[ CAS No. 5445-17-0 ] {[proInfo.proName]}

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Quality Control of [ 5445-17-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5445-17-0 ]

SDS Specification

Alternatived Products of [ 5445-17-0 ]

Product Details of [ 5445-17-0 ]

CAS No. :	5445-17-0	MDL No. :	MFCD00000143
Formula :	C₄H₇BrO₂	Boiling Point :	No data available
Linear Structure Formula :	CH₃CHBrCOOCH₃	InChI Key :	ACEONLNNWKIPTM-UHFFFAOYSA-N
M.W :	167.00	Pubchem ID :	95576
Synonyms :

Calculated chemistry of [ 5445-17-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	30.5
TPSA :	26.3 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.79
Log Po/w (XLOGP3) :	1.31
Log Po/w (WLOGP) :	0.94
Log Po/w (MLOGP) :	1.09
Log Po/w (SILICOS-IT) :	0.81
Consensus Log Po/w :	1.19

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.57
Solubility :	4.51 mg/ml ; 0.027 mol/l
Class :	Very soluble
Log S (Ali) :	-1.46
Solubility :	5.75 mg/ml ; 0.0344 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.24
Solubility :	9.68 mg/ml ; 0.0579 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.91

Safety of [ 5445-17-0 ]

Signal Word:	Danger	Class:	8,3
Precautionary Statements:	P210-P280-P370+P378-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310	UN#:	2920
Hazard Statements:	H314-H226	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 5445-17-0 ]

* 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 [ 5445-17-0 ]
Downstream synthetic route of [ 5445-17-0 ]

[ 5445-17-0 ] Synthesis Path-Upstream 1~1

1
[ 5445-17-0 ]
[ 53823-88-4 ]
[ 57837-19-1 ]

Reference： [1] Patent: US5639905, 1997, A,

[ 5445-17-0 ] Synthesis Path-Downstream 1~16

1
[ 5445-17-0 ]
[ 38870-89-2 ]
[ 80058-84-0 ]
[ 70630-25-0 ]

Reference： [1]Patent: CH607888,1978,
Chem.Abstr.,1979,vol. 90

2
[ 5445-17-0 ]
[ 603-35-0 ]
[ 2605-68-7 ]

Yield	Reaction Conditions	Operation in experiment
97%		A mixture of methyl-2-bromopropionate (S7) (2.00 mL, 17.9 mmol, 1.10 eq) and triphenylphosphine (4.27 g,16.3 mmol, 1.00 eq) in water (18.0 mL) was stirred at 70 C for 2.5 h. Both the aqueousand the organic layer still contained PPh3. The temperature was raised to 80 C and themixture was stirred for further 2 h. According to TLC, there was still a considerableamount of PPh3. Therefore, the mixture was stirred at 75 C overnight. After totally 23 hthe mixture was allowed to cool to rt. Afterwards aqueous NaOH (38 mL 1 M, 2.3 eq) wasadded, which led to the immediate precipitation of a yellow solid. The suspension wasstirred for 5 min, then CH2Cl2 (50 mL) was added and the layers were separated. Theaqueous phase was extracted with CH2Cl2 (2×50 mL), washed with brine, dried overMgSO4 and concentrated under reduced pressure. The crude was obtained as a yellow oil,which turned into a solid upon addition of pentane. The solid was washed with hexane(3×20 mL) and dried in vacuo to afford phosphonium ylide 17 (5.48 g, 97%) as a slightlyyellow powder.
91%	With potassium iodide; In water; toluene; at 70℃; for 20h;	After dissolving 5 g (19.06 mmol) of triphenylphosphine in 15 ml of toluene, an aqueous solution of 0.32 g (1.90 mmol) of potassium iodide in 15 ml of distilled water and 3.2 ml (28.6 mmol) of methyl 2-bromopropionate were added thereto. And the mixture was stirred at 70 C for 20 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, basified (pH 9) with 10 N aqueous sodium hydroxide solution, and extracted with dichloromethane. The obtained organic layer was dried over anhydrous sodium sulfate, filtered under reduced pressure, and distilled under reduced pressure. The obtained solid was washed with hexane and then filtered under reduced pressure and dried under reduced pressure to give 6.0 g (yield: 91%) of the title compound.

