2437-33-4

Basic information

• Product Name: phenyl 4-chlorobenzenesulfonate
• Synonyms: Benzenesulfonic acid, p-chloro-, phenyl ester
• CAS NO: 2437-33-4
• Molecular Formula: C₁₂H₉ClO₃S
• Molecular Weight: 268.7161
• Mol File: 2437-33-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 400°C at 760 mmHg
• Flash Point: 195.7°C
• Density: 1.377g/cm³
• Vapor Pressure: 3.04E-06mmHg at 25°C
• Refractive Index: 1.601
• CAS DataBase Reference: phenyl 4-chlorobenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 4-chlorobenzenesulfonate(2437-33-4)
• EPA Substance Registry System: phenyl 4-chlorobenzenesulfonate(2437-33-4)

Safety Data

• Hazardous Substances Data: 2437-33-4(Hazardous Substances Data)

Upstream product

• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 108-95-2 phenol 
• 92964-93-7 1-naphthalenesulfonic acid phenyl ester 
• 1286023-30-0 phenyl 4-trifluoromethylbenzenesulfonate 
• 42823-94-9 phenyl 4-cyanobenzenesulfonate 
• 98-66-8 4-chloro-benzenesulfonic acid 
• 622-46-8 carbamic acid phenyl ester 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 139-02-6 sodium phenoxide 

Downstream Products

• 758640-21-0 N-Benzylaniline 
• 98-66-8 4-chloro-benzenesulfonic acid 
• 10504-90-2 N-benzyl-4-chlorobenzenesulfonamide 
• 108-95-2 phenol 
• 116013-81-1 phenyl 4-ethylbenzenesulfonate 
• 80-33-1 chlorofensone 
• 6621-62-1 4-chloro-benzenesulfonic acid-(2,4-dichloro-phenyl ester) 
• 15818-64-1 N-(4-methylbenzyl)aniline 
• 10504-94-6 4-chloro-N-(4-methylbenzyl)benzenesulfonamide 
• 3526-43-0 N-(4-methoxybenzyl)aniline 
• 349397-05-3 4-chloro-N-(4-methoxybenzyl)benzenesulfonamide 
• 4750-61-2 N-(p-chlorobenzyl)aniline 

Relevant articles and documents

Practical Electro-Oxidative Sulfonylation of Phenols with Sodium Arenesulfinates Generating Arylsulfonate Esters

A practical and sustainable synthesis of arylsulfonate esters has been developed through electro-oxidation. This reaction employed the stable and readily available phenols and sodium arenesulfinates as the starting materials and took place under mild reaction conditions without additional oxidants. A wide range of arylsulfonate esters including those bearing functional groups were produced in good to excellent yields. This reaction could also be conducted at a gram scale without a decrease of reaction efficiency. Those results well demonstrated the potential synthetic value of this reaction in organic synthesis.

A new preparative method of aryl sulfonate esters by using cyclic organobismuth reagents

A new method for the preparation of aryl sulfonate esters by using a cyclic pentavalent bismuth is described. Aryl sulfonate esters are formed in good to high yields by treating 10-arylphenothiabismine 5,5-dioxides, m-chloroperoxybenzoicacid (m-CPBA)and various sulfonic acids in dichloromethane.

Competitive Reaction Pathways in the Nucleophilic Substitution Reactions of Aryl Benzenesulfonates with Benzylamines in Acetonitrile

The reactions of aryl benzenesulfonates (YC6H4SO2OC6H4Z) with benzylamines (XC6H4CH2NH2) in acetonitrile at 65.0 deg C have been studied. The reactons proceed competitevely by S-O (kS-O) and C-O (kC-O) bond scission, but the former provides the major reaction pathway. On the basis of analysis of the Hammet and Broensted coefficients together with the cross-interaction constants ρXY, ρYZ, and ρXZ, stepwise mechanisms are proposed in which the S-O bond cleavage proceeds by rate-limiting formation of a trigonal-bipyramidal pentacoordinate (TBP-5C) intermediate, whereas the C-O bond scission takes place by rate-limiting expulsion of the sulfonate anion (YC6H4SO3-) from a Meisenheimer-type complex.