945-51-7

Basic information

• Product Name: Phenyl sulfoxide
• Synonyms: 1,1’-sulfinylbis-benzen;1,1’-sulfinylbis-Benzene;Benzene, 1,1'-sulfinylbis-;Phenylsulfinylbenzene;Sulfoxide, diphenyl;sulfoxide,diphenyl;DIPHENYL SULFOXIDE;DIPHENYL SULPHOXIDE
• CAS NO: 945-51-7
• Molecular Formula: C₁₂H₁₀OS
• Molecular Weight: 202.27
• EINECS: 213-415-9
• Product Categories: Biochemistry;Reagents for Oligosaccharide Synthesis;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfoxides;Sulfur Compounds;fine chemicals
• Mol File: 945-51-7.mol
• Article Data: 261

Chemical Properties

• Melting Point: 69-71 °C(lit.)
• Boiling Point: 206-208 °C13 mm Hg(lit.)
• Flash Point: 206-208°C/13mm
• Appearance: White to off-white/Crystalline Powder
• Density: 1.1833 (rough estimate)
• Vapor Pressure: 5.55E-05mmHg at 25°C
• Refractive Index: 1.6090 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• Water Solubility: Soluble in water. Soluble in most organic solvents.
• BRN: 1908444
• CAS DataBase Reference: Phenyl sulfoxide(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl sulfoxide(945-51-7)
• EPA Substance Registry System: Phenyl sulfoxide(945-51-7)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: DA9185000
• TSCA: Yes
• Hazardous Substances Data: 945-51-7(Hazardous Substances Data)

Usage

Description

Phenyl sulfoxide, also known as diphenyl sulfoxide, is a white to off-white crystalline powder that serves as a reagent with properties of an oxidant and hydroxyl activator. It is commonly used in combination with various electrophilic reagents to facilitate chemical reactions.

Uses

Used in Organic Synthesis:
Phenyl sulfoxide is used as an oxidant and hydroxyl activator in organic synthesis, enabling efficient glycosidation of phenyl thiosialoside donors with triflic anhydride in dichloromethane. This application is crucial for the synthesis of complex carbohydrate structures and related compounds.
Used in Glycosylation Reactions:
Phenyl sulfoxide is utilized as a key component in direct glycosylations with 1-hydroxy glycosyl donors, in conjunction with trifluoromethanesulfonic anhydride. This combination allows for the formation of glycosidic bonds, which are essential in the synthesis of oligosaccharides and other carbohydrate-based molecules.
Used in the Preparation of Triarylsulfonium Halides:
Phenyl sulfoxide is used in the synthesis of triarylsulfonium halides through the action of aryl Grignard reagents on diphenyl sulfoxide. These triarylsulfonium salts are valuable intermediates in organic chemistry, particularly for the preparation of sulfonium ylides and other sulfur-containing compounds.

Synthesis Reference(s)

Journal of the American Chemical Society, 114, p. 6269, 1992 DOI: 10.1021/ja00041a069Tetrahedron Letters, 31, p. 4533, 1990 DOI: 10.1016/S0040-4039(00)97667-6

InChI:InChI=1/C12H10OS/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H

Upstream product

• 1003-85-6 5.5-dimethyl-1,3,2-dioxathiane-2-oxide 
• 60-29-7 diethyl ether 
• 98-09-9 benzenesulfonyl chloride 
• 618-41-7 Benzenesulfinic acid 
• 71-43-2 benzene 
• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 
• 75-91-2 tert.-butylhydroperoxide 
• 32133-82-7 Martins sulfurane 
• 34713-70-7 2-Phenylpropanal 
• 108770-97-4 4-pyridyl phenyl sulfoxide 
• 1016-82-6 1-benzenesulfinyl-4-chloro-benzene 
• 951-92-8 1-methoxyl-4-(phenylsulfinyl)benzene 
• 112921-52-5 o-bromophenyl phenyl sulfoxide 
• 71257-51-7 3-pyridyl phenyl sulfoxide 

Downstream Products

• 92695-58-4 bis(3-nitrophenyl)sulfoxide 
• 22731-83-5 S,S-diphenylsulphoximine 
• 7417-81-4 benzyl phenyl sulfoxide 
• 876494-48-3 benzenesulfinyl-phenyl-acetic acid 
• 139-66-2 diphenyl sulfide 
• 31688-57-0 (2,4-dimethyl-phenyl)-diphenyl sulfonium ; bromide 
• 3353-89-7 triphenylsulfonium bromide 
• 132-65-0 dibenzothiophene 
• 5181-10-2 bis(4-chlorophenyl)sulfide 
• 127-63-9 diphenyl sulphone 
• 1228-53-1 3,3'-dinitrodiphenyl sulfone 
• 13343-26-5 phenyl p-chlorophenyl sulfide 
• 3393-78-0 4,4'-dibromodiphenyl sulfide 
• 65662-88-6 phenyl(4-bromophenyl)sulfide 

Relevant articles and documents

Stereoselective oxidation of thiacalix[4]arenes with the NaNO 3/CF3COOH system

A series of alkyl substituted thiacalix[4]arene derivatives (being conformationally mobile or immobilised in the cone conformation) was used as the starting point for this study. It was demonstrated that the NaNO 3/CF3COOH system can

Oxovanadium and dioxomolybdenum complexes: synthesis, crystal structure, spectroscopic characterization and applications as homogeneous catalysts in sulfoxidation

New oxovanadium and dioxomolybdenum Schiff base complexes, [VO(L)(OCH3)] n and [MoO2(L)(CH3OH)], were synthesized by treating an ONO donor Schiff base (H2L) derived by condensation of 3-ethoxysalicylaldehyde and nicotinic hydrazide with oxo and dioxo acetylacetonate salts of vanadium and molybdenum (VO(acac)2 and MoO2(acac)2), respectively. The synthesized ligand and complexes were characterized by FTIR, multinuclear (1H, 13C) NMR, elemental and single crystal X-ray diffraction analysis. In both complexes, the geometry around the central metal ions was distorted octahedral as revealed by diffraction studies. Theoretical calculations of the synthesized compounds were carried out by DFT at B3LYP/Def2-TZVP level of theory, which showed good correlation with the experimental results. Moreover, the catalytic efficiency of both complexes was investigated by oxidizing aryl and alkyl sulfides in the presence of 30% H2O2 in ethanol.

Electrochemical Scalable Sulfoxidation of Sulfides with Molecular Oxygen and Water

An efficient and chemoselective synthesis of sulfoxides through the electrooxidation of sulfides has been well developed. This protocol takes advantage of electricity as the terminal oxidant and of molecular oxygen and water as the oxygen atom sources. A variety of structurally diverse sulfoxide compounds are assembled in moderate to excellent yields. The scaled-up reactions at 6–20 mmol show the good practicability and application potential of this methodology. A possible free radical mechanism has been proposed to rationalize the reaction procedure.