[ CAS No. 584-08-7 ] {[proInfo.proName]}

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Quality Control of [ 584-08-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 584-08-7 ]

SDS Specification

Alternatived Products of [ 584-08-7 ]

Product Citations Expand+

MR Imaging Reveals Dynamic Aggregation of Multivalent Glycoconjugates in Aqueous Solution

Tang, Jian-Hong ; Luo, Minrui ; Tsao, Wilhelmina , et al. Inorg. Chem.,2024,63(52):24662-24671. DOI: 10.1021/acs.inorgchem.4c03878 PubMed ID: 39680369

Abstract: Glycoconjugates forming from the conjugation of carbohydrates to other biomolecules, such as proteins, lipids, or other carbohydrates, are essential components of mammalian cells and are involved in numerous biological processes. Due to the capability of sugars to form multiple hydrogen bonds, many synthetic glycoconjugates are desirable biocompatible platforms for imaging, diagnostics, drugs, and supramolecular self-assemblies. Herein, we present a multimeric galactose functionalized paramagnetic gadolinium (Gd(III)) chelate that displays spontaneous dynamic aggregation in aqueous conditions. The dynamic aggregation of the Gd(III) complex was shown by the concentration-dependent magnetic resonance (MR) relaxation measurements, nuclear magnetic resonance dispersion (NMRD) analysis, and dynamic light scattering (DLS). Notably, these data showed a nonlinear relationship between magnetic resonance relaxation rate and concentrations (0.03?1.35 mM), and a large DLS hydrodynamic radius was observed in the high-concentration solutions. MR phantom images were acquired to visualize real-time dynamic aggregation behaviors in aqueous solutions. The in situ visualization of the dynamic self-assembling process of multivalent glycoconjugates has rarely been reported.

Purchased from AmBeed: 584-08-7 ; 39224-61-8 ; 294-90-6

Highly selective catalytic transfer hydrodeuteration of cyclic alkenes

Hintzsche, Samuel J. ; Vang, Zoua Pa ; Rivera Torres, Emanuel , et al. J. Labelled Compd. Rad.,2023,66(3):86-94. DOI: 10.1002/jlcr.4015 PubMed ID: 36772856

Abstract: Selective deuterium installation into small molecules is becoming increasingly desirable not only for the elucidation of mechanistic pathways and studying biological processes but also because of deuterium's ability to favorably adjust the pharmacokinetic parameters of bioactive molecules. Fused bicyclic moieties, especially those containing heteroatoms, are prevalent in drug discovery and pharmaceuticals. Herein, we report a copper-catalyzed transfer hydrodeuteration of cyclic and heterocyclic alkenes, which enables the synthesis of chromans, quinolinones, and tetrahydronaphthalenes that are precisely deuterated at the benzylic position. We also demonstrate the ability to place one deuterium atom at the homobenzylic site of these scaffolds with high regioselectivity by swapping transfer reagents for their isotopic analogs. Furthermore, examples of chemoselective transfer hydrogenation and transfer deuteration are disclosed, allowing for the simultaneous incorporation of two vicinal hydrogen or deuterium atoms into a double bond.

Keywords: copper ; deuteration ; hydrodeuteration ; hydrogenation ; transition metal catalysis

Purchased from AmBeed: 6836-19-7 ; 14243-64-2 ; 19315-93-6 ; 1810-66-8 ; 584-08-7 ; 189114-61-2 ; 447-53-0

Product Details of [ 584-08-7 ]

CAS No. :	584-08-7	MDL No. :	MFCD00011382
Formula :	K₂CO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BWHMMNNQKKPAPP-UHFFFAOYSA-L
M.W :	138.21	Pubchem ID :	11430
Synonyms :

Calculated chemistry of [ 584-08-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	6.77
TPSA :	63.19 ?2

Pharmacokinetics

GI absorption :	Low
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) :	-7.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-0.13
Log Po/w (WLOGP) :	-2.45
Log Po/w (MLOGP) :	-1.6
Log Po/w (SILICOS-IT) :	-0.44
Consensus Log Po/w :	-0.92

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.61
Solubility :	33.5 mg/ml ; 0.243 mol/l
Class :	Very soluble
Log S (Ali) :	-0.74
Solubility :	25.0 mg/ml ; 0.181 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	1.49
Solubility :	4260.0 mg/ml ; 30.8 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.25

