Skip to Content
Merck
All Photos(1)

Key Documents

109533

Sigma-Aldrich

Dimethyl itaconate

97%

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

97%

form

solid

bp

208 °C (lit.)

mp

37-41 °C (lit.)

density

1.124 g/mL at 25 °C (lit.)

functional group

ester

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 undergoes enantioselective Rh(I)-catalyzed hydrogenation which can be enhanced by appropriate choice of substituents on aromatic ring of (1,2-diarylphosphinoxy)cyclohexane.

Application

Dimethyl itaconate may be used in functionalization of isotactic poly(propylene). It was used in crosslinking of polyesters: poly(isosorbide itaconate)and poly(isosorbide itaconate-co-succinate).

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

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

Visit the Document Library

M Sendra et al.
Fish & shellfish immunology, 106, 645-655 (2020-08-18)
Immune-responsive gene 1 (irg1) is a gene that is well-conserved among different taxa and is highly expressed in the mussel Mytilus galloprovincialis at the constitutive level. The expression of this gene increases after a bacterial infection, primarily in haemocytes. irg1
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)
T. V. RajanBabu et al.
The Journal of organic chemistry, 64(10), 3429-3447 (2001-10-25)
Enantioselectivity of Rh(I)-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives and dimethyl itaconate can be enhanced by the appropriate choice of substituents on the aromatic rings of vicinal diarylphosphinites derived from carbohydrates as well as trans-cyclohexane-1,2-diol. For example, the use of
Polymers with shape memory effect from renewable resources: crosslinking of polyesters based on isosorbide, itaconic acid and succinic acid.
Goerz O and Ritter H.
Polymer International, 62(5), 709-712 (2013)
André M Charbonneau et al.
Materials (Basel, Switzerland), 13(21) (2020-11-01)
The egg yolk plasma (EYP)-a translucent fraction of the egg yolk (EY) obtained by centrifugation-was tested as a developmentally encouraging, cost-effective, biomaterial for salivary gland (SG) tissue engineering. To find optimal incubating conditions for both the human NS-SV-AC SG acinar

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