| Identification | More | [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 Properties | Back 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 Data | Back Directory | [Hazard Codes ]
Xi | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2916200090 |
| Hazard Information | Back 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]
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 |
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