Safety of [ 584-08-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P501	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 584-08-7 ]

* 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 [ 584-08-7 ]
Downstream synthetic route of [ 584-08-7 ]

[ 584-08-7 ] Synthesis Path-Upstream 1~4

1
[ 1722-12-9 ]
[ 57260-73-8 ]
[ 584-08-7 ]
[ 137583-05-2 ]

Reference： [1] Patent: US6159964, 2000, A,

2
[ 181955-94-2 ]
[ 584-08-7 ]
[ 7757-82-6 ]
[ 85817-34-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium cyanoborohydride; benzaldehyde; acetic acid In tetrahydrofuran; methanol	3. 4-Benzyl-2-hydroxymethylpiperazine To a cooled (0° C.) and stirred solution of Intermediate 1 (22 g, 57 mmol), acetic acid (9.7 mL, 171 mmol) and sodium cyanoborohydride (7.16 g, 114 mmol) in methanol (440 mL) was added benzaldehyde (5.8 mL, 57 mmol). The cooling bath was removed and the mixture stirred at room temperature for 3 h. Saturated K₂ CO₃ solution (200 mL) was added and the mixture stirred for 15 min. The solvents were evaporated and the residue partitioned between CH₂ Cl₂ (2*400 mL) and water (500 mL). The combined organic layers were dried (Na₂ SO₄) and evaporated. The residue was chromatographed on silica gel, eluding with CH₂ Cl₂: MeOH (95:5) to afford an inseparable mixture of 4-benzylpiperazine-2-carboxylic acid methyl ester and the corresponding ethyl ester (5.33 g, 40percent), in a 7:1 ratio respectively. To a solution of the esters (5.33 g, 22.8 mmol) in THF (200 mL) was added LiAl H₄ (22.8 mL of a 1.0M solution in ether) dropwise at -10° C. Stirring was continued at -10° C. for 2.5 h. After this time saturated Na₂ SO₄ solution (30 mL) was added and the cooling bath removed. Stirring was continued at room temperature for 10 min then the mixture was filtered and the filtrate evaporated. The residue was chromatographed on silica gel, eluding with CH₂ Cl₂:MeOH:NH₃ (90:8:1-->60:8:1) to afford the title compound (3.7 g, 78percent) as a colourless oil. ¹ H NMR (360 MHz, CDCl₃) δ 1.89-1.95 (1H, m), 2.08-2.30 (3H, m), 2.68-2.71 (2H, m), 2.86-3.04 (3H, m), 3.45-3.60 (4H, m), 7.13-7.32 (5H, m). MS (ES⁺) 207 (M+1).

Reference： [1] Patent: US5849746, 1998, A,

3
[ 57-55-6 ]
[ 584-08-7 ]
[ 16606-55-6 ]

Reference： [1] Patent: US6054596, 2000, A,

4
[ 2457-50-3 ]
[ 7677-24-9 ]
[ 584-08-7 ]
[ 79-44-7 ]
[ 159307-02-5 ]

Reference： [1] Patent: US5350696, 1994, A,
[2] Patent: US5559214, 1996, A,
[3] Patent: US5760191, 1998, A,

[ 584-08-7 ] Synthesis Path-Downstream 1~19

1
[ 110-53-2 ]
[ 584-08-7 ]
[ 2050-94-4 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 10774 - 10777

2
[ 60-29-7 ]
[ 54550-36-6 ]
[ 403-01-0 ]
[ 584-08-7 ]
[ 117420-32-3 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; acetonitrile;	PART A -- Preparation of methyl 3-fluoro-4-[2-(2-ethoxyethoxy)-ethoxy]-benzoate. Into a 500-ml, round-bottom flask equipped with a magnetic stirrer, heating mantle and condenser were placed 5.7 g (33.5 mmol) <strong>[403-01-0]methyl 3-fluoro-4-hydroxybenzoate</strong>, 8.5 g (43.2 mmol) 1-bromo-2-(2-ethoxyethoxy)-ethane, 23.2 g of powdered anhydrous potassium carbonate and 350 ml acetonitrile. After stirring the reaction mixture under reflux for four hours, TLC analysis showed that none of the phenolic starting material remained. Three hundred ml of the acetonitrile was then distilled off and 300 ml dichloromethane was added. The reaction mixture was filtered through Celite and the solids were washed thoroughly with dichloromethane. Evaporation of the filtrate yielded product in the form of a yellow oil. Purification by flash chromatography on silica gel with 4percent ethyl ether in dichloromethane, followed by low temperature recrystallization from pentane, yielded 0.55 g of white crystals, 89percent, m.p. 33-36.5°C. The structure was confirmed by infrared, nuclear magnetic resonance and mass spectral analyses.

