592498
Dimethyl itaconate
99%
Synonym(s):
2-(Methylene)butanedioic dimethyl ester
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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
Quality Level
Assay
99%
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
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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.
Signal Word
Warning
Hazard Statements
Precautionary 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
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?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?
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)
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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