p-TOLUENESULFONYL FLUORIDE

Base Information

• Chemical Name: p-TOLUENESULFONYL FLUORIDE
• CAS No.: 455-16-3
• Molecular Formula: C7H7 F O2 S
• Molecular Weight: 174.196
• Hs Code.: 29049095
• European Community (EC) Number: 207-238-6
• NSC Number: 2749
• DSSTox Substance ID: DTXSID0060014
• Nikkaji Number: J55H
• Wikidata: Q81989031
• Mol file: 455-16-3.mol

Synonyms:4-PMSF;4-toluenesulfonyl fluoride;alpha-tolylsulfonyl fluoride;p-toluenesulfonyl fluoride;para-toluenesulfonyl fluoride;phenylmethane sulfonyl fluoride;tosyl fluoride;TSF

Chemical Property of p-TOLUENESULFONYL FLUORIDE

Chemical Property:

• Appearance/Colour: White to beige fused mass
• Vapor Pressure: 0.0873mmHg at 25°C
• Melting Point: 41-42 °C(lit.)
• Boiling Point: 112 °C16 mm Hg(lit.)
• Flash Point: 87.2°C
• PSA: 42.52000
• Density: 1.276g/cm³
• LogP: 2.73400
• Sensitive.: Moisture Sensitive
• Water Solubility.: Hydrolyzes in water.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 174.01507880
• Heavy Atom Count: 11
• Complexity: 209

Purity/Quality:

98%,99%, ^*data from raw suppliers

p-Toluenesulfonyl fluoride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 22-26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)F
• Uses: p-Toluenesulfonyl fluoride is used for sulfonylation of organometallic reagents as a simple, one-step synthesis of sulfones. It is useful in the treatment of Alzheimer?s disease. It is used to study the DNS polymerase from spinach leaf extracts. It was used in isolation and separation of Pseudomonas aeruginosa membranes by density sucrose gradient centrifugation. Protease inhibitor.

Technology Process of p-TOLUENESULFONYL FLUORIDE

There total 39 articles about p-TOLUENESULFONYL FLUORIDE 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%

di(4-methyl)phenylthiosulfonate (2943-42-2) → p-toluenesulfonyl fluoride (455-16-3)

Guidance literature:

With Selectfluor; In water; acetonitrile; at 20 ℃; for 1.5h; Reflux;

DOI:10.1016/j.tet.2014.02.013

Reference yield: 100.0%

p-toluenesulfonyl chloride (98-59-9) → p-toluenesulfonyl fluoride (455-16-3)

Guidance literature:

With potassium hydrogen bifluoride; polyethylene glycol-1000; In water; acetone; at 50 ℃; for 1.75h; other alkali metal fluorides, other solvents, other temp., polyethylene glycols with different molecular weight;

Reference yield: 95.0%

silver(I) 4-methylbenzenesulfonate (16836-95-6) → p-toluenesulfonyl fluoride (455-16-3)

Guidance literature:

silver(I) 4-methylbenzenesulfonate; With 1,3,5-trichloro-2,4,6-triazine; tetrabutylammomium bromide; In acetonitrile; at 60 ℃; for 12h;

With potassium hydrogen difluoride; In acetone; acetonitrile; at 20 ℃; for 12h;

DOI:10.1039/c9ra02531f

upstream raw materials:

toluene-4-sulfonamide

p-toluenesulfonyl chloride

sodium 4-methylbenzenesulfinate

toluene-4-sulfonic acid

Downstream raw materials:

[(p-methylphenyl)sulfonylmethyl]isonitrile

α-tosylbenzyl isocyanide

α-Tosylaethyliden-triphenylphosphoran

methyl p-toluene sulfinate

Refernces

• 1、 Yadav, Ganapati D.,Paranjape, Priyanvada M.. "Novelties of solid-liquid phase transfer catalysed synthesis of p-toluenesulfonyl fluoride from p-toluenesulfonyl chloride". . p. 289 - 295. Retrieved 2005.
• 2、 Zhao, Shiyu,Guo, Yong,Su, Zhaoben,Wu, Chengying,Chen, Wei,Chen, Qing-Yun. "Deoxyfluorination of Carboxylic, Sulfonic, Phosphinic Acids and Phosphine Oxides by Perfluoroalkyl Ether Carboxylic Acids Featuring CF2O Units". supporting information. p. 1225 - 1232. Retrieved 2021/05/04.
• 3、 Bui, Tien Tan,Kim, Hee-Kwon,Tran, Van Hieu. "Visible-Light-Mediated Synthesis of Sulfonyl Fluorides from Arylazo Sulfones". . . Retrieved 2021/10/14.