Reference： [1]Patent: EP258578,1993,B1

3
copper(ll) sulfate pentahydrate [ No CAS ]
[ 56525-79-2 ]
[ 629-50-5 ]
[ 3001-15-8 ]
[ 584-08-7 ]
[ 524067-29-6 ]
4,4'-Bis-[9-(3,6-diphenylcarbazolyl)]-1-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE II Synthesis of 4,4'-Bis-[9-(3,6-diphenylcarbazolyl)]-1-1,1'-biphenyl In a 50 milliliter round bottom flask there were added 4,4'-diiodo-1,1'-biphenyl (2.1 grams), 3,6-diphenyl carbazole (3.3 grams), potassium carbonate powder (1.4 grams), copper sulfate pentahydrate (0.06 grams), and 5 milliliters of tridecane. The resulting mixture was heated to 230° C. and stirred at this temperature under argon for 24 hours. After cooling to room temperature (~23° C.), the solids content resulting was ground into slurry, which slurry was then transferred to a filtration funnel, washed with hexane to remove the tridecane, followed by washing with 3 percent hydrochloric acid and water. The solid resulting was then dissolved in hot toluene. The insoluble residue was filtered hot. After cooling to room temperature, the product was crystallized from the solution to yield 2.3 grams of 4,4'-bis-[9-(3,6-diphenylcarbazolyl)]-1,1'-biphenyl as a yellowish powder. This compound had a melting point of 294° C. Its chemical structure was confirmed by proton analysis.

Reference： [1]Patent: US6562982,2003,B1

4
5-bromopyrazine-2-carboxylic acid methyl ester [ No CAS ]
[ 75-09-2 ]
[ 4214-79-3 ]
[ 584-08-7 ]
5-(5-chloro-2-oxo-2H-pyridin-1-yl)-pyrazine-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper; In 5,5-dimethyl-1,3-cyclohexadiene; ethyl acetate;	Step 2 5-(5-chloro-2-oxo-2H-pyridin-1-yl)-pyrazine-2-carboxylic acid methyl ester <strong>[4214-79-3]5-Chloro-2-pyridinol</strong> (1.43 g, 11.05 mmol), the bromide from step 1 (2.39 g, 11.05 mmol), copper (0.021 g, 0.33 mmol) and K2 CO3 (1.68 g, 12.15 mmol) were heated at 120° C. for 3 hrs. Xylene (2 ml) was added and heating was continued at 1 reflux for 2 hrs. The reaction mixture was cooled, diluted with EtOAc and water and the pH was adjusted to 9 with NH4 Cl. The aqueous layer was extracted with EtOAc (2*) and the combined organic extracts were washed with brine, dried (Na2 SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc: hexanes 20:80 to EtOAc: CH2 Cl2 10:90 gradient elution) to afford the title compound as a solid. 1 H NMR (400 MHz, CDCl3) delta 9.60 (d, J=1.3 Hz, 1H), 9.23 (d, J=1.3 Hz,1H), 8.13 (d, J=2.9 Hz,1H), 7.38(dd, J=9.8 and 2.9 Hz, 1H), 6.66(d, J=9.7 Hz, 1H) and 4.07 (s, 3H) ppm.

