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157910

Sigma-Aldrich

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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25 G
€28.90
100 G
€90.20

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Estimated to ship onApril 01, 2025

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25 G
€28.90
100 G
€90.20

About This Item

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

€28.90

Estimated to ship onApril 01, 2025

Request a Bulk Order

Quality Level

200

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

SMILES string

COC(=O)CBr

InChI

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

InChI key

YDCHPLOFQATIDS-UHFFFAOYSA-N

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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.[1]

Application

Methyl bromoacetate was used in the synthesis of novel coumarins.[2] It was also employed in the synthesis of cis-cyclopropanes.[3]

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H314,H317

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

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Certificates of Analysis (COA)

Lot/Batch Number
STBL2705
STBL2703
STBL1492
STBF3104V
STBB7312V

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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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