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133973

Sigma-Aldrich

Ethyl bromoacetate

reagent grade, 98%

Synonym(s):

Bromoacetic acid ethyl ester, Ethyl 2-bromoacetate

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About This Item

Linear Formula:
BrCH2COOC2H5
CAS Number:
105-36-2
Molecular Weight:
167.00
Beilstein:
506456
EC Number:
203-290-9
MDL number:
MFCD00000191
UNSPSC Code:
12352100
PubChem Substance ID:
24848125
NACRES:
NA.22

grade

reagent grade

vapor pressure

2.6 mmHg ( 25 °C)

Assay

98%

form

liquid

refractive index

n20/D 1.451 (lit.)

bp

159 °C (lit.)

solubility

water: insoluble

density

1.506 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)CBr

InChI

1S/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3

InChI key

PQJJJMRNHATNKG-UHFFFAOYSA-N

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General description

Ethyl bromoacetate is commonly used in organic synthesis as an alkylating agent and acylation reagent. Ethyl bromoacetate on derivatisation reaction with p-t-butyl calix[4]arene yields 1,3-diester substituted calix[4]arene. It also undergoes Suzuki type cross-coupling reactions with arylboronic acids cocatalyzed by copper(I) oxide.

Application

Ethyl bromoacetate was used to prepare reversibly photoresponsive coumarin-stabilized polymeric nanoparticles in an aqueous medium, which act as a detectable drug carrier.

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Statements

H226,H300 + H310 + H330

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

116.6 °F - closed cup

Flash Point(C)

47 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Gillian McMahon et al.
Talanta, 57(6), 1119-1132 (2008-10-31)
A series of derivatisation reactions between p-t-butyl calix[4]arene and ethyl bromoacetate were carried out in order to prepare 1,3 diester substituted calix[4]arene. Mass spectral data, obtained from direct injection of samples, indicated that the reactions were rich in the desired
Jae Woo Chung et al.
Small (Weinheim an der Bergstrasse, Germany), 8(11), 1693-1700 (2012-03-29)
The ability to create aqueous suspended stable nanoparticles of the hydrophobic homopolymer poly(ϵ-caprolactone) end-functionalized with coumarin moieties (CPCL) is demonstrated. Nanoparticles of CPCL are prepared in a continuous manner using nanoprecipitation. The resulting nanoparticles are spherical in morphology, about 40
Unusual pathway of alkylation of 2-(4-bromobenzylidene)-p-menthan-3-one with ethyl bromoacetate
AI Krivoshei, et al.
Russian Chemical Bulletin, 56, 2506-2509 (2007)
Synthesis and cytotoxicity of 28-carboxymethoxy lupane triterpenoids. Preference of 28-O-acylation over 28-O-alkylation of betulin by ethyl bromoacetate
AA Mar, et al.
Chinese Chemical Letters = Zhongguo Hua Xue Kuai Bao, 20, 1141-1144 (2009)
A M Seldes et al.
Steroids, 39(2), 181-190 (1982-02-01)
Reformatsky reaction of 3beta, 21-diacyloxy-and 3beta-methoxy-21-acyloxy-5-pregnen-20-one with ethyl bromoacetate yields, through an intramolecular 1,2-acyl migration, 38, 20 XI-acyloxy-14alpha-card-5-enolides were converted into the respective 20 XI-hydroxy-14alpha-card-5-enolides and the 14 alpha-carda-5,20(22)-dienolides. Experimental support to the proposed intramolecular 1,2-acyl migration is provided by
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