20168-72-3

Basic information

• Product Name: Disulfide, 4-nitrophenyl phenyl
• CAS NO: 20168-72-3
• Molecular Formula: C12H9NO2S2
• Molecular Weight: 263.341
• Mol File: 20168-72-3.mol

Chemical Properties

• CAS DataBase Reference: Disulfide, 4-nitrophenyl phenyl(CAS DataBase Reference)
• NIST Chemistry Reference: Disulfide, 4-nitrophenyl phenyl(20168-72-3)
• EPA Substance Registry System: Disulfide, 4-nitrophenyl phenyl(20168-72-3)

Safety Data

• Hazardous Substances Data: 20168-72-3(Hazardous Substances Data)

Upstream product

• 937-32-6 4-nitrobenzenesulfenyl chloride 
• 108-98-5 thiophenol 
• 36744-95-3 S-p-nitrophenyl-S-phenylsulfilimine 
• 24698-06-4 S-p-nitrophenyl-S-phenyl-N-tosylsulfilimine 
• 28833-58-1 C₂₄H₂₀N₂O₄S₄ 
• 13113-79-6 sodium 4-nitrobenzenethiolate 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 882-33-7 diphenyldisulfane 
• 24067-17-2 4-nitrophenylboronic acid 
• 98-80-6 phenylboronic acid 
• 1849-36-1 para-nitrobenzenethiol 
• 14204-27-4 N-phenylthiophthalimide 
• 88683-47-0 2-((4-nitrophenyl)thio)isoindoline-1,3-dione 
• 1068439-08-6 [(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]benzene 

Downstream Products

• 20834-66-6 (2,4-dinitro-phenyl)-(4-nitro-phenyl)-sulfide 

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.

Transformation of arylboronic acids with sodium thiosulfate into organodisulfides catalyzed by a recyclable polyoxometalate-based Cr(iii) catalyst

Organo disulfides represent an abundant class of compounds in chemical biology, pharmaceutical fields, and industry. They are traditionally synthesized by the oxidation of mercaptan in the presence of an organic ligand supported metal catalyst or toxic oxidants under harsh conditions. Here, we disclose a highly-efficient pathway in which disulfide is synthesized by organic boric acid and Na2S2O3 using the catalyst (NH4)3[CrMo6O18(OH)6], demonstrating a high activity and excellent selectivity. Various boric acid derivatives have been successfully transformed into the corresponding disulfides. Mechanistic insights have been furnished based on the observation of intermediate and control experiments.

Fenton-Inspired C-H Functionalization: Peroxide-Directed C-H Thioetherification

Substoichiometric iron mediates the thioetherification of unactivated aliphatic C-H bonds directed by resident silylperoxides. Upon exposure to a catalytic amount of iron(II) triflate, TIPS-protected peroxides bearing primary, secondary, and tertiary C-H sites undergo chemoselective thioetherification of remote C-H bonds with diaryl disulfides. The reaction demonstrates a broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic experiments suggest that the reaction proceeds through 1,5-H atom abstraction by a hydroxyl radical generated with iron.

Unsymmetrical Disulfides Synthesis via Sulfenium Ion

An umpolung approach for the synthesis of unsymmetrical disulfides via sulfenium ion is reported. In situ generated electrophilic sulfenium ion from electron-rich thiols reacted with second thiols to yield unsymmetrical disulfides. Using an iodine catalyst and 4-dimethylaminopyridine (DMAP)/water as promoter, the target syntheses were achieved in one pot under aerobic condition.

Microwave-assisted synthesis of disulfides

A new microwave-assisted synthesis methodology for the preparation of substituted disulfide derivatives is presented. 4-Substituted sulfenimides were reacted with 4-substituted thiols under neat (to right doughy consistency) conditions in chloroform, with both microwave heating and conventional methods. The resulting 4-substituted disulfide derivatives were obtained at higher yields and in shorter reaction times with microwave heating. Their chemistry was confirmed by 1H-NMR, 13C-NMR, infrared (IR), and elemental analysis.

A versatile and convenient preparation of unsymmetrical diaryl disulfides

We have developed a convenient method for the synthesis of unsymmetrical diaryl disulfides under mild conditions in excellent yields. The described method is based on the straightforward preparation of 5,5-dimethyl-2-thioxo-1,3, 2-dioxaphosphorinane-2-sulfenyl bromide from readily available 5,5-dimethyl-2-sulfanyl-2-thioxo-l,3,2-dioxaphosphorinane or bis(5,5-dimethyl-2-thioxo-l,3,2-dioxaphosphorinan-2-yl) disulfide. The unsymmetrical diaryl disulfides can be obtained from aromatic thiol derivatives bearing electron-withdrawing or electron-donating groups. Thieme Stuttgart.

N-trifluoroacetyl arenesulfenamides, effective precursors for synthesis of unsymmetrical disulfides and sulfenamides

N-Trifluoroacetyl arenesulfenamides (3) were effective precursors for the synthesis of unsymmetrical disulfides (4) and sulfenamides (5). Reactions of 3 with a variety of aromatic thiols at room temperature were generally complete within 5 min and gave unsymmetrical diaryl disulfides in high yields. Aralkyl disulfides were isolated in high yields from the reaction of 3 with aliphatic thiols. The nucleophilic substitution reactions of 3 with amines proceeded smoothly and provided N-substituted sulfenamides in good to excellent yields.

Imination of sulfur-containing compounds: XXXV. New preparation method and oxidative benzenesulfonylimination of unsymmetrical disulfides

A new preparative method of synthesis was developed for unsymmetrical and symmetrical disulfides. This method involves sulfenylation of sodium thiolates with N-arenesulfenyl-N,N′-bis(arenesulfonyl)sulfinamidines. Imination of unsymmetrical disulfides with sodium chloroamides of sulfonic acids occurs at the more nucleophilic sulfur atom, affording N,N′ -bis(arenesulfonyl)sulfinamidines and symmetrical disulfides.

SULFENAMIDES AND SULFINAMIDES X OXIDATION OF THIOLS BY ARYL SULFINAMIDES

A dissection has been made of the oxidation of thiols by aryl sulfinamides, with the process explained by initial protonation of the sulfinyl group followed by a series of nucleophilic displacements, the first of which gives thiosulfinate and elimination of amine.The more usual reaction with thiosulfinate then gives disulfide, and sulfenic acid as a transitory intermediate, which by reaction with a third mole of thiol yields more disulfide.Reactions with lesser amounts of thiol permitted identification of intermediates.The effect of activation of the thiol isdiscussed.In contrast with oxidations by simpler sulfoxides the reaction proceeds without acid catalysis at ambient temperature, confirming the susceptibility to fission of the S-N bond in polar reactions.Key words: Sulfinamide, sulfenamide, thiol, fission, nucleophilic displacement, disulfide.

Ortho Effects in Organic Molecules on Electron Impact: 21 - Oxygen Transfers from the Ortho Nitro Group to Sulphur in N-Aryl-2-nitrobenzenesulphenamides and Phenyl-2-nitrophenyl Disulphide

Fragment ions arising as a result of oxygen transfer from the nito group to sulphur have been noticed in N-aryl-2-nitrobenzenesulphenamides and phenyl-2-nitrophenyl disulphide.In the case of the former a double oxygen transfer to the sulphur has been noti