71778-41-1

Basic information

• Product Name: 2-[bis(phenylthio)methyl]furan
• Synonyms: 2-[bis(phenylthio)methyl]furan
• CAS NO: 71778-41-1
• Molecular Weight: 298.43
• Mol File: 71778-41-1.mol

Chemical Properties

• CAS DataBase Reference: 2-[bis(phenylthio)methyl]furan(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[bis(phenylthio)methyl]furan(71778-41-1)
• EPA Substance Registry System: 2-[bis(phenylthio)methyl]furan(71778-41-1)

Safety Data

• Hazardous Substances Data: 71778-41-1(Hazardous Substances Data)

Upstream product

• 98-01-1 furfural 
• 95-14-7 1,2,3-Benzotriazole 
• 108-98-5 thiophenol 
• 18708-18-4 furfural tosylhydrazone 
• 882-33-7 diphenyldisulfane 
• 1453-62-9 2-furaldehyde dimethyl acetal 
• 270918-58-6 (E)-5-(Phenylthio)pent-2-en-4-inal 

Downstream Products

• 98-01-1 furfural 
• 1027311-87-0 3-[(3-Benzyloxy-phenyl)-hydroxy-methyl]-4-(furan-2-yl-bis-phenylsulfanyl-methyl)-dihydro-furan-2-one 

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Surprising reaction of 5-(phenylthio)- and 5-(methylthio)pent-2-en-4- inal with HCl

Contrary to expectations (Scheme 1), 5-(phenylthio)-(1a) as well as 5- (methylthio)pent-2-en-4-inal (1b) react with a slight excess of HCl to give 2-[bis(phenylthio)mcthyl]furan (17a, 77% yield) and 2- [bis(methylthio)methyl]furan (17b, 61% yield), respectively. Structures 17a and 17b are supported by the results of an X-ray crystal-structure analysis, by spectroscopic data in comparison to those of model compounds, and by synthesis of 17a. This surprising reaction is tentatively explained by a mechanism (Scheme 4), including a special pyran → furan ring-contraction sequence, which is in agreement with a labelling experiment.

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