Reference： [1]Molecules,2020,vol. 25
[2]Patent: KR2015/77974,2015,A .Location in patent: Paragraph 0033-0034; 0053-0055
[3]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7102 - 7105
[4]Green Chemistry,2021,vol. 23,p. 9172 - 9178
[5]Helvetica Chimica Acta,1979,vol. 62,p. 1025 - 1039
[6]Tetrahedron Letters,1984,vol. 25,p. 5881 - 5884
[7]Angewandte Chemie - International Edition,2012,vol. 51,p. 9587 - 9591
Angew. Chem.,2012,vol. 124,p. 9725 - 9729,5

3
[ 5445-17-0 ]
[ 4983-28-2 ]
[ 353292-84-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide;	Intermediate Production Example 1 Production of 2-chloro-5-[1-(methoxycarbonyl)ethoxy]pyrimidine Used in Production Example 1 A mixture of 0.17 g of <strong>[4983-28-2]2-chloro-5-hydroxypyrimidine</strong>, 0.22 g of methyl 2-bromopropionate, 0.20 g of anhydrous potassium carbonate and 2.6 ml of N,N-dimethylformamide was stirred at 60° C. for 1 hour. The reaction solution was cooled to room temperature, then, poured into water, and extracted with t-butyl methyl ether. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.17 g of 2-chloro-5-[1-(methoxycarbonyl)ethoxy]pyrimidine. 1H-NMR(CDCl3/300 MHz) delta(ppm): 1.68 (d, 3H, J=6.6 Hz),3.79(s, 3H), 4.82 (q, 1H, J=6.7 Hz), 8.27(s, 2H)

Reference： [1]Patent: US6537948,2003,B1

4
NaBr-salt [ No CAS ]
[ 5445-17-0 ]
[ 18102-21-1 ]
[ 57646-35-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate;	a. N(1'-methoxycarbonyl-ethyl)-N-(furan-(2")-carbonyl)-2,3,6-trimethylaniline. A suspension of 51.5 g (0.382 mole) of 2,3,6-trimethylaniline, 35.3 g of NaHCO3 and 126 ml (1.15 moles) of 2-bromopropionic acid methyl ester is stirred for 6 hours at a bath temperature of 130 C., then cooled, filtered from NaBr-salt and distilled. Yield: 67.3 g of α-(2,3,6-trimethylanilino)propionic acid methyl ester (b.p. 144-146 C./9 Torr.)

Reference： [1]Patent: US4046911,1977,A

5
[ 5445-17-0 ]
[ 21883-13-6 ]
[ 941693-87-4 ]

Yield	Reaction Conditions	Operation in experiment
		Example 3 Methyl 3-(4-methoxy-2-methylphenyl)-2-methyl-3-oxopropanoate Methyl 2-bromopropanoate (0.3 mL) was added to anhydrous tetrahydrofuran (100 mL) of zinc powder (11 g) under argon gas atmosphere, followed by refluxing by heat for 15 minutes. 4-methoxy-2-dimethylbenzonitrile (5.0 g) was added to the resultant reaction solution, and further methyl 2-bromopropanoate (15 mL) was dropped thereinto taking 40 minutes, followed by refluxing by heat for 1 hour. The resultant reaction solution was cooled into room temperature, and was diluted with tetrahydrofuran (50 mL) and 50% potassium carbonate solution (30 mL), followed by stirring for 30 minutes. The supernatant of the reaction solution was separated, and concentrated under reduced pressure. The residual was poured to water, and was extracted with ethyl acetate. The extracted solution was washed by a saturated saline solution, and concentrated under reduced pressure after drying with anhydrous magnesium sulfate. Methanol (110 mL) and IN hydrochloric acid (33 ml) were added to the residue, and stirred at room temperature for 15 hours. The resultant reaction solution was concentrated under reduced pressure, was poured to water, and was extracted with ethyl acetate. The extracted solution was washed by a saturated solution of sodium chloride, and concentrated under reduced pressure after drying with anhydrous magnesium sulfate. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0?71:29), to thereby obtain a title compound (5.4 g) having the following physical properties. TLC: Rf 0.55 (hexane:ethyl acetate=3:1); 1H-NMR(300 MHz, CDCl3): delta 7.72 (d, J=9.3 Hz, 1H), 6.81-6.73 (m, 2H), 3.85 (s, 3H), 3.68 (d, J=0.6 Hz, 3H), 2.54 (s, 3H), 1.56 (d, J=0.6 Hz, 3H), 1.45 (dd, J=7.2, 0.3 Hz, 3H).

