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109533

Sigma-Aldrich

Dimethyl itaconate

97%

Sinónimos:

2-(Methylene)butanedioic dimethyl ester

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About This Item

Fórmula lineal:
CH3O2CCH2C(=CH2)CO2CH3
Número de CAS:
617-52-7
Peso molecular:
158.15
Beilstein/REAXYS Number:
386674
EC Number:
210-519-6
MDL number:
MFCD00008446
UNSPSC Code:
12352100
PubChem Substance ID:
24846923
NACRES:
NA.22

Quality Level

100

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

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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
GHS07

signalword

Warning

hcodes

H315,H317

Hazard Classifications

Skin Irrit. 2 - Skin Sens. 1B

Storage Class

11 - Combustible Solids

wgk_germany

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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Certificados de análisis (COA)

Lot/Batch Number
BCCF6700
BCCD7456
BCCB5168
BCCB1591
BCBX3855

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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)
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)
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
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