588466
Methyl α-bromoacrylate
95%
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About This Item
Empirical Formula (Hill Notation):
C4H5BrO2
CAS Number:
Molecular Weight:
164.99
NACRES:
NA.23
PubChem Substance ID:
UNSPSC Code:
12162002
MDL number:
InChI key
HVJXPDPGPORYKY-UHFFFAOYSA-N
SMILES string
COC(=O)C(Br)=C
InChI
1S/C4H5BrO2/c1-3(5)4(6)7-2/h1H2,2H3
assay
95%
bp
70-75 °C/48 mmHg (lit.)
density
1.556 g/mL at 25 °C (lit.)
storage temp.
−20°C
Quality Level
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
3 - Flammable liquids
wgk
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
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)
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)
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