Diphenyl sulfoxide

Base Information

• Chemical Name: Diphenyl sulfoxide
• CAS No.: 945-51-7
• Molecular Formula: C12H10OS
• Molecular Weight: 202.277
• Hs Code.: 29309070
• European Community (EC) Number: 213-415-9
• NSC Number: 630195,6779
• UNII: 4V290005U9
• DSSTox Substance ID: DTXSID0022141
• Nikkaji Number: J7.183H
• Wikidata: Q27260538
• ChEMBL ID: CHEMBL336123
• Mol file: 945-51-7.mol

Synonyms:diphenyl sulfoxide;diphenylsulfoxide;phenyl sulfoxide

Chemical Property of Diphenyl sulfoxide

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 5.55E-05mmHg at 25°C
• Melting Point: 66-71 °C
• Refractive Index: 1.672
• Boiling Point: 357.6 °C at 760 mmHg
• Flash Point: 170.1 °C
• PSA: 36.28000
• Density: 1.25 g/cm³
• LogP: 3.71900
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• Water Solubility.: Soluble in water. Soluble in most organic solvents.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 202.04523611
• Heavy Atom Count: 14
• Complexity: 171

Purity/Quality:

Diphenyl sulfoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C1=CC=C(C=C1)S(=O)C2=CC=CC=C2
• Uses: Diphenyl sulfoxide is a reagent used as an oxidant and hydroxyl activator in combination with a variety of electrophilic reagents. Efficient glycosidation of a phenyl thiosialoside donor with diphenyl sulfoxide and triflic anhydride in dichloromethane was reported. Direct glycosylations with 1-hydroxy glycosyl donors is made using trifluoromethanesulfonic anhydride and diphenyl sulfoxide. The preparation of triarylsulfonium halides was by the action of aryl Grignard reagents on diphenyl sulfoxide.

Technology Process of Diphenyl sulfoxide

There total 200 articles about Diphenyl sulfoxide 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: 93.0%

2,4,6-trimethyl-pyridine (108-75-8) + diphenyl sulfide (139-66-2) → 2,4,6-trimethyl-pyridine 1-oxide (3376-50-9) + 1,1'-sulfinylbisbenzene (945-51-7)

Guidance literature:

With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; dihydrogen peroxide; at 25 ℃; chemoselective reaction; Neat (no solvent);

DOI:10.1021/jo1011784

Reference yield: 76.0%

diphenyl sulfide (139-66-2) + 3-diazo-2-butanone (14088-58-5) → 1,1'-sulfinylbisbenzene (945-51-7) + acetic anhydride (108-24-7) + dimethylglyoxal (431-03-8)

Guidance literature:

With oxygen; at -78 - 25 ℃; Product distribution; Mechanism; TPP as sensitizer;

DOI:10.1016/S0040-4039(00)86887-2

Reference yield: 73.0%

diphenyl sulfide (139-66-2) → 3,4-dihydroisoquinoline (3230-65-7) + 1,1'-sulfinylbisbenzene (945-51-7)

Guidance literature:

With oxaziridine 1; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/0040-4039(88)85218-3

upstream raw materials:

ethylene sulfite

diethyl ether

2-oxo-1,3,2-dioxathiane

5.5-dimethyl-1,3,2-dioxathiane-2-oxide

Downstream raw materials:

bis(3-nitrophenyl)sulfoxide

benzaldehyde

benzyl phenyl sulfoxide

4-Benzylbenzoic acid

Refernces

• 1、 Kargar, Hadi,Moghimi, Atefeh,Fallah-Mehrjardi, Mehdi,Behjatmanesh-Ardakani, Reza,Rudbari, Hadi Amiri,Munawar, Khurram Shahzad. "New oxovanadium and dioxomolybdenum complexes as catalysts for sulfoxidation: experimental and theoretical investigations of E and Z isomers of ONO tridentate Schiff base ligand". . p. 22 - 36. Retrieved 2021/06/23.
• 2、 Lee, Sunwoo,Park, Jin Kyu. "Sulfoxide and Sulfone Synthesis via Electrochemical Oxidation of Sulfides". . p. 13790 - 13799. Retrieved 2021/10/12.