Ethyl 4,4-difluorocyclohexanecarboxylate

Base Information

• Chemical Name: Ethyl 4,4-difluorocyclohexanecarboxylate
• CAS No.: 178312-47-5
• Molecular Formula: C9H14F2O2
• Molecular Weight: 192.206
• Hs Code.: 2916209090
• European Community (EC) Number: 674-534-3
• DSSTox Substance ID: DTXSID20381287
• Nikkaji Number: J2.191.564E
• Wikidata: Q72474347
• Mol file: 178312-47-5.mol

Synonyms:Ethyl 4,4-difluorocyclohexanecarboxylate;178312-47-5;Ethyl 4,4-difluorocyclohexane-1-carboxylate;cyclohexanecarboxylic acid, 4,4-difluoro-, ethyl ester;ETHYL4,4-DIFLUOROCYCLOHEXANECARBOXYLATE;ethyl 4,4-difluorocyclohexane carboxylate;MFCD03788494;4,4-Difluoro-cyclohexanecarboxylic acid ethyl ester;ethyl-4,4-difluorocyclohexane carboxylate;C9H14F2O2;SCHEMBL103276;DTXSID20381287;BCP05938;BBL103251;STL557061;4-carbethoxy-1,1-difluorocyclohexane;1-carboethoxy-4,4-difluorocyclohexane;AKOS005063515;CS-W003100;DS-1550;PB20846;PS-6331;ethyl 4,4-difluoro-cyclohexanecarboxylate;SY018964;AM20070461;FT-0626055;4,4-difluorocyclohexanecarboxylic acid ethyl ester;J-521321

Chemical Property of Ethyl 4,4-difluorocyclohexanecarboxylate

Chemical Property:

• Vapor Pressure: 0.28mmHg at 25°C
• Refractive Index: 1.417
• Boiling Point: 203.3 °C at 760 mmHg
• Flash Point: 74.9 °C
• PSA: 26.30000
• Density: 1.1 g/cm³
• LogP: 2.37500
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 192.09618601
• Heavy Atom Count: 13
• Complexity: 182

Purity/Quality:

98%, ^*data from raw suppliers

4,4-DifluorocyclohexanecarboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CCC(CC1)(F)F
• 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.

Technology Process of Ethyl 4,4-difluorocyclohexanecarboxylate

There total 14 articles about Ethyl 4,4-difluorocyclohexanecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4) → ethyl 4-fluorocyclohex-3-ene-1-carboxylate (452333-58-3) + ethyl 4,4-difluorocyclohexane-1-carboxylate (178312-47-5)

Guidance literature:

With (4-(tert-butyl)-2,6-dimethylphenyl)trifluoro-λ⁴-sulfane; ethanol; In dichloromethane; at 20 ℃; for 24h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/ja106343h

Reference yield: 71.0%

ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4) → ethyl 4,4-difluorocyclohexane-1-carboxylate (178312-47-5)

Guidance literature:

With diethylamino-sulfur trifluoride; In tetrachloromethane; at 0 - 20 ℃; for 16h;

Reference yield: 38.5%

ethyl 4-(hydroxyimino)cyclohexane-1-carboxylate (90942-89-5) → ethyl 4,4-difluorocyclohexane-1-carboxylate (178312-47-5)

Guidance literature:

With pyridine; hydrogen fluoride; nitrosonium tetrafluoroborate; at 0 ℃;

ethyl 4-(hydroxyimino)cyclohexane-1-carboxylate; at -7 - 27 ℃; for 5h; Product distribution / selectivity;

upstream raw materials:

ethyl 4-oxocyclohexane-1-carboxylate

ethyl 4-(hydroxyimino)cyclohexane-1-carboxylate

ethyl 4,4-dichlorocyclohexanecarboxylate

4-chloro-cyclohex-3-enecarboxylic acid ethyl ester

Downstream raw materials:

4,4-difluorocyclohexanecarboxylic acid

(4,4-difluorocyclohexyl)methanol

4,4-difluoro-N-[(1S)-3-[(1R,5S)-3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide

4,4-difluorocyclohexane-1-carbonyl chloride

Refernces

• 1、 -. "SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF". Page/Page column 65. . Retrieved 2018/03/09.
• 2、 -. "A 4, 4 - difluoro-cyclohexyl preparation of formic acid method". Paragraph 0029; 0030; 0031. . Retrieved 2017/08/25.