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588466

Sigma-Aldrich

Methyl α-bromoacrylate

95%

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About This Item

Empirical Formula (Hill Notation):
C4H5BrO2
CAS Number:
4519-46-4
Molecular Weight:
164.99
MDL number:
MFCD08276754
UNSPSC Code:
12162002
PubChem Substance ID:
24881219
NACRES:
NA.23

Quality Level

100

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

Related Categories

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
GHS02,GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

134.6 °F - closed cup

flash_point_c

57 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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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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)
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)
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)
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)

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