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Methyl 4-bromobutyrate

Methyl 4-bromobutyrate structure

CAS No:
4897-84-1
Formula:
C5H9BrO2
Chemical Name:
Methyl 4-bromobutyrate
Synonyms:
Butanoic acid,4-bromo-,methyl ester;Butyric acid,4-bromo-,methyl ester;Methyl γ-bromobutyrate;Methyl 4-bromobutyrate;Methyl 4-bromobutanoate;4-Bromobutyric acid methyl ester;Methyl ω-bromobutyrate;4-Bromobutanoic acid methyl ester
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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Description

Clear colorless to pale yellow liquid

Methyl 4-bromobutyrate Basic Attributes

Molecular Weight：

181.03

Exact Mass：

181.03

BRN：

1745618

EC Number：

225-523-3

DSSTox ID：

DTXSID50197651

HScode：

2915900090

Characteristics

PSA：

26.3

XLogP3：

1.5

Appearance：

Clear colorless to pale yellow Liquid

Density：

1.371 g/cm³ @ Temp: 25 °C

Melting Point：

175-190 °C

Boiling Point：

186.5 °C

Flash Point：

186-187°C

Refractive Index：

1.456

Water Solubility：

H2O: insoluble

Storage Conditions：

Room temperature.

Safety Information

hazard class code：

36/37/38-22

safety instructions：

37/39-26-24/25

Marks：

Precautionary statement(s)：

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H315

GHS Classification：

|Warning|H302 (12.5%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 8 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Methyl 4-bromobutyrate Use and Manufacturing

A solution of γ-butyrolactone (25 mL, 28.0 g, 0.325 mole) in a 45percent solution of hydrogen bromide in acetic acid (75 mL) was heated for 4 h at 75° C., cooled to room temperature, treated with methanol (150 mL), and stirred overnight. Evaporation of the solvent gave a dark oil, which was dissolved in ethyl acetate (150 mL) and washed successively with saturated sodium bicarbonate (2.x.150 mL), saturated sodium chloride (150 mL), dried over anhydrous magnesium sulfate, and evaporated to yield a clear oil (48.8 g, 86percent). 1Hmr (CDCl3, δ): 3.68 (3H, s, OCH3), 3.44 (2H, t, 6.4 Hz, CH2γ), 2.51 (2H, t, 7.2 Hz, CH2α), 2.17 (2H, quintet, 6.8 Hz, CH2β). 13Cmr (CDCl3, δ): 172.96, 51.70, 32.66, 32.19, 27.70. IR (neat): 1738 cm-1. Mass spectrum (CI, m/z): 181 (M+1), 183 (M+3). Calcd. for C5H9O2Br: C, 33.17; H, 5.02. Found: C, 32.62; H, 4.85.Acetyl chloride (576 mg, 550 μL, 7.34 mmol) was added to a solution of 4-bromobutyric acid 4 (5.00 g, 30.0 mmol) in methanol (40 mL) cooled to 0 °C. The resulting solution was allowed to warm to room temperature and stirred for 18 h. The solution was evaporated under reduced pressure to yield methyl 4-bromobutanoate 5 (5.40 g, 30.0 mmol quant.) as acolourless oil, which was used without any further purificationExample 29: Synthesis of 4- (nitrooxy) butanoic acidO oNoGeneral procedure: Typical procedure: After refluxing the mixture of 4a (7.64g, 45.7mmol), methanol (78.4mL), and conc. sulfuric acid (0.77mL) for 16h under a dry argon atmosphere, it was cooled to room temperature. Then, aqueous solution of sodium bicarbonate (78mL) was added to the reaction mixture and the crude product was extracted with ethyl acetate. After washing the combined organic layer with sodium bicarbonate aqueous solution, water, and brine, it was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluted with a mixed solvent of chloroform/methanol (10/1v/v). The fraction with an R4-Bromobutanoyl chloride (3.1 ml, 25.28 mmol) was added to 15 ml of dry metanol at 04-Bromobutanoic acid (7.5 g, 45.2 mmole) was dissolved in methanol (50 mL), and then CH3SiCl(11.4 mL, 90.4 mmole) was added at 0 °C; the mixture was stirred at this temperature for 30 min andfor 72 h at 25 °C. The solvent was removed in vacuuo. The resultant residue was purified by columnchromatography (silica-gel) eluting with hexanes:ethyl acetate 90:10 to afford the title compound as acolorless oil (6.78 g, 83.4percent). 1H-NMR (CDCl3): δ 3.68 (s, 3H), 3.46 (t, J = 6.4 Hz, 2H), 2.50 (t, J = 7.2 Hz, 2H), 2.22–2.13 (m, 2H). 13C-NMR (CDCl3): δ173.11, 51.85, 32.80, 32.34, 27.87. HRMS (FAB+): m/z [M]+calcd for C5H9BrO2: 179.9786, found (M + 1): 180.9786.

Computed Properties

Molecular Weight:181.03
XLogP3:1.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:179.97859
Monoisotopic Mass:179.97859
Topological Polar Surface Area:26.3
Heavy Atom Count:8
Complexity:72.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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