Skip to Content
Merck
All Photos(1)

Key Documents

588466

Sigma-Aldrich

Methyl α-bromoacrylate

95%

Sign Into View Organizational & Contract Pricing


About This Item

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

134.6 °F - closed cup

Flash Point(C)

57 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service