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302546

Sigma-Aldrich

Methyl 2-(bromomethyl)acrylate

97%

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About This Item

Linear Formula:
H2C=C(CH2Br)CO2CH3
CAS Number:
4224-69-5
Molecular Weight:
179.01
Beilstein:
1852481
MDL number:
MFCD00011697
UNSPSC Code:
12162002
PubChem Substance ID:
24858262
NACRES:
NA.23

Assay

97%

refractive index

n20/D 1.490 (lit.)

bp

35-37 °C/1.3 mmHg (lit.)

density

1.489 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

COC(=O)C(=C)CBr

InChI

1S/C5H7BrO2/c1-4(3-6)5(7)8-2/h1,3H2,2H3

InChI key

CFTUQSLVERGMHL-UHFFFAOYSA-N

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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.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315,H318,H335

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

172.4 °F - closed cup

Flash Point(C)

78 °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’.

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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)
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
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)
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
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.

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