54856-20-1

Basic information

• Product Name: Benzoic acid, 2-[(3-oxo-1,2-benzisothiazol-2(3H)-yl)thio]-, methyl ester
• CAS NO: 54856-20-1
• Molecular Formula: C15H11NO3S2
• Molecular Weight: 317.389
• Mol File: 54856-20-1.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 2-[(3-oxo-1,2-benzisothiazol-2(3H)-yl)thio]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-[(3-oxo-1,2-benzisothiazol-2(3H)-yl)thio]-, methyl ester(54856-20-1)
• EPA Substance Registry System: Benzoic acid, 2-[(3-oxo-1,2-benzisothiazol-2(3H)-yl)thio]-, methyl ester(54856-20-1)

Safety Data

• Hazardous Substances Data: 54856-20-1(Hazardous Substances Data)

Upstream product

• 4892-02-8 Methyl thiosalicylate 
• 5697-20-1 2-mercaptobenzamide 
• 94266-24-7 2-methoxycarbonylbenzenesulfenamide 
• 51-17-2 benzoimidazole 
• 2634-33-5 1,2-benzisothiazolin-3-one 
• 67-56-1 methanol 

Downstream Products

• 2634-33-5 1,2-benzisothiazolin-3-one 
• 55255-10-2 methyl 2-[N-(p-chlorophenyl)sulfenamoyl]benzoate 
• 4299-09-6 2-(2-hydroxyethyl)-1,2-benzisothiazol-3(2H)-one 
• 2514-33-2 2-(4-methoxyphenyl)-1,2-benzisothiazol-3-one 
• 2514-30-9 2-(4-tolyl)-1,2-benzisothiazol-3-one 
• 2527-03-9 2-phenyl-1,2-benzisothiazolin-3-one 
• 67373-13-1 2-phenylsulfanyl-benzoic acid methyl ester 
• 2514-36-5 2-benzylbenzo[d]isothiazol-3(2H)-one 
• 34757-96-5 N-benzyl-2-(methoxycarbonyl)benzenesulfenamide 

Relevant articles and documents

The synthesis and reaction of N-sulfenyl heterocycles: Development of effective sulfenylating reagents

Various N-sulfenyl heterocycles were synthesized by transamination of sulfenamides using a chlorine gas-free method. The N-sulfenyl heterocycles behaved as sulfenylating reagents of anilines; N-sulfenylbenzimidazoles were the most effective.

Synthesis of 1,2-benzisothiazolin-3-one by transamination of sulfenamides

N-Substituted sulfenamoylbenzoates were synthesized by transamination of N-unsubstituted sulfenamoylbenzoates with amines. The reaction did not always proceed by simple amine exchange between the amines and ammonia on the sulfur atom of the sulfenamides. In reactions with aliphatic amines, the sulfenamides cyclized to form N-substituted 1,2-benzisothiazolin-3-ones. The synthesis of 1,2-benzisothiazolin-3-ones by intramolecular transamination was also investigated by S-amination of 2-mercaptobenzamides.

A facile synthesis of 1,2-benzisothiazolin-3-ones from thiosalicylates

Synthesis of 1,2-benzisothiazolin-3-ones by cyclization of 2- sulfenamoylbenzoates, which were prepared from amination of thiosalicylates by hydroxylamine-O-sulfonic acid, was examined. Although treatment of methyl 2-sulfenamoylbenzoate on heating gave unexpected 2-(2- methoxycarbonylphenylthio)-1,2-benzisothiazolin-3-one, the treatment with base at room temperature afforded 1,2-benzisothiazolin-3-one in a good yield.