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592498

Sigma-Aldrich

Dimethyl itaconate

99%

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Synonym(s):
2-(Methylene)butanedioic dimethyl ester
Linear Formula:
CH3O2CCH2C(=CH2)CO2CH3
CAS Number:
Molecular Weight:
158.15
Beilstein/REAXYS Number:
386674
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

99%

form

solid

bp

208 °C (lit.)

mp

37-41 °C (lit.)

density

1.124 g/mL at 25 °C (lit.)

SMILES string

COC(=O)CC(=C)C(=O)OC

InChI

1S/C7H10O4/c1-5(7(9)11-3)4-6(8)10-2/h1,4H2,2-3H3

InChI key

ZWWQRMFIZFPUAA-UHFFFAOYSA-N

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1 of 4

This Item
109533476196149012
vibrant-m

592498

Dimethyl itaconate

vibrant-m

109533

Dimethyl itaconate

vibrant-m

476196

Dibutyl itaconate

vibrant-m

149012

Dimethyl suberate

form

solid

form

solid

form

-

form

liquid

bp

208 °C (lit.)

bp

208 °C (lit.)

bp

284 °C (lit.)

bp

268 °C (lit.)

mp

37-41 °C (lit.)

mp

37-41 °C (lit.)

mp

-

mp

-

density

1.124 g/mL at 25 °C (lit.)

density

1.124 g/mL at 25 °C (lit.)

density

0.985 g/mL at 25 °C (lit.)

density

1.014 g/mL at 25 °C (lit.)

General description

Dimethyl itaconate can be synthesized via esterification of itaconic acid.

Application

Dimethyl itaconate can be used for the rhodium catalyzed asymmetric hydrogenation of (S)-dimethyl-2-methylsuccinate and (R)-methyl succinic acid dimethyl ester.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Skin Irrit. 2 - Skin Sens. 1B

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

212.0 °F - closed cup

flash_point_c

100 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)


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?Modification of poly(propylene) through grafting with dimethyl
itaconate in solution?
Yazdani-Pedram M, et al.
Macromolecular Chemistry and Physics, 199(11), 2495- 2500 (1998)
"Catalytic asymmetric hydrogenation of dimethyl itaconate with trans-chelating chiral diphosphine ligands TRAP-rhodium complexes"
Kuwano R, et al.
Tetrahedron Asymmetry, 6(10), 2521- 2526 (1995)
?New ferrocenyl ligands with broad applications in asymmetric catalysis?
Lotz M, et al.
Angewandte Chemie (International Edition in English), 41(24), 4708-4711 (2002)
Yepin Zhao et al.
Advanced materials (Deerfield Beach, Fla.), 32(17), e1907769-e1907769 (2020-03-10)
Intrinsically, detrimental defects accumulating at the surface and grain boundaries limit both the performance and stability of perovskite solar cells. Small molecules and bulkier polymers with functional groups are utilized to passivate these ionic defects but usually suffer from volatility
Vittoria Chimisso et al.
Langmuir : the ACS journal of surfaces and colloids, 35(41), 13413-13420 (2019-10-05)
Poly(N-vinylcaprolactam-co-itaconate) (P(VCL-co-IADME) microgels were synthesized varying the molar ratio between VCL and IADME via free radical precipitation polymerization in the presence of quaternary ammonium surfactant. In order to determine the effect of the divalent metal ions on the structure and

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