13884-92-9

Basic information

• Product Name: PHENYLTHIOMETHYL TRIPHENYLPHOSPHONIUM CHLORIDE
• Synonyms: PHENYLTHIOMETHYL TRIPHENYLPHOSPHONIUM CHLORIDE;(phenylmercaptomethyl)triphenylphosphonium chloride;(PHENYLTHIOMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE 98%;(Phenylthiomethyl)triphenylphosphonium chloride, 98+%;Triphenyl[(phenylthio)Methyl]phosphoniuM Chloride
• CAS NO: 13884-92-9
• Molecular Formula: C₂₅H₂₂PS*Cl
• Molecular Weight: 420.93
• Product Categories: Wittig Reagents
• Mol File: 13884-92-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 257-258°C
• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Methanol, Water
• CAS DataBase Reference: PHENYLTHIOMETHYL TRIPHENYLPHOSPHONIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLTHIOMETHYL TRIPHENYLPHOSPHONIUM CHLORIDE(13884-92-9)
• EPA Substance Registry System: PHENYLTHIOMETHYL TRIPHENYLPHOSPHONIUM CHLORIDE(13884-92-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 13884-92-9(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Pale Beige Solid

Uses

Different sources of media describe the Uses of 13884-92-9 differently. You can refer to the following data:
1. A Wittig reagent.
2. A Wittig reagent

InChI:InChI=1/C25H22PS.ClH/c1-5-13-22(14-6-1)26(23-15-7-2-8-16-23,24-17-9-3-10-18-24)21-27-25-19-11-4-12-20-25;/h1-20H,21H2;1H/q+1;/p-1

Upstream product

• 7205-91-6 phenylthiomethyl chloride 
• 603-35-0 triphenylphosphine 
• 34884-33-8 (phenylthio)-methylenetriphenylphosphorane 
• 98-88-4 benzoyl chloride 
• 874-60-2 4-methyl-benzoyl chloride 
• 142-61-0 Hexanoyl chloride 
• 75-36-5 acetyl chloride 
• 2373-51-5 chloro-methylsulfanyl-methane 
• 7205-94-9 chloromethyl phenyl sulfoxide 
• 1193-82-4 racemic methyl phenyl sulfoxide 

Downstream Products

• 29736-81-0 phenyl(3-phenylprop-1-enyl)sulfane 
• 22103-05-5 1-(phenylthio)-1-propene 
• 50550-52-2 1-butenyl phenyl sulfide 
• 33831-07-1 Phenyl-3,3,3-trifluoro-2-(trifluoromethyl)-propenylsulfid 
• 101910-04-7 (Z)-(3R,5R)-7-(2,4-Dichloro-phenyl)-1-phenylsulfanyl-hept-1-ene-3,5-diol 
• 123518-27-4 (Z)-4,5-di-O-acetyl-1,2-didehydro-1,2,6-trideoxy-3-O-methyl-1-(phenylthio)-L-arabino-hexose 
• 123518-23-0 (E)-4,5-di-O-acetyl-1,2-didehydro-1,2,6-trideoxy-3-O-methyl-1-(phenylthio)-L-arabino-hexose 
• 791-28-6 Triphenylphosphine oxide 
• 34884-33-8 (phenylthio)-methylenetriphenylphosphorane 
• 58431-67-7 Z-3,3-Dimethylbut-1-en-1-yl-phenylsulfid 
• 53847-74-8 E-3,3-Dimethylbut-1-en-1-yl-phenylsulfid 
• 58431-66-6 E-3-methyl-but-1-en-1-yl phenyl sulphide 
• 58431-65-5 Z-3-methyl-but-1-en-1-yl phenyl sulphide 
• 58431-64-4 1-(1-Phenylthioethyl)-triphenylphosphoniumiodid 

Relevant articles and documents

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Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts

Phosphines were previously unusable as Pummerer-type nucleophiles due to competing redox chemistry with sulfoxides. Here we circumvent this problem to achieve a formal phosphine Pummerer reaction that offers thioalkyl phosphonium salts that, in turn, give rise to diverse vinyl sulfides via Wittig olefinations. Thirty vinyl sulfides are thus prepared from (alkylthioalkyl)triphenyl phosphonium salts and aldehydes. The hydrolysis of these vinyl sulfides offers an efficient and versatile two-step one-carbon homologation of aldehydes to ketones.

Base-catalysed intramolecular hydroamination of vinyl sulfiies

Small amounts of n-butyllithium catalyse the highly efficient hydroamination of a large variety of vinyl sulfides. This novel methodology offers an easy access to a wide range of nitrogen heterocycles, including simple pyrrolidines and piperidines, as well as more complex bicyclic compounds. Subsequent transformations of the sulfur group led to the formation of functionalised alkaloid-like substructures. Wiley-VCH Verlag GmbH & Co. KGaA.

A simplified preparation of vinyl sulfides, selenides and tellurides by a Wittig-type reaction

The preparation of several vinyl sulfides, selenides and tellurides by Wittig-type reaction in a one-pot procedure is described. The chalcogenyl triphenylphosphoranes 3 are formed 'in situ' by the reaction of chloromethyl phenyl chalcogenide, potassium tert-butoxide and triphenylphosphine. Reaction of 3 with carbonyl compounds affords the vinyl chalcogenides 6-9 with preferential Z-configuration.