2-Methyl-1,3-cyclohexanedione Chemical Properties

Melting point:

206-208 °C (lit.)

Boiling point:

194.28°C (rough estimate)

Density 

1.0579 (rough estimate)

refractive index 

1.4660 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

methanol: 0.1 g/mL, clear

form 

Powder, Crystals or Crystalline Powder

pka

5.58±0.25(Predicted)

color 

Off-white to salmon to pale brown

Water Solubility 

INSOLUBLE

Sensitive 

Hygroscopic

BRN 

1281598

InChIKey

VSGJHHIAMHUZKF-UHFFFAOYSA-N

LogP

-0.390 (est)

CAS DataBase Reference

1193-55-1(CAS DataBase Reference)

NIST Chemistry Reference

1,3-Cyclohexanedione, 2-methyl-(1193-55-1)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

F 

3-10

HS Code 

29142900

MSDS

• Language:English Provider:2-Methyl-1,3-cyclohexanedione
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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

Description

2-methyl-1,3-Cyclohexanedione is a synthetic intermediate useful for pharmaceutical synthesis.

Chemical Properties

White to salmon powder

Uses

An important starting material, exemplified in a formal synthesis of acorone.1

Uses

2-Methylcyclohexane-1,3-dione acts as a synthetic intermediate. It is an important starting material, exemplified in a formal synthesis of acorone. It is also used in Organic Synthesis, Pharmaceuticals, Agrochemicals.

Synthesis

In a reactor equipped with a stirrer, 300 parts of methanol, 56 parts of a 50% aqueous solution of dimethylamine and 56 parts of 1,3-cyclohexanedione were added and the mixture was warmed up to 30 °C. A 37% aqueous solution of formaldehyde was added dropwise over a period of 1 hour. After addition, the reaction solution was maintained at 40°C for 3 hours. The unreacted 1,3-cyclohexanedione content was monitored by HPLC to confirm the reaction endpoint. Subsequently, 10 portions of 5% palladium-carbon catalyst were added to the reaction mixture and the reaction was carried out at 30°C and atmospheric pressure with hydrogen gas passed for 15 hours. The unreacted 2-dimethylaminomethyl-1,3-cyclohexanedione content was detected by high performance liquid chromatography to confirm the completion of the reaction. At the end of the reaction, the catalyst was removed by filtration at 30 °C, 300 parts of water were added to the filtrate, methanol was removed by distillation, and the residue was adjusted with 35% hydrochloric acid to pH 6. The precipitate was collected by filtration, washed with water and dried at 70 °C to give 54.8 parts of 2-methyl-1,3-cyclohexanedione as dry cake (yield: 87.0%). HPLC analysis showed that the purity of 2-methyl-1,3-cyclohexanedione in the dry cake was 97.2%. The melting point of the dried cake was 206°-208°C (literature value: 207°-209°C). FD-MS analysis showed that the dried cake had a peak at m/z 126, which was consistent with the theoretical molecular weight.

References

[1] Patent: US5276198, 1994, A

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