Dimethyl itaconate 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

InChIKey

ZWWQRMFIZFPUAA-UHFFFAOYSA-N

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

HS Code 

29171900

MSDS

• Language:English Provider:Dimethyl itaconate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Dimethyl itaconate Usage And Synthesis

Chemical Properties

white crystalline low melting mass or liquid

Uses

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

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 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 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

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(617-52-7)Related Product Information

• Dimethyl carbonate
• ETHANE
• Dimethyl adipate
• Dimethyl malonate
• Dimethyl fumarate
• Dimethyl phthalate
• Dimethyl sulfate
• Itaconic acid
• Dacthal
• N,N-Dimethylformamide
• Dimethyl ether
• Dimethyl sulfoxide
• Dimethyl phosphite
• Dimethyl sebacate
• Dimethyl oxalate
• Dimethyl sulfide
• DIETHYL ITACONATE
• DIBUTYL ITACONATE