66716-59-4

Basic information

• Product Name: 2-Hexanone, 1-(phenylthio)-
• CAS NO: 66716-59-4
• Molecular Formula: C12H16OS
• Molecular Weight: 208.324
• Mol File: 66716-59-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-Hexanone, 1-(phenylthio)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hexanone, 1-(phenylthio)-(66716-59-4)
• EPA Substance Registry System: 2-Hexanone, 1-(phenylthio)-(66716-59-4)

Safety Data

• Hazardous Substances Data: 66716-59-4(Hazardous Substances Data)

Upstream product

• 20261-68-1 1-chlorohexan-2-one 
• 108-98-5 thiophenol 
• 931-59-9 benzenesulfenyl chloride 
• 693-02-7 hex-1-yne 
• 110-59-8 pentanonitrile 
• 4832-52-4 tris(phenylthio)methane 
• 7031-27-8 (phenylthio)acetic acid chloride 
• 539-82-2 ethyl n-valerate 
• 103-04-8 (phenylthio)acetic acid 
• 64168-52-1 4'-nitrobenzenesulfenanilide 
• 86887-87-8 Hex-1-en-1-yl phenyl sulfide 
• 113450-77-4 N-methyl-N-(4-nitrophenyl)-N'-<1-(phenylthio)hex-1-en-2-yl>acetamidine 
• 123630-47-7 (E)-2-acetoxy-1-phenylthiohex-1-ene 
• 124277-29-8 N-(4-nitrophenyl)-N'-<1-(phenylthio)hex-1-en-2-yl>acetamidine 

Downstream Products

• 113093-50-8 1-benzenesulfonylhexan-2-one 
• 137524-56-2 β-keto S-phenyl thiohexanoate 
• 6395-83-1 α-keto methyl hexanoate 
• 137524-61-9 1,1-Dichloro-1-phenylsulfanyl-hexan-2-one 

Relevant articles and documents

Effective method of β-keto sulfones synthesis

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One electron transfer reaction of phenyl vinyl sulfides with dioxygen. The fate of the intermediate vinyl sulfide radical cations

Mild reaction of phenyl vinyl sulfides with dioxygen can lead to the eventual formation of rearranged vinyl sulfides and/or carbonyl-containing sulfide products, which are believed to result from decomposition of initially-formed vinyl sulfide radical cations. Supporting evidence is provided by the comparable findings obtained from the one electron oxidation of one vinyl sulfide by cerium (IV) ammonium nitrate.

Acetamidinosulphenylation of Alkynes via Electrophilic Addition of 4'-Substituted Benzenesulphenanilides in Acetonitrile

A number of 4'-substituted benzenesulphenanilides and N-methyl-4'-nitrobenzenesulphenanilide are shown to add to simple alkynes in acetonitrile in the presence of boron trifluoride-diethyl ether to give acetamidinovinyl sulphides in varying yields.Addition is largely favoured by dialkyl substitution on the alkyne and by electron-attracting anilide substituents.Moreover, the azasulphenylation adducts are produced with trans stereospecificity and high regioselectivity (Markovnikov orientation).A likely mechanism involves nucleophilic displacement by the alkyne at the activated sulphur of the anilide complexed with boron trifluoride leading to the initial formation of a thiirenium ion intermediate.Subsequent back-side attack of acetonitrile on the thiirenium ion gives a nitrilium ion which is ultimately trapped by the liberated arylamine.