63296-21-9

Basic information

• Product Name: Disulfide, methyl 4-nitrophenyl
• CAS NO: 63296-21-9
• Molecular Formula: C7H7NO2S2
• Molecular Weight: 201.27
• Mol File: 63296-21-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Disulfide, methyl 4-nitrophenyl(CAS DataBase Reference)
• NIST Chemistry Reference: Disulfide, methyl 4-nitrophenyl(63296-21-9)
• EPA Substance Registry System: Disulfide, methyl 4-nitrophenyl(63296-21-9)

Safety Data

• Hazardous Substances Data: 63296-21-9(Hazardous Substances Data)

Upstream product

• 118209-14-6 4-nitrophenyl disulphide anion 
• 74-88-4 methyl iodide 
• 45797-13-5 4-nitrophenylthiolate 
• 624-92-0 Dimethyldisulphide 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 2637-34-5 2-Sulfanylpyridine 
• 6320-03-2 2-chlorothiphenol 
• 2949-92-0 methanethiosulfonic acid S-methyl ester 
• 2043-76-7 S-ethyl methanethiosulfonate 
• 32846-80-3 S-isopropyl methanethiosulfonate 
• 24387-69-7 S-propyl methanethiosulfonate 
• 52017-46-6 S-butyl methanethiosulfonate 
• 18800-53-8 3,4-dimethylthiophenol 
• 4521-31-7 o-hydroxymethyl thiophenol 

Downstream Products

• 2080-82-2 S-p-nitrophenyl methanethiosulfonate 
• 17046-97-8 S-(4-nitrophenyl) 4-methylbenzenesulfonothioate 

Relevant articles and documents

NFSI-catalyzed S[sbnd]S bond exchange reaction for the synthesis of unsymmetrical disulfides

The metal-free S[sbnd]S bond exchange reaction of symmetrical disulfides catalyzed by NFSI is described. This novel protocol provides a facile and efficient approach to accessing important unsymmetrical disulfides. Furthermore, this strategy could also be utilized in the late-stage functionalization of amino acids, drugs, and natural products. The broad substrate scope, good functional group tolerance and easy accessibility of catalyst indicate that this strategy affords a green and practical complementary method to various unsymmetrical disulfides.

Unsymmetric aryl-alkyl disulfide growth inhibitors of methicillin-resistant Staphylococcus aureus and Bacillus anthracis

This study describes the antibacterial properties of synthetically produced mixed aryl-alkyl disulfide compounds as a means to control the growth of Staphylococcus aureus and Bacillus anthracis. Some of these compounds exerted strong in vitro bioactivity. Our results indicate that among the 12 different aryl substituents examined, nitrophenyl derivatives provide the strongest antibiotic activities. This may be the result of electronic activation of the arylthio moiety as a leaving group for nucleophilic attack on the disulfide bond. Small alkyl residues on the other sulfur provide the best activity as well, which for different bacteria appears to be somewhat dependent on the nature of the alkyl moiety. The mechanism of action of these lipophilic disulfides is likely similar to that of previously reported N-thiolated β-lactams, which have been shown to produce alkyl-CoA disulfides through a thiol-disulfide exchange within the cytoplasm, ultimately inhibiting type II fatty acid synthesis. However, the mixed alkyl-CoA disulfides themselves show no antibacterial activity, presumably due to the inability of the highly polar compounds to cross the bacterial cell membrane. These structurally simple disulfides have been found to inhibit β-ketoacyl-acyl carrier protein synthase III, or FabH, a key enzyme in type II fatty acid biosynthesis, and thus may serve as new leads to the development of effective antibacterials for MRSA and anthrax infections.

New and more potent antifungal bisulfides

From a design principle described in an earlier paper, a new series of substituted aryl methyl disulfides have been prepared and tested against Aspergillus niger and Aspergillus flavus. Methyl p-nitrophenyl disulfide is more potent (by an order of magnitude) than the fungitoxic natural product (CH3SCH2S)2. With the present rationale in hand, one can anticipate which Polycarpamine is an effective antifungal agent. CSIRO 2000.