2-Methyl-1,3-cyclopentanedione Chemical Properties

Melting point:

212-215 °C (lit.)

Boiling point:

213°C (estimate)

Density 

1.0795 (rough estimate)

refractive index 

1.4550 (estimate)

storage temp. 

Store below +30°C.

solubility 

Solubility in hot Methanol (almost transparency).

pka

10.83±0.20(Predicted)

form 

Crystalline Powder

color 

Light beige to tan

PH

2.95 at 24.7℃ and 10g/L

BRN 

1237255

InChIKey

HXZILEQYFQYQCE-UHFFFAOYSA-N

LogP

-0.8 at 30℃ and pH7.66

CAS DataBase Reference

765-69-5(CAS DataBase Reference)

NIST Chemistry Reference

1,3-Cyclopentanedione, 2-methyl-(765-69-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29142900

MSDS

• Language:English Provider:2-Methylcyclopentane-1,3-dione
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Methyl-1,3-cyclopentanedione Usage And Synthesis

Chemical Properties

LIGHT BEIGE TO TAN CRYSTALLINE POWDER

Uses

2-Methyl-1,3-cyclopentanedione was used as a reactant in the identification and characterization of benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases.

Uses

2-Methyl-1,3-cyclopentanedione hs been used to explore deoxycholic acid (DCA) induced changes in cell signaling. DCA is a secondary bile acid implicated in numerous pathological conditions. It has also been used in the synthesis of (-)-curcumanolide A and (-)-curcumalactone by aldol-lactonization.

Synthesis Reference(s)

Synthetic Communications, 19, p. 373, 1989 DOI: 10.1080/00397918908050676

Synthesis

The general procedure for the synthesis of 2-methyl-1,3-cyclopentanedione from 1,3-cyclopentanedione and tert-butyl peroxybenzoate was as follows: 1,3-cyclopentanedione (0.098 g, 1 mmol), tert-butyl peroxybenzoate (0.58 g, 3 mmol), CuCl (0.01 g, 0.1 mmol), and 2 mL of acetic acid were added to a reaction flask, and the reaction was carried out at 120 °C Reaction at 120°C. The progress of the reaction was monitored by thin layer chromatography (TLC) until the reaction was complete. After completion of the reaction, the crude product was purified by column chromatography (eluent ratio of petroleum ether:ethyl acetate = 40:1) to afford the target product 2-methyl-1,3-cyclopentanedione in 68% yield.

References

[1] Patent: CN105254483, 2016, A. Location in patent: Paragraph 0044

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