), 7.96 (d, J=9.0 Hz, 1H), 7.69 (d, J=9.0 Hz, 1H), 7.53 (m, 3H), 6.78 (s, 1H), 2.66 (s, 1H), 2.26 (s, 1H), 1.81 (s, 6H), 1.76 (s, 6H).

Reference： [1]Patent: US2005/4026,2005,A1

13
[ 81131-70-6 ]
[ 6674-22-2 ]
[ 1159685-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ethyl acetate; at 50℃; for 1h;Product distribution / selectivity;	a) A solution of DBU (0.844 ml, 5.6 mmol) in ethyl acetate (10 ml) was added dropwise to 40 ml of solution 1 (5.6 mmol pravastatin) prepared as in Example 11 at 5O0C after which pravastatin DBU salt precipitated as an oil. b) Experiment a) was repeated however 40 ml of solution 1 was diluted with ethanol (2 ml); again pravastatin DBU salt precipitated as an oil. c) Experiment a) was repeated however 40 ml of solution 1 was diluted with ethanol (4 ml); again pravastatin DBU salt precipitated as an oil. d) Solution 1 (40 ml, 5.6 mmol pravastatin was added dropwise in 1 h at 5O0C to a solution of 1 ,8-diazabicyclo[5.4.0]undec-7-ene (0.844 ml, 5.6 mmol) in ethyl acetate (10 ml) after which pravastatin DBU salt precipitated as an oil.
	In ethanol;Product distribution / selectivity;	a) A solution of DBU (0.844 ml, 5.6 mmol) in ethyl acetate (10 ml) was added dropwise to 40 ml of solution 1 (5.6 mmol pravastatin) prepared as in Example 11 at 5O0C after which pravastatin DBU salt precipitated as an oil. b) Experiment a) was repeated however 40 ml of solution 1 was diluted with ethanol (2 ml); again pravastatin DBU salt precipitated as an oil. c) Experiment a) was repeated however 40 ml of solution 1 was diluted with ethanol (4 ml); again pravastatin DBU salt precipitated as an oil. d) Solution 1 (40 ml, 5.6 mmol pravastatin was added dropwise in 1 h at 5O0C to a solution of 1 ,8-diazabicyclo[5.4.0]undec-7-ene (0.844 ml, 5.6 mmol) in ethyl acetate (10 ml) after which pravastatin DBU salt precipitated as an oil.

Reference： [1]Patent: WO2009/68556,2009,A1 .Location in patent: Page/Page column 12
[2]Patent: WO2009/68556,2009,A1 .Location in patent: Page/Page column 12

14
[ 524-38-9 ]
[ 3386-35-4 ]
[ 6674-22-2 ]
[ 65764-49-0 ]

Yield	Reaction Conditions	Operation in experiment
9.40 g (98%)	With sodium hydrogencarbonate; In ethyl acetate; N,N-dimethyl-formamide;	a) Synthesis of 2-(octyloxy)-1H-isoindole-1,3(2H)-dione A solution of 2-hydroxy-1,3-isoindoledione (5.76 g, 35.2 mmol), octyl 4-methylbenzenesulfonate (10.00 g, 35.2 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 5.35 g, 35.2 mmol) in DMF (300 ml) was heated at 80 C. for 17 h. The color of the reaction mixture turned from dark brown to clear yellow. The reaction mixture was concentrated, taken up in ethyl acetate, washed with a saturated solution of NaHCO3 (3*) until the organic phase became colorless. Drying (Na2SO4) and concentrating gave 9.40 g (98%) of a yellow oil that slowly crystallizes. 1H-NMR (CDCl3): 7.88-7.81 (m, 2H); 7.79-7.71 (m, 2H); 4.20 (t, J=6.9, 2H); 1.85-1.74 (m, 2H); 1.54-1.42 (m, 2H); 1.41-1.20 (m, 8H); 0.88 (t, J=6.9, 3H). 13C-NMR (CDCl3): 163.69 (s); 134.42 (d); 129.02 (s); 123.48 (d); 78.66 (t); 31.78 (t); 29.29 (t); 29.16 (t); 28.17 (t); 25.56 (t); 22.65 (t); 14.09 (q).

