ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE Chemical Properties

Boiling point:

84-86°C/8mm

Density 

1.10±0.1 g/cm3(Predicted)

Flash point:

84-86°C/8mm

storage temp. 

2-8°C

form 

solid

color 

Yellow

InChI

InChI=1S/C9H14F2O2/c1-2-13-8(12)7-3-5-9(10,11)6-4-7/h7H,2-6H2,1H3

InChIKey

HZZDWLBBNSDYQM-UHFFFAOYSA-N

SMILES

C1(C(OCC)=O)CCC(F)(F)CC1

CAS DataBase Reference

178312-47-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

HazardClass 

IRRITANT

HS Code 

2916200090

ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE Usage And Synthesis

Uses

4,4-Difluorocyclohexanecarboxylic Acid Ethyl Ester is used as a reactant in the preparation of antiretroviral drug Maraviroc (M193000), which is CCR-5 receptor antagonist used for the treatment of HIV.

Synthesis

General procedure for the synthesis of ethyl 4,4-difluorocyclohexanecarboxylate from ethyl cyclohexanonecarboxylate: ethyl 4-oxocyclohexanecarboxylate (5 g, 29 mmol) of the compound 4-oxocyclohexanecarboxylic acid (5 g, 29 mmol) was slowly added dropwise by dissolving DAST (7.7 mL) in 75 mL CCl4 at 0 °C. After the dropwise addition was completed, the reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the reaction was quenched by slow addition of water, the organic phase was separated, washed with water and dried with Na2SO4. Finally, purification by distillation gave ethyl 4,4-difluorocyclohexanecarboxylate as a colorless oil (4.2 g, 71% yield).

References

[1] Patent: WO2013/13188, 2013, A1. Location in patent: Paragraph 00312
[2] Patent: US9416132, 2016, B2. Location in patent: Page/Page column 134
[3] Patent: US2014/275080, 2014, A1. Location in patent: Paragraph 0427
[4] Patent: WO2018/213150, 2018, A1. Location in patent: Page/Page column 20; 21; 28
[5] Patent: US5968923, 1999, A

ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE(178312-47-5)Related Product Information

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