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About This Item
Linear Formula:
CH2=CHCOOCH3
CAS Number:
Molecular Weight:
86.09
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
EC Number:
202-500-6
Beilstein/REAXYS Number:
605396
MDL number:
vapor density
3 (vs air)
Quality Segment
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
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.
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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
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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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)
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)

