ChemicalBook--->CAS DataBase List--->178312-47-5

178312-47-5

178312-47-5 Structure

178312-47-5 Structure
IdentificationMore
[Name]

ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE
[CAS]

178312-47-5
[Synonyms]

ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE
Ethyl 4,4-difluorocyclohexanedicarboxylate
Cyclohexanecarboxylic acid, 4,4-difluoro-, ethyl ester (9CI)
Cyclohexanecarboxylic acid, 4,4-difluoro-, ethyl ester
[EINECS(EC#)]

674-534-3
[Molecular Formula]

C9H14F2O2
[MDL Number]

MFCD03788494
[Molecular Weight]

192.2
[MOL File]

178312-47-5.mol
Chemical PropertiesBack Directory
[Boiling point ]

84-86°C/8mm
[density ]

1.10±0.1 g/cm3(Predicted)
[Fp ]

84-86°C/8mm
[storage temp. ]

Sealed in dry,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 DataBack Directory
[Hazard Codes ]

Xi
[Safety Statements ]

S24/25:Avoid contact with skin and eyes .
[Hazard Note ]

Irritant
[HazardClass ]

IRRITANT
[HS Code ]

2916200090
Hazard InformationBack Directory
[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]

Ethyl 4-oxocyclohexanecarboxylate

17159-79-4

ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE

178312-47-5

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
Spectrum DetailBack Directory
[Spectrum Detail]

ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE(178312-47-5)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

Ethyl 4,4-difluorocyclohexanecarboxylate, 97%(178312-47-5)
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