87797-69-1

Basic information

• Product Name: S-phenyl 3-(phenylthio)propanethioate
• Synonyms: S-phenyl 3-(phenylthio)propanethioate
• CAS NO: 87797-69-1
• Molecular Weight: 274.408
• Mol File: 87797-69-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: S-phenyl 3-(phenylthio)propanethioate(CAS DataBase Reference)
• NIST Chemistry Reference: S-phenyl 3-(phenylthio)propanethioate(87797-69-1)
• EPA Substance Registry System: S-phenyl 3-(phenylthio)propanethioate(87797-69-1)

Safety Data

• Hazardous Substances Data: 87797-69-1(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 814-68-6 acryloyl chloride 
• 5219-65-8 acide phenylthio-3 propanoique 
• 87797-68-0 S-phenyl 3-chlorothiopropionate 
• 20965-36-0 2-(phenylthio)tetrahydro-2H-pyran 
• 51849-21-9 β-(phenylthio)propionyl chloride 

Downstream Products

• 120453-97-6 S-phenyl (E)-3-(t-butylthio)propenethioate 
• 120454-09-3 S-phenyl (Z)-3-(t-butylthio)propenethioate 
• 120453-95-4 S-phenyl (E)-3-(phenylsulfinyl)propenethioate 
• 120453-94-3 S-phenyl (E)-3-(phenylthio)propenethioate 
• 120453-96-5 S-phenyl (E)-3-(phenylsulfonyl)propenethioate 
• 120453-93-2 3-Chloro-3-phenylsulfanyl-thiopropionic acid S-phenyl ester 

Relevant articles and documents

A general diastereoselective synthesis of spiroacetals related to those in ionophores via the reaction of lactones with cerium(III) γ-cerioalkoxide. MAD reverses the diastereoselectivity of the addition of methylmetallics to a β-keto ether

The following steps constitute a fairly general and stereoselective synthesis of spiroacetals. 1. Thiophenol is added to acrylic acid. 2. The latter is treated consecutively with butyllithium, CeCl3, and an organolithium compound. 3. The resulting 3-(phenylthio) ketone is either reduced in the presence of zinc ion to yield mainly one diastereomer or treated with methyllithium or methylmagnesium chloride in the presence or absence of methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD, 25) to yield selectively either of two diastereomeric 3-(phenylthio) alcohols. 4. The alcohol is treated with butyllithium, lithium 4,4'-di-tert-butylbiphenylide (LDBB), and CeCl3, to yield a cerium(III) γ-cerioalkoxide, which is added to a lactone, the reaction being quenched with acid. In the addition to the keto ether in the absence of MAD, methyllithium or methylmagnesium chloride give very predominantly the erythro alcohol, presumably via Cram's chelate model, while in the presence of excess MAD, the threo product is very predominant, possibly because each oxygen atom is complexed with the bulky aluminum reagent. The methodology is demonstrated by the preparation of diastereomeric spiroacetals related to those found in a number of natural ionophores by using as the reaction partner of the carboxylate salt, α-lithio tetrahydrofuran or tetrahydropyran, readily generated by reductive lithiation of the corresponding α-(phenylthio) heterocycle with LDBB, and by employing methylmetallics rather than reducing agents for the reaction with the ketone.

Novel Alumina-catalysed Reactions of Arylthioalkyl Halides and Related Compounds

Arylthioalkyl halides of the type ArS(CH2)nCl (Ar = phenyl or substituted phenyl, n = 1-4) undergo rearrangement on heating with neutral alumina to 1,n-bis(arylthio)alkanes of type ArS(CH2)nSAr in high yield.Similar rearrangements occur with some closely related structural types.The bis(arylthio)alkanes undergo further reaction with alumina at higher temperatures in air giving diaryl disulphides.Bis(o-iodophenylthio)methane eliminates iodine on heating with alumina, producing dibenzodithiepin.Some observations concerning the mechanism are presented.