ChemicalBook Product Catalog Chemical Reagents Organic reagents Esters Methyl ester compound Dimethyl itaconate

Dimethyl itaconate

Product NameDimethyl itaconate
CAS617-52-7
MFC7H10O4
MW158.15
EINECS210-519-6
MOL File617-52-7.mol

Chemical Properties

Melting point	37-41 °C (lit.)
Boiling point	208 °C (lit.)
Density	1.124 g/mL at 25 °C (lit.)
vapor pressure	4.05Pa at 20℃
refractive index	1.4457 (estimate)
Flash point	213 °F
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
solubility	Chloroform (Slightly), Ethyl Acetate (Slightly)
form	Crystalline Low Melting Mass or Liquid
Specific Gravity	1.124
color	White
Water Solubility	slightly soluble
BRN	386674
Cosmetics Ingredients Functions	HAIR CONDITIONING SKIN PROTECTING SKIN CONDITIONING - MISCELLANEOUS ANTIOXIDANT
InChI	1S/C7H10O4/c1-5(7(9)11-3)4-6(8)10-2/h1,4H2,2-3H3
InChIKey	ZWWQRMFIZFPUAA-UHFFFAOYSA-N
SMILES	COC(=O)CC(=C)C(=O)OC
LogP	0.86 at 25℃
CAS DataBase Reference	617-52-7(CAS DataBase Reference)
NIST Chemistry Reference	Butanedioic acid, methylene-, dimethyl ester(617-52-7)
EPA Substance Registry System	Butanedioic acid, 2-methylene-, 1,4-dimethyl ester (617-52-7)

Safety Information

Safety Statements	24/25
WGK Germany	3
F	3
TSCA	TSCA listed
HS Code	29171900
Storage Class	11 - Combustible Solids
Hazard Classifications	Skin Irrit. 2 Skin Sens. 1B

MSDS

Provider	Language
Dimethyl itaconate	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

white crystalline low melting mass or liquid

Uses

Dimethyl itaconate can be used for the rhodium catalyzed asymmetric hydrogenation of (S)-dimethyl-2-methylsuccinate and (R)-methyl succinic acid dimethyl ester.

Uses

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).

Uses

Dimethyl Itaconate is a chemical reagent used in the synthesis of functionalized 2-isoxazolines used in fragment-based drug discovery.

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.

Flammability and Explosibility

Non flammable

Synthesis

67-56-1

97-65-4

617-52-7

1. Itaconic acid, methanol and catalyst were mixed in a certain ratio and transferred to a 100 mL autoclave. 2. The reaction mixture was continuously stirred at 120 °C. 3. Optimization of the reaction conditions was carried out by adjusting the parameters such as the molar ratio of methanol to itaconic acid, the catalyst dosage and the reaction time. 4. Upon completion of the reaction, the catalyst was separated and recovered through a filtration operation.

Purification Methods

Crystallise the ester from MeOH by cooling to -78o. [Beilstein 2 IV 2229.]

References

[1] Journal of Molecular Catalysis A: Chemical, 2013, vol. 368-369, p. 24 - 30
[2] Heterocycles, 1988, vol. 27, # 8, p. 1887 - 1898
[3] Tetrahedron Letters, 2015, vol. 56, # 27, p. 4119 - 4123
[4] Chemistry and physics of lipids, 2002, vol. 120, # 1-2, p. 9 - 20
[5] Russian Chemical Bulletin, 2005, vol. 54, # 2, p. 348 - 353

Dimethyl itaconate

Chemical Properties

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MSDS

Usage And Synthesis

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