4,4-Difluorocyclohexane-1-carbonyl chloride

Base Information

• Chemical Name: 4,4-Difluorocyclohexane-1-carbonyl chloride
• CAS No.: 376348-75-3
• Molecular Formula: C7H9ClF2O
• Molecular Weight: 182.598
• Hs Code.: 2916200090
• DSSTox Substance ID: DTXSID40595985
• Wikidata: Q82491107
• Mol file: 376348-75-3.mol

Synonyms:376348-75-3;4,4-difluorocyclohexane-1-carbonyl chloride;4,4-Difluorocyclohexanecarbonyl chloride;Cyclohexanecarbonyl chloride, 4,4-difluoro- (9CI);MFCD13173983;4,4-difluorocyclohexane-1-carbonylchloride;4,4-DIFLUORO-CYCLOHEXANECARBONYL CHLORIDE;SCHEMBL167272;DTXSID40595985;AC8973;AKOS017514991;BS-52474;SY253184;DB-294904;EN300-142276;4,4-difluorocyclohexane carboxylic acid chloride

Chemical Property of 4,4-Difluorocyclohexane-1-carbonyl chloride

Chemical Property:

• Vapor Pressure: 0.702mmHg at 25°C
• Boiling Point: 185.311°C at 760 mmHg
• Flash Point: 65.874°C
• PSA: 17.07000
• Density: 1.25g/cm³
• LogP: 2.57730
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 182.0309989
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

4,4-Difluorocyclohexanecarbonylchloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CCC1C(=O)Cl)(F)F

Technology Process of 4,4-Difluorocyclohexane-1-carbonyl chloride

There total 5 articles about 4,4-Difluorocyclohexane-1-carbonyl chloride 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: 100.0%

4,4-difluorocyclohexanecarboxylic acid (122665-97-8) → 4,4-difluorocyclohexane-1-carbonyl chloride (376348-75-3)

Guidance literature:

With thionyl chloride; In toluene; at 92 ℃; for 2.5h; Inert atmosphere; Large scale;

DOI:10.1021/op8000614

Reference yield:

ethyl 4,4-difluorocyclohexane-1-carboxylate (178312-47-5) → 4,4-difluorocyclohexane-1-carbonyl chloride (376348-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water; methanol / 15 h / 20 °C / Inert atmosphere

2: thionyl chloride / toluene / 2.5 h / 92 °C / Inert atmosphere; Large scale

With thionyl chloride; sodium hydroxide; In methanol; water; toluene;

DOI:10.1021/op8000614

Reference yield:

ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4) → 4,4-difluorocyclohexane-1-carbonyl chloride (376348-75-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diethylamino-sulfur trifluoride / dichloromethane / 0 - 20 °C / Inert atmosphere

1.2: 20 h / Inert atmosphere

2.1: sodium hydroxide / water; methanol / 15 h / 20 °C / Inert atmosphere

3.1: thionyl chloride / toluene / 2.5 h / 92 °C / Inert atmosphere; Large scale

With thionyl chloride; diethylamino-sulfur trifluoride; sodium hydroxide; In methanol; dichloromethane; water; toluene;

DOI:10.1021/op8000614

upstream raw materials:

4,4-difluorocyclohexanecarboxylic acid

thionyl chloride

ethyl 4-oxocyclohexane-1-carboxylate

ethyl 4,4-difluorocyclohexane-1-carboxylate

Downstream raw materials:

maraviroc

N-hydroxy(4,4-bisfluorocyclohexan)carboxamide

4,4-difluoro-N-((S)-3-((1R,3R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)-1-(naphthalen-2-yl)propyl)cyclohexanecarboxamide

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

Refernces

• 1、 Zhang, Peng,Zeng, Jia,Pan, Ping,Zhang, Xue-Jing,Yan, Ming. "Palladium-Catalyzed Migratory Insertion of Carbenes and C-C Cleavage of Cycloalkanecarboxamides". supporting information. p. 536 - 541. Retrieved 2022/01/20.
• 2、 Wei, Dian,Liu, Tu-Ming,Zhou, Bo,Han, Bing. "Decarboxylative Borylation of mCPBA-Activated Aliphatic Acids". supporting information. p. 234 - 238. Retrieved 2020/01/02.