2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester Chemical Properties

Melting point:

154-157 °C

Boiling point:

330°C (rough estimate)

Density 

1.3792 (rough estimate)

vapor pressure 

0-0.002Pa at 20-50℃

refractive index 

1.6000 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

form 

Fine Crystalline Powder

pka

9.04±0.40(Predicted)

color 

White to light yellow-green

Water Solubility 

Soluble in water 0.0016 g/L.

InChI

InChI=1S/C10H12O6/c1-15-9(13)5-3-8(12)6(4-7(5)11)10(14)16-2/h5-6H,3-4H2,1-2H3

InChIKey

MHKKFFHWMKEBDW-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)CC(=O)C(C(OC)=O)CC1=O

LogP

2.49 at 23℃ and pH7

CAS DataBase Reference

6289-46-9(CAS DataBase Reference)

EPA Substance Registry System

1,4-Cyclohexanedicarboxylic acid, 2,5-dioxo-, 1,4-dimethyl ester (6289-46-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-24/25

WGK Germany 

1

TSCA 

Yes

HS Code 

29145090

MSDS

• Language:English Provider:2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester Usage And Synthesis

Chemical Properties

white to light yellow-green fine cryst. powder

Uses

Dimethyl 1,4-cyclohexanedione-2,5-dicarboxylate is used in the production of pigments such as pigment red 122 and pigment violet 19. It also can react with 2,4-diamino-phenol to get 2,5-bis-(3-amino-4-hydroxy-phenylamino)-cyclohexa-1,4-diene-1,4-dicarboxylic acid dimethyl ester.

Synthesis

General procedure for the synthesis of dimethyl succinosuccinate from methyl 4-chloroacetoacetate: Under stirring conditions, methyl 4-chloroacetoacetate (10 g, 0.06 mol) was slowly added to a mixed solution containing potassium carbonate (17 g, 0.12 mol) and DMSO (50 mL). The reaction mixture was first stirred at room temperature for 3 hours, then warmed to 60 °C and continued stirring for 10 hours. After completion of the reaction, the mixture was cooled to room temperature, diluted with an appropriate amount of water and subsequently filtered. The filtrate was extracted with ether and the extract was dried over anhydrous magnesium sulfate and the solvent was removed by distillation to give a yellow crystal product (14 g, 52% yield) with a melting point of 152-153 °C. The structure of the product was confirmed by 1H NMR and 13C NMR spectra: 1H NMR (δ, ppm): 3.20 (s, 2H, CH2), 3.80 (s, 3H, CH3O), 3.90 (s, 3H, CH3O), 7.45 (s, 1H, CH=), 9.80 (s, 1H, OH), 12.10 (s, 1H, OH). 13C NMR (CDCl3, δ, ppm): 28.42, 52.33, 53.07, 95.94, 118.00, 120.05, 151.32, 168.00, 171.36. Elemental analytical results are in accordance with the theoretical values: measured (%): C 52.78, H 5.17; theoretical (C10H12O6, %): C 52.63, H 5.26.

References

[1] Russian Journal of Organic Chemistry, 2017, vol. 53, # 7, p. 1099 - 1101
[2] Zh. Org. Khim., 2017, vol. 53, # 7, p. 1084 - 1086,3

2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester(6289-46-9)Related Product Information

• Cyclohexanecarboxaldehyde
• METHYL 2-METHYLPENTANOATE
• 3-Acetyl-1-propanol
• Hexanoic acid
• Dimethyl 1,4-cyclohexanedicarboxylate
• 2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester
• METHYL 3-OXOHEPTANOATE
• 2-Methyl butyric acid
• SUCCINALDEHYDE
• Monomethyl adipate
• Methyl 3-oxovalerate
• Cyclohexanemethanol
• 2-METHYLVALERIC ACID
• Adipic acid
• 3-METHYLCYCLOHEXANONE
• 4-Heptanone
• 2-methylhexanoic acid
• Acetoacetic Acid