302546
Methyl 2-(bromomethyl)acrylate
97%
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About This Item
Linear Formula:
H2C=C(CH2Br)CO2CH3
CAS Number:
Molecular Weight:
179.01
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1852481
InChI key
CFTUQSLVERGMHL-UHFFFAOYSA-N
InChI
1S/C5H7BrO2/c1-4(3-6)5(7)8-2/h1,3H2,2H3
SMILES string
COC(=O)C(=C)CBr
assay
97%
bp
35-37 °C/1.3 mmHg (lit.)
density
1.489 g/mL at 25 °C (lit.)
storage temp.
−20°C
Application
Methyl (2-bromomethyl)acrylate (MBrMA) may be used as chain transfer agents in the emulsion polymerization of methyl methacrylate (MMA) and styrene. MBrMA can undergo nucleophilic substitution of carboxylic acid to form methyl 2-(acyloxymethyl)acrylates.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
172.4 °F - closed cup
flash_point_c
78 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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Mukund P Sibi et al.
Tetrahedron, asymmetry, 17(4), 516-519 (2006-06-27)
We have investigated the effect of nitrogen protecting groups in radical addition trapping experiments leading to beta(2)-amino acids. Of the three N-protecting groups examined, the phthalimido group was optimal with respect to both yields and enantioselectivity. Additionally, radical additions to
Bunichiro Yamada, Shuzo Aoki, Radical polymerization and copolymerization of methyl 2-(acyloxymethyl)acrylate as hindered 2-substituted acrylate
Kobatake S, et al.
Polymer, 36(2), 413-419 (1995)
Use of methyl 2-(bromomethyl) acrylate as a chain-transfer agent to yield functionalized macromonomers via conventional and living radical polymerizations.
Bon, SAF, et al.
Macromolecules, 33(16), 5819-5824 (2000)
Fabrice Denes et al.
The Journal of organic chemistry, 72(2), 398-406 (2007-01-16)
Enantioenriched 3,4-disubstituted beta-prolines have been prepared with a high diastereocontrol through a carbometalation reaction or through a domino Michael addition/carbometalation reaction.
Thomas Mendgen et al.
Bioorganic & medicinal chemistry letters, 20(19), 5757-5762 (2010-08-24)
The enzyme MurA performs an essential step in peptidoglycan biosynthesis and is therefore a target for the discovery of novel antibacterial compounds. We report here the inhibition of MurA by natural products from tulips (tulipalines and tuliposides), and the structure-activity
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