599-89-3

Basic information

• Product Name: 4-chlorophenyl 4-methylbenzenesulfonate
• Synonyms: 4-chlorophenyl 4-methylbenzenesulfonate;4-Chlorophenyl p-toluenesulfonate;p-Toluenesulfonic acid 4-chlorophenyl ester
• CAS NO: 599-89-3
• Molecular Formula: C₁₃H₁₁ClO₃S
• Molecular Weight: 282.74264
• Mol File: 599-89-3.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 415.6°Cat760mmHg
• Flash Point: 205.2°C
• Appearance: /
• Density: 1.337g/cm³
• Vapor Pressure: 9.8E-07mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: 4-chlorophenyl 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chlorophenyl 4-methylbenzenesulfonate(599-89-3)
• EPA Substance Registry System: 4-chlorophenyl 4-methylbenzenesulfonate(599-89-3)

Safety Data

• Hazardous Substances Data: 599-89-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H11ClO3S/c1-10-2-8-13(9-3-10)18(15,16)17-12-6-4-11(14)5-7-12/h2-9H,1H3

Upstream product

• 106-48-9 4-chloro-phenol 
• 98-59-9 p-toluenesulfonyl chloride 
• 104-15-4 toluene-4-sulfonic acid 
• 1017246-80-8 10-(4-chlorophenyl)phenothiabismine 5,5-dioxide 
• 1245716-47-5 ethyl 4-methyl-6-phenyl-2-(tosyloxy)pyrimidine-5-carboxylate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 1950-78-3 p-toluenesulfonyl iodide 

Downstream Products

• 613-37-6 4-methoxylbiphenyl 
• 636-09-9 diethyl terephthalate 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 4703-22-4 N-tosylpiperidine 
• 106-48-9 4-chloro-phenol 
• 10504-98-0 N-(4-chlorobenzyl)-p-toluenesulfonamide 
• 13159-74-5 4-chloro-N-(4-chlorobenzyl)aniline 
• 104-15-4 toluene-4-sulfonic acid 
• 54879-64-0 N-[(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide 
• 104329-18-2 N-(4-chlorophenyl)-4-methoxybenzenemethanamine 
• 2948-37-0 N-(4-chlorophenyl)benzylamine 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 10504-92-4 N-p-xylyl-p-toluenesulfonamide 
• 73842-46-3 N-[(4-methylphenyl)methyl]-4-chloroaniline 

Relevant articles and documents

Electrochemical cross-coupling reactions of sodium arenesulfinates with thiophenols and phenols

A green electrochemical oxidative cross-coupling protocol for the generation of thiosulfonates and sulfonate esters using sodium arenesulfinates and thiophenols/phenols is disclosed. The protocol involves using inorganic and non-toxic NaI as both redox catalyst and supporting electrolyte at room temperature without oxidant and base. The reactions provide good yields of products and tolerate broad substrate scope. The mechanistic studies revealed that the reactions proceed via a radical pathway for the formation of SO2–S and SO2–O bonds.

The Synthesis and Catalytic Activity of New Mixed NHC-Phosphite Nickel(0) Complexes

Herein we describe the synthesis and isolation of the first low-valent NHC-phosphite nickel complexes of general formula Ni(NHC)[P(OAr)3]2. These three-coordinate Ni(0) compounds were fully characterized, including by X-ray crystallography that highlighted their trigonal planar geometry. The representative complex Ni(IMes)[P(OPh)3]2 was used to show that a phosphite ligand is readily substituted in the presence of an aldehyde or nitrile. These stoichiometric studies then led to an investigation of their catalytic properties in the Suzuki-Miyaura cross-coupling reactions between aryl tosylates and aryl boronic acids, a first for such a NHC-Ni catalyst. Finally, mechanistic investigations led to the isolation of a well-defined oxidative addition product.

LiCl-Accelerated Nickel Catalyzed Cross-Coupling of Aryl Tosylates with the Aryl Grignard Reagents

A mild coupling reaction catalyzed by Ni(acac)2-L4 has been studied. The catalyst acts efficiently in the reaction of biaryl coupling between various electrophiles and common or functionalized aryl Grignard reagents with high functional group tolerance. The study demonstrates that LiCl acts as an essential component in efficient cross-coupling by accelerating reduction of Ni(II) to Ni(0). The new catalytic system for selective couplings of aryl tosylates with aryl chlorides has been developed.