109533
Dimethyl itaconate
97%
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, 97%
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
97%
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 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).
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.
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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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)
M Sendra et al.
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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)
André M Charbonneau et al.
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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
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