Reference： [1]Patent: US5939439,1999,A

5
[ 3510-66-5 ]
[ 75-09-2 ]
[ 4214-79-3 ]
[ 584-08-7 ]
[ 210037-29-9 ]

Yield	Reaction Conditions	Operation in experiment
	With copper;	Step 1 5-Chloro-5'-methyl-[1,2']bipyridinyl-2-one <strong>[4214-79-3]5-Chloro-2-pyridinol</strong> (2.26 g, 17.4 mmol), 2-bromo-5-methylpyridine (3.00 g, 17.4 mmol), copper (0.022 g, 0.35 mmol) and K2 CO3 (2.66 g, 19.2 mmol) were heated at 180° C. for 16 hrs. The brown reaction mixture was cooled, diluted with EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (2*) and the combined organic extracts were washed with brine, dried (Na2 SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc: CH2 Cl2 20:80 to 50:50 gradient elution) to afford the title compound as a white solid. 1 H NMR (400 MHz, CDCl3) delta 8.37 (s, 1H), 7.96(d, J=3.0 Hz, 1H), 7.83 (d, J=8.4 Hz, 1H), 7.65(dd, J=2.4 and 8.2 Hz, 1H), 7.32(dd, J=2.9 and 9.7 Hz, 1H), 6.61(d, J=9.7 Hz, 1H) and 2.39(s,3H)ppm.

Reference： [1]Patent: US5939439,1999,A

6
[ 18282-51-4 ]
[ 4214-79-3 ]
[ 584-08-7 ]
[ 210037-26-6 ]

Yield	Reaction Conditions	Operation in experiment
	With copper;	Step 1 5-Chloro-1-(4-hydroxymethyl-phenyl)-1H-pyridin-2-one <strong>[4214-79-3]5-Chloro-2-pyridinol</strong> (0.61 g, 4.7 mmol), 4-iodobenzyl-alcohol (1.00 g, 4.27 mmol), Copper (0.27 g, 4.27 mmol) and K2 CO3 (0.65 g, 4.70 mmol) were heated at 180° C. for 16 hrs. The brown reaction mixture was cooled, diluted with EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (2*) and the combined organic extracts were washed with brine, dried (Na2 SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc as eluent) to afford the title compound as a white solid. 1 H NMR (400 MHz, CD3 OD) delta 7.74 (d, J=2.7 Hz, 1H), 7.59 (dd, J=3.0 and 9.6 Hz, 1H), 7.51 (d, J=8.6 Hz, 2H), 7.37 (d, J=8.4 Hz, 2H), 6.61 (d, J=9.4 Hz, 1H) and 4.67(s,1H) ppm.

Reference： [1]Patent: US5939439,1999,A

7
[ 2420-16-8 ]
[ 584-08-7 ]
[ 74-88-4 ]
[ 4903-09-7 ]

Yield	Reaction Conditions	Operation in experiment
56%	In diethyl ether; acetone;	3-Chloro-4-methoxybenzaldehyde A mixture of 3-chloro-4-hydroxybenzaldehyde (25 g, 160 mmol), iodomethane (27.25 g, 192 mmol), K2 CO3 (granular, anhydrous) (110.6 g, 800 mmol), and acetone (300 mL) was refluxed for 3 hours. The reaction mixture was then cooled to room temperature. Diethyl ether (500 mL) was added and the mixture was filtered through paper to remove the inorganic solids. the filtrate was evaporated under reduced pressure, dissolved in diethyl ether (800 mL), and washed with 0.1 N NaOH (3100 mL). The organic layer was dried (Na2 SO4) and evaporated under vacuum to yield 24 g, 92percent yield of crude product. This material was further purified by chromatography on silica gel (50 mm30 cm) (elution with hexane-EtOAc, 5:1) to give 15.02 g, 56percent yield of a white solid: TLC (hexane-EtOAc, 5:1) Rf =0.24; GC Rt =4.75 min; MS (EI) m/z 170(M+), 172(M+2).
56%	In diethyl ether; acetone;	3-Chloro-4-methoxybenzaldehyde A mixture of 3-chloro-4-hydroxybenzaldehyde (25 g, 160 mmol), iodomethane (27.25 g, 192 mmol), K2 CO3 (granular, anhydrous) (110.6 g, 800 mmol), and acetone (300 mL) was refluxed for 3 hours. The reaction mixture was then cooled to room temperature. Diethyl ether (500 mL) was added and the mixture was filtered through paper to remove the inorganic solids. the filtrate was evaporated under reduced pressure, dissolved in diethyl ether (800 mL), and washed with 0.1N NaOH (3100 mL). The organic layer was dried (Na2 SO4) and evaporated under vacuum to yield 24 g, 92percent yield of crude product. This material was further purified by chromatography on silica gel (50 mm30 cm) (elution with hexane-EtOAc, 5:1) to give 15.02 g, 56percent yield of a white solid: TLC (hexane-EtOAc, 5:1) Rf =0.24; GC Rt =4.75 min; MS (EI) m/z 170(M+), 172(M+2).

