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
• General Description: Diphenyl disulfide is an aromatic disulfide that participates in cobalt carbonyl-catalyzed reactions, undergoing carbonylation with carbon monoxide to form thioesters or desulfurization in the presence of t-butyl peroxide to yield sulfides. These transformations involve intermediate cobalt complexes and CO insertion, demonstrating its reactivity in organosulfur chemistry.

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:

Benzyl phenyl sulfide

diphenyl sulfide

S-phenyl α-chlorothioacetate

1-naphthyl phenyl sulfide

Refernces

COBALT CARBONYL CATALYZED REACTIONS OF DISULFIDES: CARBONYLATION TO THIOESTERS AND DESULFURIZATION TO SULFIDES.

10.1016/S0040-4039(00)98115-2

The research focused on the catalytic reactions of disulfides using cobalt carbonyl, aiming to investigate the desulfurization and carbonylation of organic sulfur compounds. The study concluded that aromatic and benzylic disulfides react with carbon monoxide and a catalytic amount of cobalt carbonyl to produce thioesters and carbonyl sulfide. In the presence of t-butyl peroxide, high yields of sulfides were obtained. Key chemicals used in the process included cobalt carbonyl (Co2(CO)8), carbon monoxide (CO), and disulfides such as benzyl disulfide and phenyl disulfide, along with solvents like aqueous ethanol and benzene. The reactions resulted in the formation of thioesters and sulfides through a series of steps involving the formation of cobalt complexes and the insertion of carbon monoxide.

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