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Merck

M27301

Sigma-Aldrich

Methyl acrylate

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

Sinónimos:

Methylacrylate

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About This Item

Fórmula lineal:
CH2=CHCOOCH3
Número de CAS:
Peso molecular:
86.09
Beilstein/REAXYS Number:
605396
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

vapor density

3 (vs air)

Quality Level

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

signalword

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

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

27.0 °F - closed cup

flash_point_c

-2.8 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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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)
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)
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)

Artículos

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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