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945-51-7

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945-51-7 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

Check Digit Verification of cas no

The CAS Registry Mumber 945-51-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,4 and 5 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 945-51:
(5*9)+(4*4)+(3*5)+(2*5)+(1*1)=87
87 % 10 = 7
So 945-51-7 is a valid CAS Registry Number.
InChI:InChI=1/C12H10OS/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H

945-51-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (D1002)  Diphenyl Sulfoxide  >99.0%(GC)

  • 945-51-7

  • 5g

  • 180.00CNY

  • Detail
  • TCI America

  • (D1002)  Diphenyl Sulfoxide  >99.0%(GC)

  • 945-51-7

  • 25g

  • 560.00CNY

  • Detail
  • TCI America

  • (D1002)  Diphenyl Sulfoxide  >99.0%(GC)

  • 945-51-7

  • 100g

  • 1,230.00CNY

  • Detail
  • Alfa Aesar

  • (B22135)  Diphenyl sulfoxide, 98+%   

  • 945-51-7

  • 25g

  • 573.0CNY

  • Detail
  • Alfa Aesar

  • (B22135)  Diphenyl sulfoxide, 98+%   

  • 945-51-7

  • 100g

  • 1761.0CNY

  • Detail
  • Alfa Aesar

  • (B22135)  Diphenyl sulfoxide, 98+%   

  • 945-51-7

  • 500g

  • 7479.0CNY

  • Detail
  • Aldrich

  • (P35405)  Diphenylsulfoxide  96%

  • 945-51-7

  • P35405-25G

  • 496.08CNY

  • Detail
  • Aldrich

  • (P35405)  Diphenylsulfoxide  96%

  • 945-51-7

  • P35405-100G

  • 1,772.55CNY

  • Detail

945-51-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Phenyl sulfoxide

1.2 Other means of identification

Product number -
Other names Benzene, 1,1‘-sulfinylbis-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:945-51-7 SDS

945-51-7Relevant articles and documents

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

Lhoták, Pavel,Morávek, Ji?í,?mejkal, Tomá?,Stibor, Ivan,Sykora, Jan

, p. 7333 - 7336 (2003)

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

Kargar, Hadi,Kaka-Naeini, Azar,Fallah-Mehrjardi, Mehdi,Behjatmanesh-Ardakani, Reza,Amiri Rudbari, Hadi,Munawar, Khurram Shahzad

, p. 1563 - 1583 (2021/05/11)

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.

Organocatalytic sulfoxidation

Davidson, Stuart C.,Gomes, Gabriel dos Passos,Kuhn, Leah R.,Alabugin, Igor V.,Kennedy, Alan R.,Tomkinson, Nicholas C.O.

, (2020/12/07)

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.

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