Diphenyl disulfide

Base Information

• Chemical Name: Diphenyl disulfide
• CAS No.: 882-33-7
• Deprecated CAS: 1071709-24-4,1195339-75-3,1195339-75-3
• Molecular Formula: C12H10S2
• Molecular Weight: 218.343
• Hs Code.: 29093090
• European Community (EC) Number: 212-926-4
• NSC Number: 2689
• UNII: 7P54H519IJ
• DSSTox Substance ID: DTXSID6022131
• Nikkaji Number: J2.117B
• Wikipedia: Diphenyl_disulfide
• Wikidata: Q2423101
• Metabolomics Workbench ID: 45132
• ChEMBL ID: CHEMBL462861
• Mol file: 882-33-7.mol

Synonyms:diphenyl disulfide

Chemical Property of Diphenyl disulfide

Chemical Property:

• Appearance/Colour: White to light yellow crystal
• Vapor Pressure: 0.00113mmHg at 25°C
• Melting Point: 58-60 °C
• Refractive Index: 1,441-1,444
• Boiling Point: 310 °C at 760 mmHg
• Flash Point: 177.8 °C
• PSA: 50.60000
• Density: 1.22 g/cm³
• LogP: 4.48600
• Storage Temp.: Store below +30°C.
• Solubility.: xylene: soluble3%, clear, colorless to yellow
• Water Solubility.: Insoluble in water.
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 218.02239267
• Heavy Atom Count: 14
• Complexity: 128

Purity/Quality:

99%+ ^*data from raw suppliers

Diphenyl Disulfide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53
• Safety Statements: 26-37/39-36-61-60

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C1=CC=C(C=C1)SSC2=CC=CC=C2
• Description: Diphenyl disulfide is a colorless crystalline material with the formula (C6H5S)2 and often abbreviated Ph2S2. It is most commonly utilized as a reagent for integration of a phenylthio functionality into molecules. The phenylthio group in the compound has a useful function due to the numerous of reaction that it can facilitate in organic chemistry. Phenysulfides, for instance, undergo oxidative elimination, producing alkenes under relatively mild, normal conditions. Also phenyl sulfides can serve as a source of carbon-centered radicals in radical reactions. Diphenyl disulfide is usually synthesized by the oxidation of thiophenol: 2 PhSH + I2 → Ph2S2 + 2 HI
• Uses: Diphenyl disulfide is one of the most popular organic disulfides used in organic synthesis. It is used as a reagent for the α-phenylsulfenylation of carbonyl compounds. It participates in hydrothiolation of alkynes via amine-mediated single electron transfer mechanism. It is the hydrolysis product of dyfonate.

Technology Process of Diphenyl disulfide

There total 2010 articles about Diphenyl 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: 98.0%

α-naphthol (90-15-3) + 4'-nitrobenzenesulfenanilide (64168-52-1) → 2-phenylthio-1-naphthol (68143-73-7) + 4-(phenylthio)naphthalen-1-ol (19133-53-0) + 4-nitro-aniline (100-01-6,104810-17-5) + diphenyldisulfane (882-33-7)

Guidance literature:

With trifluoroacetic acid; In benzene; for 0.166667h; Further byproducts given; Ambient temperature;

Reference yield: 98.0%

4'-nitrobenzenesulfenanilide (64168-52-1) → S-Phenyl benzenethiosulfonate (1212-08-4) + 4-nitro-aniline (100-01-6,104810-17-5) + diphenyldisulfane (882-33-7)

Guidance literature:

With trifluoroacetic acid; In benzene; at 25 ℃; Product distribution; Mechanism; further sulfenanilide;

Reference yield: 79.0%

furan (110-00-9) + N-methyl-4-nitro-N-(phenylthio)benzenamine (110228-59-6) → 2-phenylthiofuran (16003-14-8) + N-methyl-2-(phenylthio)-4-nitroaniline (110228-60-9) + N-methyl(p-nitroaniline) (100-15-2) + diphenyldisulfane (882-33-7)

Guidance literature:

at 85 ℃; for 144h;

upstream raw materials:

1,4-dioxane

(2-chloro-phenyl)-phenyl disulfide

1-(4-methoxyphenyl)-2-phenyldisulfane

pyridine

Downstream raw materials:

phenylsulfanyl-succinic acid

Benzyl phenyl sulfide

diphenyl sulfide

(1-phenylethane-1,2-diyl)bis(phenylsulfane)

Refernces

• 1、 Koizumi, Toshio,Bashir, Nadeem,Murphy, John A.. "Reactions of arenediazonium salts with diazadithiafulvalenes". . p. 7635 - 7638. Retrieved 1997.
• 2、 Tanaka, Hideo,Ogawa, Hidenori,Suga, Hiroaki,Torii, Sigeru,Jutand, Anny,Aziz, Said,Suarez, Alejandra G.,Amatore, Christian. "Electrogeneration of triphenyltin radical, anion, and cation. Electrochemical initiation of tin hydride-promoted radical chain reactions". . p. 9402 - 9408. Retrieved 1996.
• 3、 Bragina, I. O.,Kandror, I. I.. "RADICAL PHENYLATION OF AMIDES OF THIOCINNAMIC ACID". . p. 610 - 612. Retrieved 1983.
• 4、 Tsuda et al.. "-". . p. 1517,1518. Retrieved 1965.
• 5、 Wang, Junlei,Huang, Binbin,Yang, Chao,Xia, Wujiong. "Visible-light-mediated defluorinative cross-coupling of: Gem-difluoroalkenes with thiols". . p. 11103 - 11106. Retrieved 2019.
• 6、 Leong, Paul,Lautens, Mark. "Rhodium-Catalyzed Asymmetric Ring Opening of Oxabicyclic Alkenes with Sulfur Nucleophiles". . p. 2194 - 2196. Retrieved 2004.
• 7、 Burasov, Alexander V.,Paddon, Christopher A.,Bhatti, Earrah L.,Donohoe, Timothy J.,Compton, Richard G.. "Cryoelectrochemical reduction of a phenyl sulfide in tetrahydrofuran: Mediated reduction gives different products compared to direct reduction". . p. 144 - 150. Retrieved 2007.
• 8、 Kanatzidis, Mercouri G.. "-". . p. 101 - 104. Retrieved 1990.
• 9、 Marti, Vicente,Fernandez, Lorenzo,Fornes, Vicente,Garcia, Hermenegildo,Roth, Heinz D.. "UV-vis and IR spectroscopic characterization of diphenyl disulfide radical cation in acid zeolites and its rearrangement to thianthrenium radical cation". . p. 145 - 152. Retrieved 1999.
• 10、 Jones, Ray,Morris, Janet L.,Rees, Charles W.,Williams, David J.. "Tetrathiatetraza-azulene; Synthesis and X-Ray Crystal Structure". . p. 1654 - 1656. Retrieved 1985.