Reference： [1]Patent: US2010/226875,2010,A1

15
[ 6674-22-2 ]
[ 4016-63-1 ]
C₉H₁₆N₂*2C₁₀H₁₂BrN₅O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	In methanol;	To a solution of <strong>[4016-63-1]8-bromoguanosine</strong> (50 mg, 0.138 mmol) in methanol (10 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (10.6 muL, 0.069 mmol, 97percent) was added. After 6 days and selection of single crystals suitable for X-ray diffraction experiments, the remaining crystals were filtered off and dried in vacuum yielding 38 mg (62percent) of the adduct [8-BrG][8-BrG]-[DBU-H]+: IR (KBr) lambdamax/cm-1: 3467, 3331, 3304, 3194, 3130, 2981, 2946, 2929, 2916, 2859, 1697, 1675, 1650, 1621, 1589, 1571, 1525, 1468, 1406, 1322, 1314, 1121, 1082, 1074, 1049. The integrals of protons are expressed in the ratio 1:0.5; for 2 equiv of nucleoside and 1 equiv of DBU. 1H NMR (DMSO-d6) delta/ppm: 6.80 (br s, 2H, NH2), 6.60-4.8 (br s, 3H, OH-2', OH-3', OH-5'), 5.68 (d, 1H, J=6.8 Hz, H-1'), 5.02 (t, 1H, J=6.0 Hz, H-2'), 4.13 (m, 1H, H-3'), 3.91 (m, 1H, H-4'), 3.67 (dd, 1H, J=3.6, 12.1 Hz, H-5'a), 3.50-3.55 (m, 2H, H-5'b, CH2-6), 3.44 (t, 1H, J=5.7 Hz, CH2-2), 3.24 (t, 1H, J=5.7 Hz, CH2-4), 2.62 (m, 1H, CH2-10), 1.89 (m, 1H, CH2-3), 1.62 (m, 3H, CH2-7, CH2-8, CH2-9) (see Supplementary data for details, Fig. S1); 13C NMR (DMSO-d6) delta/ppm: 164.91 (s, C-5a), 161.25 (s, C-6), 157.15 (s, C-2), 151.98 (s, C-4), 119.65 (s, C-8), 118.03 (s, C-5), 89.82 (d, C-1'), 86.35 (d, C-4'), 70.96 (d, C-3'), 70.59 (d, C-2'), 62.30 (t, C-5'), 53.20 (t, C-6), 47.81 (t, C-2), 38.09 (t, C-4), 32.01 (t, C-10), 28.25 (t, C-7), 26.06 (t, C-9), 23.50 (t, C-8), 19.14 (t, C-3) (see Supplementary data for details, Fig. S2). The assignments of the protons and C-atoms were confirmed by 2D NMR spectra; see Supplementary data for details: COSY spectrum (Fig. S3), NOESY spectrum (Fig. S4) and 1H-13C HMQC spectrum (Fig. S5). Anal. Calcd for C29H40Br2N12O10 (Mr=876.51): C, 39.74; H, 4.60; N, 19.18. Found: C, 39.85; H, 4.50; N, 19.26.

Reference： [1]Tetrahedron,2012,vol. 68,p. 1062 - 1070

16
[ 6674-22-2 ]
[ 4016-63-1 ]
[ 1357158-20-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	In methanol; at 20℃; for 1h;	To a suspension of <strong>[4016-63-1]8-bromoguanosine</strong> (200 mg, 0.552 mmol) in dry methanol (10 mL), DBU (85 muL, 0.552 mmol, 97percent) was added dropwise. The resulting solution was stirred at room temperature for 1 h, evaporated to half of its volume and left in the fridge for 16 h. The resulting solid precipitate was filtered off, washed with ether and dried in a vacuum desiccator over solid NaOH, yielding 250 mg (88percent) of salt [8-BrG]-[DBU-H]+: IR (KBr) lambdamax/cm-1: 3466, 3424, 3336, 3202, 2924, 1653, 1616, 1580, 1560, 1458, 1437, 1306, 1275, 1128, 1084, 1065, 1005; 1H NMR (DMSO-d6) delta/ppm: 6.31 (br s, 2H, NH2), 5.67 (d, 1H, J=6.9 Hz, H-1'), 5.00 (t, 1H, J=6.0 Hz, H-2'), 4.12-3.2(br s, 3H, OH-2', OH-3', OH-5'), 4.12 (m, 1H, H-3'), 3.92 (m, 1H, H-4'), 3.66 (dd, 1H, J=3.3, 12.2 Hz, H-5'a), 3.52 (dd, 2H, J=3.6, 12.2 Hz, H-5'b), 3.40 (m, 2H, CH2-6), 3.36 (t, 2H, J=5.7 Hz, CH2-2), 3.19 (pt, 2H, J=5.7 Hz, CH2-4), 2.53 (m, 2H, CH2-10), 1.82 (m, 2H, CH2-3), 1.59 (m, 6H, CH2-7, CH2-8, CH2-9) (see Supplementary data for details Fig. S7); 13C NMR (DMSO-d6) delta/ppm: 163.44 (s, C-5a), 162.10 (s, C-6), 157.73 (s, C-2), 151.71 (s, C-4), 119.12 (s, C-8), 118.49 (s, C-5), 89.95 (d, C-1'), 86.51 (d, C-4'), 71.10 (d, C-2'(C-3')), 70.67 (d, C-3' (C-2')), 62.39 (t, C-5'), 52.80 (t, C-6), 47.72 (t, C-2), 39.59 (t, C-4), 33.20 (t, C-10), 28.48 (t, C-7), 26.64 (t, C-9), 24.15 (t, C-8), 20.04 (t, C-3) (see Supplementary data for details, Fig. S8). Anal. Calcd for C19H28BrN7O5 (Mr=514.38): C, 44.37; H, 5.49; N, 19.06. Found: C, 44.50; H, 5.31; N, 19.22.

