Dimethyl glutaconate Chemical Properties

Boiling point:

192.8±15.0 °C(Predicted)

Density 

1.124 g/mL at 20 °C (lit.)

refractive index 

n20/D 1.452

Flash point:

>100 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

color 

Colourless

BRN 

1724169

NIST Chemistry Reference

2-Pentenedioic acid, dimethyl ester(5164-76-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

Dimethyl glutaconate Usage And Synthesis

Uses

Dimethyl glutaconate may be used in the synthesis of:

• dimethyl 3-[(Z)-1-propenyl]glutarate
• phenanthridinone derivatives
• substituted benzenes

General Description

Dimethyl glutaconate, also known as dimethyl 2-pentenoate, is a diester. It reacts with salicaldehyde in the presence of piperidine to form a coumarin-fused electron deficient diene.

Synthesis

Methanol (10.0 kg, 3.1 kmol), pent-2-enoic acid (5.57 kg, 0.043 kmol), and concentrated sulfuric acid (72.0 g) were sequentially added to a 20 L enameled reactor equipped with a mechanical stirrer and a thermometer. The reaction mixture was heated to reflux for the reaction. After completion of the reaction, methanol was recovered by distillation under reduced pressure. After the temperature was lowered to 20 °C, the reaction solution was washed with aqueous sodium carbonate to neutralize the acid and subsequently dried. Finally, the product was purified by vacuum distillation to give 6.22 kg of colorless liquid dimethyl pent-2-enoate in 91.5% yield and 81.6% total yield. The product was analyzed by gas chromatography (GC) with a purity of 98.8% (22.4% cis-isomer and 76.4% trans-isomer).

References

[1] Chemical Communications, 2015, vol. 51, # 77, p. 14505 - 14508
[2] Patent: CN108358783, 2018, A. Location in patent: Paragraph 0032; 0035
[3] Tetrahedron, 1992, vol. 48, # 46, p. 10103 - 10114

Dimethyl glutaconate(5164-76-1)Related Product Information

• Dimethyl fumarate
• Dimethyl sulfoxide
• Dimethyl sulfate
• Dimethyl sebacate
• Dimethyl sulfide
• Dacthal
• Dicyclopentadiene
• N,N-Dimethylformamide
• ETHANE
• 1,3-Cyclopentadiene
• TRANS-1,3-PENTADIENE
• METHYLCYCLOPENTADIENE DIMER
• Dimethyl ether
• Dimethyl carbonate
• Dimethyl suberate
• 1,2-PENTADIENE
• PENT-4-ENYLAMINE HYDROCHLORIDE
• ETHYL 2-PENTYNOATE