Reference： [1]Patent: US6031003,2000,A
[2]Patent: US5763569,1998,A

8
CH₃ I [ No CAS ]
[ 37687-57-3 ]
[ 584-08-7 ]
[ 5417-17-4 ]

Yield	Reaction Conditions	Operation in experiment
189.49 g (96%)	With sodium hydroxide; In chloroform; water; acetonitrile;	Step 2 Synthesis of 2-chloro-3,4-dimethoxybenzaldehyde 184 g (0.986 mol) of 2-chloro-3-hydroxy-4-methoxybenzaldehyde was dissolved in 2 l of CH3 CN. 204 g (1.476 mol) of K2 CO3 and 298 g (2.096 mol) of CH3 I were added to the solution, which was heated under reflux for 4 hours. After cooling, the crystals were separated by filtration and the mother liquor was concentrated under reduced pressure. 800 ml of water and 600 ml of CHCl3 were added to the residue to conduct extraction. The CHCl3 layer was washed with 500 ml of 10percent NaOH and a saturated Nacl aqueous solution. It was dehydrated over MgSO4 and concentrated to dryness under reduced pressure to obtain 189.49 g (96percent) of 2-chloro-3,4-dimethoxybenzaldehyde. mp 70°~72° C. NMR (90 MHz, CDCl3) delta:3.88 (3H, s), 3.96 (3H, s), 6.92 (1H, d), 7.72 (1H, d), 10.28 (1H, s)

Reference： [1]Patent: US5292521,1994,A

9
[ 29882-07-3 ]
[ 584-08-7 ]
[ 57260-71-6 ]
[ 175459-01-5 ]

Yield	Reaction Conditions	Operation in experiment
42%	In water; N,N-dimethyl-formamide;	2. Intermediate 2: 4-(4-tert-Butyloxycarbonyl)piperazin-1-yl Butanal Dimethyl Acetal A mixture of <strong>[29882-07-3]4-chlorobutanal dimethyl acetal</strong> (J. Chem. Soc., Perkin Trans. 1, 1981, 251-255; 4.1 g, 26.9 mmol), K2 CO3 (4.08 g, 29.6 mmol) and tert-butyl-1-piperazinecarboxylate (5.00 g, 26.9 mmol), in anhydrous DMF (100 ml) was heated at 100° C. for 24 h. The mixture was cooled to room temperature, water (75 ml) added and extracted with ethyl acetate (5100 ml). The combined extracts were washed with water (3), dried (Na2 SO4) and evaporated. The crude product was chromatographed on silica gel eluding with ethyl acetate to give the title-product (3.41 g, 42percent). delta (250 MHz, CDCl3) 1.46 (9H, s, OC(Me)3); 1.50-1.68 (4H, m, 2 of CH2); 2.32-2.42 (6H, m, 3 of CH2); 3.30 (6H, s, (OMe)2); 3.40-3.48 (4H, m, 2 of CH2); 4.38 (1H, t, J=6 Hz, CH).

Reference： [1]Patent: US5552402,1996,A

10
[ 1634-04-4 ]
[ 6638-79-5 ]
[ 584-08-7 ]
[ 79-04-9 ]
[ 67442-07-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	In water;	EXAMPLE 7 Preparation of N-methoxy-N-methylchloroacetamide (3b). To a cold (0° C.), stirred solution of K2 CO3 (62.4 g, 450 mmol) in H2 O (250 mL) was added, successively, N,O-dimethylhydroxylamine hydrochloride (20 g, 205 mmol) and organic solvent (250 mL, toluene or MTBE). The resulting two phase mixture was cooled to -5° C. and chloroacetyl chloride (19.6 ml, 246 mmol) was added over 5 min (solution temperature maintained below 0° C.). The vigorously stirred mixture was allowed to warm to 15° C. over 30 min, the layers were separated, and the aqueous layer was extracted with organic solvent (3*100 mL, toluene or MTBE). The combined organic extracts were concentrated (MTBE used as solvent) to give the amide 3b (26.8 g, 95percent) as a white solid. Alternatively, the combined organic extracts (toluene used as solvent) were concentrated to 250 mL to effect azeotropic drying (water content 100 mug/mL) and the solution of 3b was used directly in reactions with organometallic reagents.

