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Merck
CN

157910

Methyl bromoacetate

97%

Synonym(s):

2-Bromoacetic acid methyl ester, Bromoacetic acid methyl ester, Carbomethoxymethyl bromide, Methyl α-bromoacetate, Methyl 2-bromoacetate, Methyl 2-bromoethanoate

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About This Item

Linear Formula:
BrCH2COOCH3
CAS Number:
96-32-2
Molecular Weight:
152.97
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24849708
EC Number:
202-499-2
Beilstein/REAXYS Number:
506256
MDL number:
MFCD00000189

Key Documents

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Product Name

Methyl bromoacetate, 97%

InChI key

YDCHPLOFQATIDS-UHFFFAOYSA-N

InChI

1S/C3H5BrO2/c1-6-3(5)2-4/h2H2,1H3

SMILES string

COC(=O)CBr

assay

97%

form

liquid

refractive index

n20/D 1.458 (lit.)

bp

51-52 °C/15 mmHg (lit.)

density

1.616 g/mL at 25 °C (lit.)

functional group

bromo
ester

Quality Level

200

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Application

Methyl bromoacetate was used in the synthesis of novel coumarins. It was also employed in the synthesis of cis-cyclopropanes.

General description

Methyl bromoacetate is an α-bromo ester. Reactions of the methyl bromoacetate with conjugate base of (methylmethoxycarbene)pentacarbonylchromium(0) yields alkylated carbene complexes.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1 - Skin Corr. 1C - Skin Sens. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

147.2 °F - closed cup

flash_point_c

64 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SDBB6610
SDBB2908
STBL2705
STBL2703
STBL1492

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Reactions of conjugate bases of metal carbene complexes with expoxides and with a-bromo esters.
Casey CP and Anderson RL.
Journal of Organometallic Chemistry, 73(2), C28-C30 (1974)
Yasameen K Al-Majedy et al.
Molecules (Basel, Switzerland), 19(8), 11791-11799 (2014-08-12)
Some novel coumarins were synthesized starting from 4-hydroxycoumarin and methyl bromoacetate. The structures of the newly obtained compounds were confirmed by elemental analysis, mass, IR and NMR spectra.
One-pot method for stereoselective cyclopropanation of electron-deficient olefins with methyl bromoacetate and phenacyl bromide in the presence of triphenylarsine.
Ren Z, et al.
Synthesis, 2005(16), 2718-2722 (2005)
Hailemichael Ayalew et al.
Polymers, 11(4) (2019-04-13)
Deprotonation-induced conductivity shift of poly(3,4-ethylenedixoythiophene)s (PEDOTs) in aqueous solutions is a promising platform for chemical or biological sensor due to its large signal output and minimum effect from material morphology. Carboxylic acid group functionalized poly(Cn-EDOT-COOH)s are synthesized and electrodeposited on
Josef Dib et al.
Journal of mass spectrometry : JMS, 50(2), 407-417 (2015-03-25)
AdipoR agonists are small, orally active molecules capable of mimicking the protein adiponectin, which represents an adipokine with antidiabetic and antiatherogenic effects. Two adiponectin receptors were reported in the literature referred to as adipoR1 and adipoR2. Activation of these receptors

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