3042-81-7

Basic information

• Product Name: METHYL ALPHA-BROMOPHENYLACETATE
• Synonyms: Methyl α-broMo acid;Methyl alpha-bromophenylacetate 97%;-Bromophenylacetate;Methyl α(R,S)-Bromo-phenyl-aceticacidmethylester;a-Bromophenylaceticacidmethylester;Benzeneaceticacid,a-bromo-,methylester;Benzeneaceticacid,α-bromo-,methylester
• CAS NO: 3042-81-7
• Molecular Formula: C9H9BrO2
• Molecular Weight: 229.07
• EINECS: 1312995-182-4
• Product Categories: Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Aromatic Phenylacetic Acids and Derivatives;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 3042-81-7.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 113 °C3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.46 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00579mmHg at 25°C
• Refractive Index: n20/D 1.554
• Storage Temp.: 2-8°C
• BRN: 1102743
• CAS DataBase Reference: METHYL ALPHA-BROMOPHENYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL ALPHA-BROMOPHENYLACETATE(3042-81-7)
• EPA Substance Registry System: METHYL ALPHA-BROMOPHENYLACETATE(3042-81-7)

Safety Data

• Hazard Codes: C
• Statements: 36/37/38-34
• Safety Statements: 26-36/39-45-36/37/39
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 3042-81-7(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow to yellow liquid

Uses

Methyl α-bromophenylacetate may be used as initiator during ESR study of atom transfer radical polymerization (ATRP) of methyl methacrylate (MMA) and ethylene glycol dimethacrylate (EGDMA). It may be used as reagent in the homopolymerization of MMA in supercritical carbon dioxide.

Synthesis Reference(s)

Tetrahedron, 42, p. 2275, 1986 DOI: 10.1016/S0040-4020(01)90607-6

General Description

Methyl α-bromophenylacetate is an ester. Palladium catalyzed homocoupling reaction of methyl α-bromophenylacetate with 3,5-dimethyl phenyl boronic acid is reported.

InChI:InChI=1/C9H9BrO2/c1-12-9(11)8(10)7-5-3-2-4-6-7/h2-6,8H,1H3/t8-/m1/s1

Upstream product

• 67-56-1 methanol 
• 19078-72-9 bromo(phenyl)acetyl chloride 
• 103-82-2 phenylacetic acid 
• 13049-41-7 1,1-dimethoxy-2-phenylethene 
• 59176-57-7 (Z)-1-phenylthio-1-trimethylsilyl-2-phenylethylene 
• 33512-02-6 3-phenyl-2,2-oxiranedicarbonitrile 
• 101-41-7 benzeneacetic acid methyl ester 
• 4358-87-6 (RS)-methyl mandelate 
• 103-80-0 phenylacetyl chloride 
• 100-52-7 benzaldehyde 
• 611-71-2 MANDELIC ACID 
• 4870-65-9 2-bromophenylacetic acid 
• 2835-06-5 phenylglycin 
• 181026-82-4 1,1-bis(trimethylsilyloxy)-2-bromo-2-phenylethene 

Downstream Products

• 109938-17-2 (2,5-dimethyl-4-oxo-piperidino)-phenyl-acetic acid methyl ester 
• 69880-97-3 (R)-((1R)-3-benzyl-7-oxo-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-phenyl-acetic acid methyl ester 
• 60190-92-3 methyl 2-(dimethoxyphosphoryl)-2-phenylacetate 
• 25169-81-7 meso-2,3-diphenylsuccinic acid dimethyl ester 
• 19020-59-8 dl-2,3-diphenylsuccinic acid dimethyl ester 
• 32121-42-9 methyl α-phenyl-α-(p-tolylthio)acetate 
• 32121-36-1 methyl 2-(naphthalen-2-yloxy)-2-phenylacetate 
• 32191-58-5 (2,4-Dichloro-phenoxy)-phenyl-acetic acid methyl ester 
• 32191-61-0 (3-Hydroxy-phenoxy)-phenyl-acetic acid methyl ester 
• 32191-46-1 methyl 2-phenoxy-2-phenylacetate 
• 60686-79-5 (R)-2-bromo-2-phenylacetic acid 
• 60686-78-4 (+)-(S)-α-bromophenylacetic acid 
• 3042-81-7 (S)-(+)-methyl 2-bromo-2-phenylacetate 
• 3042-81-7 methyl (α-bromo)phenylacetate 

Relevant articles and documents

Dynamic kinetic resolution in the hydrolysis of an α-bromo ester

Bromide can be employed to racemise an α-bromo ester more rapidly than the corresponding acid (carboxylate), and this rate difference has been employed as the basis of a dynamic kinetic resolution reaction.

Manganese/bipyridine-catalyzed non-directed C(sp3)–H bromination using NBS and TMSN3

A Mn(II)/bipyridine-catalyzed bromination reaction of unactivated aliphatic C(sp3)?H bonds has been developed using N-bromosuccinimide (NBS) as the brominating reagent. The reaction proceeded in moderate-to-good yield, even on a gram scale. The introduced bromine atom can be converted into fluorine and allyl groups.

Bromination of α-Diazo Phenylacetate Derivatives Using Cobalt(II) Bromide

A method for the bromination of α-diazo phenylacetate derivatives using cobalt(II) bromide is described. This bromination reaction features a short reaction time, broad substrate scope, operational simplicity, acid-free conditions, and gram-scalability. (Figure presented.).