Reference： [1]Patent: US5786515,1998,A

11
[ 7732-18-5 ]
[ 584-08-7 ]
[ 77168-85-5 ]
5-chloro-6-methylpyrazine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%		Example 48 5-CHLORO-6-METHYL-2-PYRAZINECARBOXYLIC ACID A mixture of <strong>[77168-85-5]methyl 5-chloro-6-methyl-2-pyrazine carboxylate</strong> (0.16 g, 0.86 mmol), K2 CO3 (0.31 g, 2.18 mmol) and H2 O was stirred for 2 h at room temperature. The reaction was filtered and acidified (20percent HCl), and the resulting solid collected to provide the title compound (0.057 g, 39percent yield); m.p. 116°-117° C.

Reference： [1]Patent: US5811428,1998,A

12
[ 57616-74-7 ]
[ 584-08-7 ]
[ 118-61-6 ]
2-(3-morpholino-propoxy)-benzoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide;	(a) To a mixture of ethyl 2-hydroxybenzoate (2.4 ml, 16.38 mmol), K2 CO3 (4.98 g), and DMF (30 ml) was added <strong>[57616-74-7]N-<strong>[57616-74-7](3-chloropropyl)morpholine hydrochloride</strong></strong> (3.93 g). The mixture was stirred at room temperature for 30 minutes, then was warmed on a steam bath overnight. The reaction mixture was cooled, filtered and stripped to afford a liquid which was partitioned between EtOAc (350 ml) and water. The organic layer was separated, washed with water (2*200 ml), dried over MgSO4 and stripped to afford ethyl 2-[3-(4-morpholinyl)propoxy]benzoate.

Reference： [1]Patent: US5736548,1998,A

13
[ 3943-89-3 ]
[ 100-39-0 ]
[ 584-08-7 ]
[ 1570-05-4 ]

Yield	Reaction Conditions	Operation in experiment
101 g (92%)	With potassium hydroxide; In methanol; water; butanone;	(B) 3,4-DIBENZYLOXYBENZOIC ACID To 60 g (0.33 mole) of ethyl 3,4-dihydroxybenzoate in 50 ml of methyl ethyl ketone was added 105.5 g (0.76 mole) of K2 CO3 and 168.8 g (0.76 mole) of benzyl bromide. The mixture was refluxed for 16 hours and filtered. Evaporation of the filtration gave an oil. This oil was mixed with 40 g of KOH, 350 ml of water and 350 ml of methanol and refluxed for 2.5 hours. The methanol was evaporated and the reaction mixture was acidified with concentrated HCl. The precipitate was filtered to give 101 g (92percent) of the desired product; m.p. 184°-185° C. The NMR and IR spectra were consistent with the assigned structure.
101 g (92%)	With potassium hydroxide; In methanol; water; butanone;	3,4-Dibenzyloxybenzoic Acid To 60 g (0.33 mole) of ethyl 3,4-dihydroxybenzoate in 50 ml of methyl ethyl ketone was added 105.5 g (0.76 mole) of K2 CO3 and 168.8 g (0.76 mole) of benzyl bromide. The mixture was refluxed for 16 hours and filtered. Evaporation of the filtration gave an oil. This oil was mixed with 40 g of KOH, 350 ml of water and 350 ml of methanol and refluxed for 2.5 hours. The methanol was evaporated and the reaction mixture was acidified with concentrated HCl. The precipitate was filtered to give 101 g (92percent) of the desired product; m.p. 184°-5° C. The NMR and IR spectra were consistent with the assigned structure.
101 g (92%)	With potassium hydroxide; In methanol; water; butanone;	(b) 3,4-Dibenzyloxybenzoic Acid To 60 g (0.33 mole) of ethyl 3,4-dihydroxybenzoate in 50 ml of methyl ethyl ketone was added 105.5 g (0.76 mole) of K2 CO3 and 168.8 g (0.76 mole) of benzyl bromide. The mixture was refluxed for 16 hours and filtered. Evaporation of the filtration gave an oil. This oil was mixed with 40 g of KOH, 350 ml of water and 350 ml of methanol and refluxed for 2.5 hours. The methanol was evaporated and the reaction mixture was acidified with concentrated HCl. The precipitate was filtered to give 101 g (92percent) of the desired product; m.p. 184°-185° C. The NMR and IR spectra were consistent with the assigned structure.

