64826-51-3

Basic information

• Product Name: Pyridine, 2-(phenyldithio)-, 1-oxide
• CAS NO: 64826-51-3
• Molecular Formula: C11H9NOS2
• Molecular Weight: 235.331
• Mol File: 64826-51-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Pyridine, 2-(phenyldithio)-, 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 2-(phenyldithio)-, 1-oxide(64826-51-3)
• EPA Substance Registry System: Pyridine, 2-(phenyldithio)-, 1-oxide(64826-51-3)

Safety Data

• Hazardous Substances Data: 64826-51-3(Hazardous Substances Data)

Upstream product

• 180253-99-0 (Methyl-phenylsulfanyl-amino)-acetic acid ethyl ester 
• 180253-94-5 2-tert-Butoxycarbonylamino-2-methyl-propionic acid 2-thioxo-2H-pyridin-1-yl ester 
• 180253-97-8 2-Benzyloxycarbonylamino-2-methyl-propionic acid 2-thioxo-2H-pyridin-1-yl ester 
• 1121-31-9 2-mercaptopyridine N-oxide 
• 108-98-5 thiophenol 
• 931-59-9 benzenesulfenyl chloride 
• 3696-28-4 2,2'-dipyridyl disulfide bis-N-oxide 
• 180253-98-9 Phenylsulfanylamino-acetic acid ethyl ester 
• 19117-30-7 S-phenyl-N,N-diisopropyl-sulfenamide 
• 91233-19-1 1-(adamantane-1-carbonyloxy)pyridine-2(1H)-thione 
• 114050-31-6 3-Phenyl-propionic acid 2-thioxo-2H-pyridin-1-yl ester 
• 105398-69-4 Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester 
• 14933-91-6 N-phenyl-benzenesulphenamide 
• 104047-14-5 4-Nitro-benzoic acid 2-thioxo-2H-pyridin-1-yl ester 

Downstream Products

• 1121-30-8 1-hydroxy-2(1H)-pyridinethione 
• 20126-55-0 2-propyl-1-phenyldisulfane 
• 882-33-7 diphenyldisulfane 

Relevant articles and documents

New reactions of the thiocarbonyl function. The synthesis of hindered peptides

The well-known radical chemistry of the thiocarbonyl function has been expanded to include the concerted reaction between an O-acyl derivative of N-hydroxypyridine-2(1H)-thione (a Barton PTOC ester) and a sulfenamide. The atom-economical process spawned a carboxamide and an unsymmetrical disulfide of synthetic and biological value. The reaction was successfully applied to the synthesis of sterically encumbered, urethane-protected dipeptides. The oxidation-reduction technology pertaining to the disulfide-phosphine combination facilitated the generation of transient Barton PTOC esters. In conjunction with the appropriate benzenesulfenamide, the Barton PTOC ester of benzoyl-L-leucine was shown to preserve optical integrity according to the sensitive Young test, albeit at low temperature. However, the thermodynamic forces at play are powerful and, as a result, the yields were not compromised. In all but the sterically demanding instances, the parent free amine almost matched the reaction time, yield, and enantiomeric excess of the corresponding benzenesulfenamide in its reaction with a Barton PTOC ester.

N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters. Part I. The synthesis of carboxamides

The reaction between an acyl derivative of N-hydroxypyridine-2(1H)- thione (a Barton PTOC ester) and either an amine (primary or secondary), or the corresponding sulfenamide, led to the formation of a carboxamide in a clean transformation requiring minimal work-up and purification. The reaction with a sulfenamide is particularly useful since the only by-product, an unsymmetrical disulfide, is of both synthetic and biological value. In sterically demanding cases, Barton PTOC esters were more reactive towards benzenesulfenamides than to the corresponding free amines.

Unsymmetrical disulfides as antimicrobial agents

Novel unsymmetrical disulfides of pyridine-1-oxide and acid addition salts thereof, having particular utility as antimicrobial agents per se and in skin cleansing detergent compositions, shampoos, hair dressings, disinfectants, preservatives and the like.