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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
210-519-6
Beilstein/REAXYS Number:
386674
MDL number:
Product Name
Dimethyl itaconate, 99%
InChI key
ZWWQRMFIZFPUAA-UHFFFAOYSA-N
InChI
1S/C7H10O4/c1-5(7(9)11-3)4-6(8)10-2/h1,4H2,2-3H3
SMILES string
COC(=O)CC(=C)C(=O)OC
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
Quality Level
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Application
Dimethyl itaconate can be used for the rhodium catalyzed asymmetric hydrogenation of (S)-dimethyl-2-methylsuccinate and (R)-methyl succinic acid dimethyl ester.
General description
Dimethyl itaconate can be synthesized via esterification of itaconic acid.
signalword
Warning
hcodes
Hazard Classifications
Skin Irrit. 2 - Skin Sens. 1B
Storage Class
11 - Combustible Solids
wgk
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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"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)
?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)
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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