Reference： [1]Patent: US4582855,1986,A
[2]Patent: US4402974,1983,A
[3]Patent: US4798892,1989,A

14
[ 61160-18-7 ]
[ 100-39-0 ]
[ 584-08-7 ]
[ 127234-68-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	In ethanol; Petroleum ether;	EXAMPLE 3a 1-(phenylmethyl)-2-methyl-3-(phenylmethoxy) 4-pyridone 73 g of the product of Example 2 were dissolved in 4 liters of ethanol (dry). 25 g K2 CO3 powderized and 70 g benzylbromide were added. After refluxing for 4 hours and filtration, the solvent was distilled off and the residue extracted with 4 liters of hot petroleum ether in 3 parts. After cooling to room temperature and filtration the petroleum ether filtrate was concentrated to 2 liters and cooled to -10° C. 31 g of white crystals of the title compound of Example 3 were obtained. The formed title compound 3A was insoluble in petroleum ether at room temperature white crystals. 70percent of total yield.

Reference： [1]Patent: US5112968,1992,A

15
[ 55453-87-7 ]
[ 584-08-7 ]
[ 96-32-2 ]
methyl-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)acetoxyacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16.5 g (94%)	In N-methyl-acetamide;	EXAMPLE 12 Methyl(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)acetoxyacetate A mixture of 15 g (0.052 m) of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid in 100 ml of dimethylformamide and 3.87 g (0.028 m) of K2 CO3 was warmed to an internal temperature of 50° C. in an atmosphere of nitrogen for 1.5 hours. To this mixture, 9.41 g (0.062 m) of methyl bromoacetate was added dropwise and the mixture was held at 50° C. overnight. The reaction mixture was poured into water and extracted with ether. The ether extract was washed with 5percent NaHCO3 and water, dried over Na2 SO4, filtered and evaporated to give 16.5 g (94percent) of an oil of methyl(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)acetoxyacetate. ANALYSIS: Calculated for C19 H16 O6: 67.05percentC; 4.74percentH; Found: 66.88percentC; 4.74percentH
16.5 g (94%)	In N-methyl-acetamide;	EXAMPLE 12 Methyl-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)acetoxyacetate A mixture of 15 g (0.052 m) of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid in 100 ml of dimethylformamide and 3.87 g (0.028 m) of K2 CO3 was warmed to an internal temperature of 50° C. in an atmosphere of nitrogen for 1.5 hours. To this mixture, 9.41 g (0.062 m) of methyl bromoacetate was added dropwise and the mixture kept at 50° C. overnight. The reaction mixture was poured into water and extracted with ether. The ether extract was washed with 5percent NaHCO3 and water, dried over Na2 SO4, filtered and evaporated to give 16.5 g (94percent) of an oil of methyl-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)acetoxyacetate. ANALYSIS: Calculated for C19 H16 O6: 67.05percentC. 4.74percentH. Found: 66.88percentC, 4.74percentH.

