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

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

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 
• 616-42-2 dimethylsulfite 
• 625-01-4 ethyl chlorosulfate 
• 28715-70-0 methoxy-phenyl-sulfane 
• 623-81-4 diethyl sulphite 
• 139-66-2 diphenyl sulfide 
• 1066-30-4 chromium(lll) acetate 
• 1859-03-6 ethyl benzenesulfinate 
• 13086-77-6 benzenesulfinic anhydride 
• 98-09-9 benzenesulfonyl chloride 
• 618-41-7 Benzenesulfinic acid 
• 960-41-8 (E)-1-phenyl-3-(phenylsulfonyl)prop-2-en-1-one 
• 71-43-2 benzene 

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

New oxovanadium and dioxomolybdenum complexes as catalysts for sulfoxidation: experimental and theoretical investigations of E and Z isomers of ONO tridentate Schiff base ligand

A new ONO-tridentate Schiff base ligand (H2L) derived by the condensation of nicotinic hydrazide with 5-chlorosalicylaldehyde has been prepared and characterized by combustion analysis (CHN), FT-IR and multinuclear (1H and 13C) NMR spectroscopy. The crystalline nature and molecular structure of the ligand were confirmed by single-crystal X-ray diffraction analysis. Furthermore, the optimized structural parameters of the four possible configurations of the ligand including Z and E stereoisomers each containing two tautomeric forms (enol and keto) have also been investigated. The theoretical parameters were calculated by performing the DFT method using the B3LYP/Def2-TZVP level of theory. In addition to this, dioxomolybdenum(VI) (MoO2L) and oxovanadium(V) (VOL) complexes with the entitled Schiff base ligand have also been prepared and characterized by different techniques. Then, the catalytic efficiencies of synthesized VOL and MoO2L complexes were also explored for the oxidation of sulfides using 30% aqueous H2O2 as a source of oxygen. These homogeneous catalysts showed excellent catalytic activities in the oxidation of both aromatic and aliphatic sulfides.

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.

Sulfoxide and Sulfone Synthesis via Electrochemical Oxidation of Sulfides

The oxidation of diaryl sulfides and aryl alkyl sulfides to the corresponding sulfoxides and sulfones under electrochemical conditions is reported. Sulfoxides are selectively obtained in good yield under a constant current of 5 mA for 10 h in DMF, while sulfones are formed as the major product under a constant current of 10 or 20 mA for 10 h in MeOH. The oxygen of both the sulfoxide and sulfone function is derived from water.

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.

Organocatalytic sulfoxidation

Treatment of a sulfide with a catalytic amount of a 1,3-diketone in the presence of silica sulfuric acid as a co-catalyst and hydrogen peroxide (50% aq) as the stoichiometric oxidant leads to the corresponding sulfoxide product. The reaction is effective for diaryl, aryl-alkyl and dialkyl sulfides and is tolerant of oxidisable and acid sensitive functional groups. Investigations have shown that the tris-peroxide 2, formed on reaction of pentane-2,4-dione with hydrogen peroxide under acidic reaction conditions, can oxidise two equivalents of sulfide using the exocyclic peroxide groups whereas the endocyclic peroxide remains intact. Calculations provide a mechanism consistent with experimental observations and suggest the reaction proceeds via an initial acid catalysed ring opening of a protonated tris-peroxide prior to oxygen transfer to a sulfur nucleophile.

Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst

We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.

Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide

A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.

Synthesis method of diphenyl sulfoxide

The invention discloses a synthesis method of diphenyl sulfoxide. The synthesis method of the diphenyl sulfoxide comprises the following steps: 1) adding pure benzene and aluminum trichloride into a reactor, heating to 35 to 45 DEG C under stirring, adding sulfoxide chloride dropwise, continuously stirring and completely reacting at 30 to 60 DEG C to obtain a benzene solution of the diphenyl sulfoxide; and 2) adding the benzene solution of the diphenyl sulfoxide into water dropwise, performing hydrolysis, controlling the dropwise adding temperature to be less than 70 DEG C, and performing treatment and purification after complete hydrolysis to obtain the product diphenyl sulfoxide. The synthesis method of the diphenyl sulfoxide has the advantages of cheap and easily available raw materials, mild reaction condition, low energy consumption, simple process structure, easiness in operation and the like.

Selective and solventless oxidation of organic sulfides and alcohols using new supported molybdenum (VI) complex in microwave and conventional methods

A new dioxo-molybdenum (VI) complex supported on functionalized Merrifield resin (MR-Mo) has been synthesized and characterized by elemental, scanning electron mcroscopy, energy-dispersive X-ray analysis, TGA, Brunauer–Emmett–Teller method, powder-X-ray d