Reference： [1]Patent: EP1961754,2008,A1 .Location in patent: Page/Page column 20

6
[ 5445-17-0 ]
[ 4877-80-9 ]
[ 1161011-99-9 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5059 - 5062

7
[ 1075-35-0 ]
[ 5445-17-0 ]
2-(5-chloro-2-methyl-1H-indol-1-yl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%		To a 0 C. solution of 5-chloro-2-methyl-indole (0.100 g, 0.6 mmol) in DMSO (6 mL) was added portionwise potassium hydroxide (0.33 g, 6 mmol). The resulting solution was stirred at room temperature for 15 minutes. To this was added methyl-2-bromo propionate (0.1 mL, 0.9 mmol) in a single portion. The reaction mixture was stirred at room temperature for 16 h. The solution was cooled to 0 C. and quenched with water (20 mL). The mixture was extracted with CH2Cl2 (50 mL). This solution was washed with a saturated solution of ammonium chloride (2×20 mL), brine (200 mL), and dried over sodium sulfate. The solution was concentrated and the residue was purified via silica gel chromatography using 15-40% CH2Cl2 in hexanes to obtain the methyl ester as a clear oil (0.05 g, 0.21 mmol, 35% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA), m/z: M+1 obs=238; tR=3.03 min.

Reference： [1]Patent: US2008/27067,2008,A1 .Location in patent: Page/Page column 284-285

8
[ 5445-17-0 ]
[ 22717-55-1 ]
6-chloro-2-methyl-benzofuran-3-one [ No CAS ]

Reference： [1]Synthetic Communications,2012,vol. 42,p. 989 - 1001

9
[ 5445-17-0 ]
[ 22717-55-1 ]
6-chloro-2-methyl-benzofuran-3-one [ No CAS ]
[ 131210-59-8 ]
[ 1367455-91-1 ]

Reference： [1]Synthetic Communications,2012,vol. 42,p. 989 - 1001

10
[ 5445-17-0 ]
[ 22717-55-1 ]
[ 131210-59-8 ]

Reference： [1]Synthetic Communications,2012,vol. 42,p. 989 - 1001

11
[ 5445-17-0 ]
[ 41602-56-6 ]
C₁₁H₁₃NO [ No CAS ]
6-dimethylamino-3-hydroxy-2-methyl-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Chemical Sciences,2011,vol. 123,p. 459 - 466

12
[ 5445-17-0 ]
[ 100-58-3 ]
[ 28645-07-0 ]
[ 2328-26-9 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 17662 - 17668

