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109533

Dimethyl itaconate

Name: Dimethyl itaconate
Brand: ALDRICH

97%

Synonym(s):

2-(Methylene)butanedioic dimethyl ester

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About This Item

Linear Formula:

CH₃O₂CCH₂C(=CH₂)CO₂CH₃

CAS Number:

617-52-7

Molecular Weight:

158.15

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24846923

EC Number:

210-519-6

Beilstein/REAXYS Number:

386674

MDL number:

MFCD00008446

Assay:

97%

Form:

solid

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Properties

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

Description

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).

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pictograms

GHS07

signalword

Warning

hcodes

H315,H317

pcodes

P261 - P264 - P272 - P280 - P302 + P352 - P333 + P313

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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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)

Electronic Effects in Asymmetric Catalysis: Structural Studies of Precatalysts and Intermediates in Rh-Catalyzed Hydrogenation of Dimethyl Itaconate and Acetamidocinnamic Acid Derivatives Using C(2)-Symmetric Diarylphosphinite Ligands.

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

Immune-responsive gene 1 (IRG1) and dimethyl itaconate are involved in the mussel immune response.

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

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Global Trade Item Number

SKU	GTIN
109533-100G	04061838688637
109533-500G	04061838688644