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M27301

Sigma-Aldrich

Methyl acrylate

99%, contains ≤100 ppm monomethyl ether hydroquinone as inhibitor

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Synonym(s):
Methylacrylate
Linear Formula:
CH2=CHCOOCH3
CAS Number:
Molecular Weight:
86.09
Beilstein:
605396
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.23

vapor density

3 (vs air)

vapor pressure

67.5 mmHg ( 20 °C)

Assay

99%

form

liquid

autoignition temp.

874 °F

contains

≤100 ppm monomethyl ether hydroquinone as inhibitor

expl. lim.

14.5 %

refractive index

n20/D 1.402 (lit.)

bp

80 °C (lit.)

mp

−75 °C (lit.)

density

0.956 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

COC(=O)C=C

InChI

1S/C4H6O2/c1-3-4(5)6-2/h3H,1H2,2H3

InChI key

BAPJBEWLBFYGME-UHFFFAOYSA-N

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General description

Methyl acrylate is an acrylic monomer. It is useful in the preparation of polymers having rigid, flexible, ionic, nonionic, hydrophobic, or hydrophilic properties. Mechanism of the copolymerization of ethylene and α-olefins with methyl acrylate has been studied. Heck reaction of iodobenzene with methyl acrylate in the presence of triethylamine and sodium carbonate has been reported. The reversible addition fragmentation chain transfer (RAFT) bulk polymerization of methyl acrylate using 1-phenylethyl dithiobenzoate and 2-(2-cyanopropyl) dithiobenzoate (RAFT agents) has been studied. Reactive intermediates formed during the Heck reaction of methyl acrylate have been characterized by NMR spectroscopy.

Application

Methyl acrylate was used in the preparation of poly(methyl acrylate) elastomers. It was also used in the synthesis of α,ω-dicarboxylic acid esters.

Pictograms

FlameSkull and crossbones

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

27.0 °F - closed cup

Flash Point(C)

-2.8 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Origin of inhibition effects in the reversible addition fragmentation chain transfer (RAFT) polymerization of methyl acrylate.
Perrier S, et al.
Macromolecules, 35(22), 8300-8306 (2002)
Effects of dispersion and aggregation of silica in the reinforcement of poly (methyl acrylate) elastomers.
Pu Z, et al.
Chemistry of Materials, 9(11), 2442-2447 (1997)
Mechanistic studies of the palladium-catalyzed copolymerization of ethylene and a-olefins with methyl acrylate.
Mecking S, et al.
Journal of the American Chemical Society, 120(5), 888-899 (1998)
Rybak A and Meier MAR.
Green Chemistry, 9(12), 1356-1361 (2007)
Characterization of Reactive Intermediates in Palladium-Catalyzed Arylation of Methyl Acrylate (Heck Reaction).
Brown JM and Hii KKM.
Angewandte Chemie (International Edition in English), 35(6), 657-659 (1996)

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RAFT (Reversible Addition Fragmentation chain Transfer) polymerization is a reversible deactivation radical polymerization (RDRP) and one of the more versatile methods for providing living characteristics to radical polymerization.

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