Reference： [1]Tetrahedron,2012,vol. 68,p. 1062 - 1070

17
[ 1409950-08-8 ]
[ 6674-22-2 ]
[ 530-62-1 ]
[ 159622-10-3 ]
[ 1409964-03-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogenchloride; In N,N-dimethyl-formamide;	Step 4 To a solution of <strong>[159622-10-3](1R,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid</strong> (7.5 g, 33 mmol) in DMF (50 mL) was added 1,1'-carbonyldiimidazole ("CDI", 10.7 g, 66.0 mmol) and the reaction mass was heated at 55° C. for 4 h. To this reaction mass was added 1-fluoromethylcyclopropane-1-sulfonamide (6.5 g, 42.9 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene ("DBU", 6.0 mL, 43 mmol). The reaction mixture was stirred at 55° C. for 18 h. The solvent was evaporated under reduced pressure and the residue was diluted with water and acidified to pH ?2 by using aq. 1.5 N HCl solution. The precipitated solid was isolated via filtration and washed with water to afford tert-butyl (1R,2S)-1-(1-(fluoromethyl)cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropylcarbamate as off-white solid (11.5 g, 96percent). MS: MS m/z 361.4 (M+-1).
96%	With hydrogenchloride; In N,N-dimethyl-formamide;	Step 4: Preparation of tert-butyl (1R,2S)-1-(1-(fluoromethyl)cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropylcarbamate To a solution of <strong>[159622-10-3](1R,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid</strong> (7.5 g, 33 mmol) in DMF (50 mL) was added 1,1'-carbonyldiimidazole ("CDI", 10.7 g, 66.0 mmol) and the reaction mass was heated at 55° C. for 4 h. To this reaction mass was added 1-fluoromethylcyclopropane-1-sulfonamide (6.5 g, 42.9 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene ("DBU", 6.0 mL, 43 mmol). The reaction mixture was stirred at 55° C. for 18 h. The solvent was evaporated under reduced pressure and the residue was diluted with water and acidified to pH ?2 by using aq. 1.5 N HCl solutions. The precipitated solid was isolated via filtration and washed with water to afford tert-butyl (1R,2S)-1-(1-(fluoromethyl)cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropylcarbamate as off-white solid (11.5 g, 96percent). MS:MS m/z 361.4 (M+-1).

Reference： [1]Patent: US2014/127156,2014,A1 .Location in patent: Page/Page column
[2]Patent: US2015/376233,2015,A1

18
[ 201230-82-2 ]
[ 38573-88-5 ]
[ 6674-22-2 ]
12-fluoro-1,2,3,4,6,7-hexahydro-4a,7a-diazacyclohepta[de]anthracen-8(5H)-one [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 16107 - 16110

19
[ 632-24-6 ]
[ 6674-22-2 ]
2-sulfamoylbenzoate 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethylene glycol; at 13℃;	5 g (25 mmol) of <strong>[632-24-6]2-sulfamoylbenzoic acid</strong> were mixed with 5.6 g of ethyleneglycol to give a white suspension which was cooled down to 13C. 3.8 g (25 mmol) DBU were added dropwise and 19.7 g additional ethyleneglycol were then added to give a white suspension. 53 g additional ethyleneglycol were then added to give a colorless solution.13C-NMR (DMSO, 400 MHz, delta ppm): 171 .5, 166, 141 , 140.5, 132, 131 , 128, 126, 63 (ethyleneglycol), 54? 48.5, 38.5, 32.5, 29.5, 26.5, 24, 19.5.

Reference： [1]Patent: WO2017/85252,2017,A1 .Location in patent: Page/Page column 35; 36

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P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 6674-22-2 ] {[proInfo.proName]}

Quality Control of [ 6674-22-2 ]

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Calculated chemistry of [ 6674-22-2 ] Expand+

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[ 6674-22-2 ] Synthesis Path-Upstream 1~1

[ 6674-22-2 ] Synthesis Path-Downstream 1~19

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