M27301

Sigma-Aldrich

Methyl acrylate

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

Linear Formula:
CH2=CHCOOCH3
CAS Number:
Molecular Weight:
86.09
Beilstein/REAXYS Number:
605396
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.23
Pricing and availability is not currently available.

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.

Packaging

5, 250 mL in glass bottle
18 L in steel drum
1, 2 L in glass bottle

Pictograms

FlameSkull and crossbones

Signal Word

Danger

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

F,Xn

Risk Statement

11-20/21/22-36/37/38-43

Safety Statement

9-25-26-33-36/37-43

RIDADR

UN 1919 3 / PGII

WGK Germany

WGK 2

Flash Point(F)

27.0 °F - closed cup

Flash Point(C)

-2.8 °C - closed cup

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)
Rybak A and Meier MAR.
Green Chemistry, 9(12), 1356-1361 (2007)
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)
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)
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)
Articles
Our strategy is to synthesize mesoporous carbonaceous materials (“Starbons”) using mesoporous expanded starch as the precursor without the need for a templating agent.
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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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The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.
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