N-Cyclohexyl 4-fluorobenzenesulfonamide

Base Information

• Chemical Name: N-Cyclohexyl 4-fluorobenzenesulfonamide
• CAS No.: 565-40-2
• Molecular Formula: C₁₂H₁₆FNO₂S
• Molecular Weight: 257.329
• DSSTox Substance ID: DTXSID70355392
• Wikidata: Q82134263
• Mol file: 565-40-2.mol

Synonyms:N-CYCLOHEXYL 4-FLUOROBENZENESULFONAMIDE;565-40-2;N-cyclohexyl-4-fluorobenzenesulfonamide;N-Cyclohexyl4-fluorobenzenesulfonamide;Oprea1_571586;Oprea1_657770;SCHEMBL14842346;DTXSID70355392;MFCD01213082;STK006961;AKOS000565682;SB81490;BS-23741;N-cyclohexyl-4-fluoro-1-benzenesulfonamide;N-cyclohexyl-4-fluorobenzene-1-sulfonamide;CS-0208458;A869913

Chemical Property of N-Cyclohexyl 4-fluorobenzenesulfonamide

Chemical Property:

• Boiling Point: 370.8±44.0 °C(Predicted)
• PKA: 11.72±0.20(Predicted)
• Density: 1.26±0.1 g/cm3(Predicted)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 257.08857809
• Heavy Atom Count: 17
• Complexity: 325

Purity/Quality:

98.5% ^*data from raw suppliers

N-Cyclohexyl4-fluorobenzenesulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC(CC1)NS(=O)(=O)C2=CC=C(C=C2)F

Technology Process of N-Cyclohexyl 4-fluorobenzenesulfonamide

There total 4 articles about N-Cyclohexyl 4-fluorobenzenesulfonamide 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: 88.0%

4-fluorophenylsulphonamide (402-46-0) + cyclohexene (110-83-8) → N-cyclohexyl-4-fluorobenzenesulfonamide (565-40-2)

Guidance literature:

With iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C₂₀]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; 2,4,6-Triisopropylthiophenol; tricyclohexylphosphine; at 20 ℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;

DOI:10.1021/jacs.1c09484

Reference yield: 87.7%

4-Fluorobenzenesulfonyl chloride (349-88-2) + cyclohexylamine (108-91-8,157973-60-9) → N-cyclohexyl-4-fluorobenzenesulfonamide (565-40-2)

Guidance literature:

With triethylamine; In dichloromethane; for 16h;

Reference yield: 67.0%

4-fluorophenylsulphonamide (402-46-0) + Cyclohexanecarboxylic acid (98-89-5) → N-cyclohexyl-4-fluorobenzenesulfonamide (565-40-2)

Guidance literature:

With copper(I) thiophene-2-carboxylate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(5-methyl-2-(4-fluorophenyl)pyridine(-1H))-iridium(III) hexafluorophosphate; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; bathophenanthroline; iodomesitylene diacetate; In 1,4-dioxane; at 20 ℃; for 1h; regioselective reaction; Inert atmosphere; Irradiation;

DOI:10.1038/s41586-018-0234-8

upstream raw materials:

4-Fluorobenzenesulfonyl chloride

cyclohexylamine

4-fluorophenylsulphonamide

Cyclohexanecarboxylic acid

Downstream raw materials:

4-((N-cyclohexyl-4-fluorophenylsulfonamido)methyl)benzoic acid

Refernces

• 1、 Laudadio, Gabriele,Barmpoutsis, Efstathios,Schotten, Christiane,Struik, Lisa,Govaerts, Sebastian,Browne, Duncan L.,No?l, Timothy. "Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols". supporting information. . Retrieved 2019/04/16.
• 2、 Liang, Yufan,Zhang, Xiaheng,MacMillan, David W. C.. "Decarboxylative sp 3 C-N coupling via dual copper and photoredox catalysis". . p. 83 - 88. Retrieved 2018/07/24.