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588466

Sigma-Aldrich

Methyl α-bromoacrylate

95%

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Empirical Formula (Hill Notation):
C4H5BrO2
CAS Number:
Molecular Weight:
164.99
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

Quality Level

Assay

95%

bp

70-75 °C/48 mmHg (lit.)

density

1.556 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

COC(=O)C(Br)=C

InChI

1S/C4H5BrO2/c1-3(5)4(6)7-2/h1H2,2H3

InChI key

HVJXPDPGPORYKY-UHFFFAOYSA-N

Application

Methyl α-bromoacrylate can undergo radical copolymerization with vinyl triacetoxysilane (VTAS) in the presence of azobisisobutyronitrile as the initiator. Dibromocyclopropanation of methyl α-bromoacrylate can yield methyl 1,1,2-tribromocyclopropanecarboxylate. It may be reduced with zinc dust and deuterium oxide to synthesize. Methyl acrylate-α-d with a high isotopic purity. These may undergo conjugate addition with methoxide, thiolates, oxime anions, hydrazones and EtZnCl to afford ester enolates.

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

134.6 °F

Flash Point(C)

57 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Copolymerizations of methyl ?-bromoacrylate, 2-bromoethyl methacrylate and 2,3-dibromopropyl methacrylate with vinyltriacetoxysilane
Rao VL and Babu GN
European Polymer Journal, 26(2), 227-231 (1990)
Brief review on cyclopropane analogs: synthesis and their pharmacological applications
Ajay Kumar K, et al.
International Journal of Pharmacy and Pharmaceutical Sciences, 5(1), 467-472 (2013)
A Novel Synthesis of Methyl Acrylate-?-d and 1H Nuclear Magnetic Resonance Spectra of Its Alternating Copolymers.
Yokota K, et al.
Polymer Journal, 12(3), 177-181 (1980)
1,2,2-tribromocyclopropanecarboxylic acid and derivatives?Valuable intermediates for four carbon cyclopropane and cyclopropene synthons
Al Dulayymi AR, et al.
Tetrahedron, 52(10), 3409-3424 (1996)

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