Bis(4-nitrophenyl) disulfide

Base Information

• Chemical Name: Bis(4-nitrophenyl) disulfide
• CAS No.: 100-32-3
• Molecular Formula: C12H8N2O4S2
• Molecular Weight: 308.339
• Hs Code.: 29309090
• European Community (EC) Number: 202-840-5
• NSC Number: 677446,4566
• UNII: F16G70DEUU
• DSSTox Substance ID: DTXSID8059211
• Nikkaji Number: J4.004E
• Wikidata: Q27277502
• ChEMBL ID: CHEMBL333963
• Mol file: 100-32-3.mol

Synonyms:4,4'-dinitrodiphenyldisulfide;p-nitrophenyl disulfide

Chemical Property of Bis(4-nitrophenyl) disulfide

Chemical Property:

• Appearance/Colour: yellow or tan powder
• Melting Point: 141 °C
• Refractive Index: 1.6510 (estimate)
• Boiling Point: 478.783 °C at 760 mmHg
• Flash Point: 243.359 °C
• PSA: 142.24000
• Density: 1.528 g/cm³
• LogP: 5.34880
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 307.99254909
• Heavy Atom Count: 20
• Complexity: 308

Purity/Quality:

Bis(4-nitrophenyl) Disulfide >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-40
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])SSC2=CC=C(C=C2)[N+](=O)[O-]
• Uses: Reactant or reagent involved in:? ;Electrophilic cyclization of 2-alkynylanisoles1 or alkynylanilines2? ;Oxidative chlorination to sulfonyl chlorides3? ;Arylation with triarylbismuthanes4? ;Decarboxylative cross-coupling with dialkoxybenzoic acids5? ;Disulfidation of alkenes6 Reactant or reagent involved in:Electrophilic cyclization of 2-alkynylanisoles or alkynylanilinesOxidative chlorination to sulfonyl chloridesArylation with triarylbismuthanesDecarboxylative cross-coupling with dialkoxybenzoic acidsDisulfidation of alkenes

Technology Process of Bis(4-nitrophenyl) disulfide

There total 189 articles about Bis(4-nitrophenyl) disulfide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

4-Nitrobenzenesulfonyl chloride (98-74-8) → di(p-nitrophenyl) disulfide (100-32-3)

Guidance literature:

With ziconium(IV) oxychloride octahydrate; sodium iodide; In water; at 90 ℃; for 0.25h;

DOI:10.1080/10426507.2010.519159

Reference yield: 90.0%

4-nitrobenzenesulfenyl chloride (937-32-6) → di(p-nitrophenyl) disulfide (100-32-3)

Guidance literature:

With triphenylphosphine; In acetonitrile; for 2h; Ambient temperature;

Reference yield: 65.0%

4-nitro-4’-chlorodiphenylsulfoxide (24535-53-3) → 4,4'-dichlorodiphenyl disulfide (1142-19-4) + di(p-nitrophenyl) disulfide (100-32-3) + p-chlorobenzenesulphinamide (16096-86-9)

Guidance literature:

With sulfur; ammonia; at 20 ℃; for 6h;

DOI:10.1246/cl.1983.535

upstream raw materials:

piperidine

4-nitrophenyl thiocyanate

pyridine

4-chloropyridine N-oxide

Downstream raw materials:

2-methyl-6-(4-nitro-phenylsulfanyl)-2,3-dihydro-[1,4]dithiino[2,3-c]pyrrole-5,7-dione

6-(4-nitro-phenylsulfanyl)-2-phenyl-2,3-dihydro-[1,4]dithiino[2,3-c]pyrrole-5,7-dione

N-Acetyl-p-nitrobenzenesulfenamide

N_.N'-Bis(p-tosyl)-p-nitrobenzolsulfinamidin

Refernces

• 1、 Rybakova, I. A.,Shekhtman, R. I.,Prilezhaeva, E. N.,Litvinov, V. P.,Shakhovskoi, G. P.. "REDUCTION OF HALONITROBENZENES TO HALOANILINES BY HYDROGEN SULFIDE". . p. 1901 - 1903. Retrieved 1991.
• 2、 Sainte-Marie, Laurent,Guibe-Jampel, Eryka,Therisod, Michel. "Facile solvent-free oxidation of thiols mediated by mineral supports". . p. 9661 - 9662. Retrieved 1998.
• 3、 Hirano, Masao,Yakabe, Sigetaka,Monobe, Hiroyuki,Morimoto, Takashi. "Alumina: An Efficient and Reusable Catalyst for the Oxidative Coupling of Thiols with DMSO". . p. 472 - 473. Retrieved 1998.
• 4、 Nowrouzi, Najmeh,Abbasi, Mohammad,Latifi, Hadis. "Ligand-free copper-catalysed direct synthesis of diaryl sulfides and diaryl disulfides in wet poly(ethylene glycol)". . . Retrieved 2017.
• 5、 Al-Khalil,Bowman,Gaitonde,Marley,Richardson. "Radical-nucleophilic substitution (SRN1) reactions. Part 7. Reactions of aliphatic α-substituted nitro compounds". . p. 1557 - 1565. Retrieved 2001.
• 6、 Soleiman-Beigi, Mohammad,Mohammadi, Fariba. "A novel nickel-catalyzed domino method for the direct synthesis of symmetrical disulfides using potassium 5-methyl-1,3,4-oxadiazole-2-thiolate as a sulfurating reagent". . p. 911 - 914. Retrieved 2015.
• 7、 Cornelis, Andre,Depaye, Nicole,Gerstmans, Andre,Laszlo, Pierre. "CLAY-SUPPORTED REAGENTS IV. A NOVEL COUPLING OF THIOLS INTO DISULPHIDES, VIA THIONITRITE INTERMEDIATES USING A CLAY-SUPPORTED NITROSATION REAGENT.". . p. 3103 - 3106. Retrieved 1983.
• 8、 Soleiman-Beigi, Mohammad,Arzehgar, Zeinab. "Ni-Catalyzed Cross-Coupling Reaction: The Direct Synthesis of Symmetrical Disulfanes from Aryl and Primary Alkyl Halides". . p. 355 - 360. Retrieved 2015.
• 9、 Hodson,Holt. "-". . p. 1602. Retrieved 1968.
• 10、 Hoggarth,Sexton. "-". . p. 815,816. Retrieved 1947.