Reference： [1]Patent: US4576960,1986,A
[2]Patent: US4515946,1985,A

16
CH₃ I [ No CAS ]
[ 14381-51-2 ]
[ 55583-11-4 ]
[ 100-39-0 ]
[ 584-08-7 ]
[ 1838-94-4 ]
2-methyl-4-(2,4-dibenzyloxyphenyl)-2-buten-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With CuI; In acetone;	EXAMPLE 18 2-Methyl-4-(2,4-dibenzyloxyphenyl)-2-Buten-1-ol A mixture of 7.5 g (0.039 mol) of <strong>[14381-51-2]1-bromo-2,3-dihydroxybenzene</strong>, 11.2 g (0.082 mol) of K2 CO3, and 14 g (0.082 mol) of benzyl bromide in 70 ml of acetone was stirred at room temperature overnight, or until all starting material disappeared as indicated by TLC. The reaction mixture was poured into water and the aqueous solution was extracted with ether. The organic layer was separated, dried over MgSO4 and concentrated to give 14.5 g product as white solid. This compound, 1-bromo-2,4-dibenzyloxybenzene, as formed in accordance with the above procedure is conveniently summarized by the following reaction: STR9 A solution of 5.5 g (0.015 mol) of 1-bromo-2,4-dibenzyloxybenzene and 3.7 g (0.025 mol) of CH3 I in 20 ml of ether was added dropwise to 950 mg of Mg turning. The reaction mixture was refluxed for 2 hours and then cooled to -10° C. One gram of CuI was added, and stirring was continued at -10° C. for 30 min. A solution of 3.5 g (01042 mol) of 3-methyl-3,4-epoxy-1-butene in 10 ml of ether was then added dropwise to the reaction mixture, and stirring continued for another hour at -10° C. The reaction was quenced by satd. NH4 Cl solution. The organic layer was separated, dried over MgSO4 and concentrated. Purification of the crude product by dry column chromatography gave 1.6 g of product (a mixture of cis/trans isomer 8:2) as white solid; m.p. 83°-85° C. The product, 2-methyl-4-(2,4-dibenzyloxyphenyl)-2-buten-1-ol, formed from 1-homo-2,4-dibenzyloxybenzene, is conveniently depicted by the following reaction: STR10

Reference： [1]Patent: US4758586,1988,A

17
[ 503-29-7 ]
[ 29882-07-3 ]
[ 584-08-7 ]
[ 154748-48-8 ]

Yield	Reaction Conditions	Operation in experiment
	In water; N,N-dimethyl-formamide;	4-(1-Azetidinyl)butanal dimethylacetal A mixture of azetidine (2.0 g, 35.0 mmol), 4-chlorobutanal dimethylacetal (5.88 g, 39.0 mmol) and K2 CO3 (5.38 g, 39.0 mmol), in anhydrous DMF (100ml), was stirred at room temperature for 72 h. Water (50 ml) was added and the mixture extracted with EtOAc (3150 ml). The combined extracts were washed with H2 O (350ml), dried (Na2 SO4) and evaporated. The crude product was purified by distillation (1.2 g). delta (360 MHz, CDCl3) 1.35-1.42 (2H, m, CH2), 1.57-1.64 (2H, m, CH2), 2.00-2.40 (2H, m, CH2), 2.36 (2H, t, J=9.0 Hz, CH2), 3.15 (4H, m, t, J=7.0 Hz, 2 of CH2), 3.33 (6H, s, 2 of OMe), 4.35 (1H, t, J=5.7 Hz, CH).

Reference： [1]Patent: US5567726,1996,A

18
[ 584-08-7 ]
[ 4773-96-0 ]
[ 1158716-92-7 ]
[ 1158716-92-7 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water;Product distribution / selectivity;	Example 4: Preparation of <strong>[4773-96-0]mangiferin</strong> monopotassiumMangiferin 42.2(0. lmol) is suspended in the mixture of water 200ml and methanol 1800ml in reactor, mixing round adequately. Potassium carbonate 6.9g(0.05mol) is dissolved in water ,the concentration is 0.2%( w/v ) . The solution of potassium carbonate is added slowly into the <strong>[4773-96-0]mangiferin</strong> suspended solution while mixing round until the solution is clear, then the reaction solution is filtrated, appropriate quantity ethanol- chloroform (4:1 v/v) is added into the reaction solution, mixing round adequately . A lot of deposition is come into being, the reaction solution is filtrated to get the depositon, the solid substance is heated up no excess <n="12"/>60 C to dry. The yellow substance is <strong>[4773-96-0]mangiferin</strong> monopotassium. Its weight is 3 Ig, the productivity is 73.4%. The purity of <strong>[4773-96-0]mangiferin</strong> monopotassium is 98.6% detected by HPLC.

Reference： [1]Patent: WO2009/65287,2009,A1 .Location in patent: Page/Page column 10-11

19
[ 54512-75-3 ]
[ 124-38-9 ]
[ 584-08-7 ]
[ 4224-62-8 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 13426 - 13430
Angew. Chem.,2017,vol. 129,p. 13611 - 13615,5

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
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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