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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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About This Item

Linear Formula:
BrCH2COOCH3
CAS Number:
Molecular Weight:
152.97
Beilstein:
506256
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

Quality Level

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.)

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.

Application

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

Pictograms

CorrosionSkull and crossbones

Signal Word

Danger

Hazard Statements

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.

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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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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