13
[ 5445-17-0 ]
[ 2051-99-2 ]
[ 81576-55-8 ]
[ 81576-57-0 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a 50-mL two-neck round-bottom flask equipped with a cannula were added magnesium turnings (608 mg, 25 mmol), and the flask was heated at 80 C in vacuo for 1 h. A solution of the <strong>[2051-99-2]4-isobutylphenyl bromide</strong> (426 mg, 2.0 mmol) in THF (5 mL) was added dropwise over 3 min under argon. The mixture was heated at 50 C until the reaction was initiated. Additional <strong>[2051-99-2]4-isobutylphenyl bromide</strong> (1.71 g, 8.0 mmol) in THF (11.6 mL) was then added slowly via cannula over 15 min. The reaction mixture was heated at reflux for 3 h, after which a solution of 4-isobutylphenyl magnesium bromide 5 was obtained. To a separate 50-mL Schlenk tube was added anhydrous CoBr2 (21.9mg, 0.10mmol), and the tube was heated at 50C in vacuo for 2h. After cooling to room temperature, the cyclopropane-based bisoxazoline ligand 2 (0.12mmol) in THF (3mL) was added under argon. The resulting mixture was stirred for 1h at the same temperature, with 2-bromopropanoate 6 (1mmol) being added via syringe. The mixture solution was cooled to -80C, and the prepared Grignard reagent 5 (2.8mL, 0.5M in THF, 1.4mmol) was then added over 1h via syringe. The reaction mixture was stirred for another 6h at -80C and then quenched with saturated NH4Cl solution (5mL). The aqueous phase was extracted with diethyl ether (4×10mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate 100:1). 4.4.2 (S)-Methyl 2-(4-isobutylphenyl)propanoate 7b Colorless oil, 86% yield, 86:14 er. The enantiomeric ratio was determined by HPLC with a Daicel Chiralcel OJ-H column (0.5% 2-propanol in n-hexane, 0.5 mL/min, 220 nm, major tr = 16.75 min (S), minor tr = 20.48 min (R)). [alpha]D20 = +50.5 (c 1.0, CHCl3). Lit. 25 [alpha]D29 = +59.5 (c 1.1, CHCl3, 97:3 er). 1H NMR (300 MHz, CDCl3) delta: 7.21-7.18 (m, 2H), 7.09 (d, J = 8.1 Hz, 2H), 3.70 (q, J = 7.1 Hz, 1H), 3.66 (s, 3H), 2.45 (d, J = 7.2 Hz, 2H), 1.89-1.80 (m, 1H), 1.49 (d, J = 7.2 Hz, 3H), 0.90 (d, J = 6.6 Hz, 6H). 13C NMR (75 MHz, CDCl3) delta: 175.1, 140.5, 137.7, 129.3, 127.1, 51.9, 45.01, 45.00, 30.1, 22.3, 18.6. HRMS (APCI-TOF): calcd for C14H21O2 [M+H]+ 221.1542, found 221.1549.

Reference： [1]Tetrahedron Asymmetry,2016,vol. 27,p. 663 - 669

14
[ 5445-17-0 ]
[ 38111-44-3 ]
[ 28645-07-0 ]
[ 2328-26-9 ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 2059 - 2064

15
[ 5445-17-0 ]
[ 24388-23-6 ]
[ 28645-07-0 ]
[ 2328-26-9 ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 1128 - 1131

16
[ 5445-17-0 ]
[ 120068-37-3 ]
C₁₆H₉ClF₆N₄O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate; In acetonitrile; at 50℃;	General procedure: dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitrile was added.0.275 mmol of dimethyl butenedioate,The reaction was carried out under the conditions of Table 1. After the reaction was completed, it was cooled to room temperature.Add water and extract three times with ethyl acetate.Dried over anhydrous magnesium sulfate,The solvent was removed by filtration under reduced pressure.Separated and purified by column chromatography,Get the product,The column chromatography eluate used was a petroleum ether:ethyl acetate mixed solvent in a volume ratio of 10:1 to 5:1.

Reference： [1]Patent: CN109761989,2019,A .Location in patent: Paragraph 0052; 0053; 0055; 0059; 0060; 0062

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? General Reactivity ? Grignard Reaction ? Heat of Combustion ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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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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[ CAS No. 5445-17-0 ] {[proInfo.proName]}

Quality Control of [ 5445-17-0 ]

Related Doc. of [ 5445-17-0 ]

Product Details of [ 5445-17-0 ]

Calculated chemistry of [ 5445-17-0 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 5445-17-0 ]

Application In Synthesis of [ 5445-17-0 ]

[ 5445-17-0 ] Synthesis Path-Upstream 1~1

[ 5445-17-0 ] Synthesis Path-Downstream 1~16

Technical Information

Related Functional Groups of [ 5445-17-0 ]

Aliphatic Chain Hydrocarbons

Bromides

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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[ 5445-17-0 ]