Skip to Content
Merck
All Photos(1)

Documents

592498

Sigma-Aldrich

Dimethyl itaconate

99%

Synonym(s):

2-(Methylene)butanedioic dimethyl ester

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
CH3O2CCH2C(=CH2)CO2CH3
CAS Number:
Molecular Weight:
158.15
Beilstein:
386674
EC Number:
MDL number:
UNSPSC Code:
12352100
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

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

Skin Irrit. 2 - Skin Sens. 1B

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

212.0 °F - closed cup

Flash Point(C)

100 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

?New ferrocenyl ligands with broad applications in asymmetric catalysis?
Lotz M, et al.
Angewandte Chemie (International Edition in English), 41(24), 4708-4711 (2002)
?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)
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
"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)
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service