4285-49-8

Basic information

• Product Name: Benzene, (3-butenylthio)-
• Synonyms: 3-butenyl phenyl sulfide;homoallyl phenyl sulfide;phenyl but-3-enyl sulfide
• CAS NO: 4285-49-8
• Molecular Formula: C10H12S
• Molecular Weight: 164.271
• Mol File: 4285-49-8.mol
• Article Data: 28

Chemical Properties

• CAS DataBase Reference: Benzene, (3-butenylthio)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (3-butenylthio)-(4285-49-8)
• EPA Substance Registry System: Benzene, (3-butenylthio)-(4285-49-8)

Safety Data

• Hazardous Substances Data: 4285-49-8(Hazardous Substances Data)

Upstream product

• 13307-75-0 (phenylthio)methyllithium 
• 106-95-6 allyl bromide 
• 40671-34-9 4-methanesulfonyloxy-1-butene 
• 930-69-8 sodium thiophenolate 
• 10437-85-1 cyclobutyl 4-methylbenzenesulfonate 
• 108-98-5 thiophenol 
• 14660-38-9 Δ³-butenylmercury chloride 
• 106-99-0 buta-1,3-diene 
• 1616562-91-4 (2-azidoallyl)(phenyl)sulfane 
• 762-72-1 allyl-trimethyl-silane 
• 5651-88-7 phenyl propargyl sulfide 
• 778-29-0 but-3-enyl 4-methylbenzenesulfonate 
• 110-01-0 thiophene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Downstream Products

• 67100-44-1 (but-3-en-1-ylsulfonyl)benzene 
• 182140-23-4 [Pd(Br)(C₆H₅SC₂H₄CHCH₂C₆F₅)]2 
• 1256168-95-2 1-(2-hydroxy-5-methoxyphenyl)-2-methyl-4-(phenylthio)butan-1-one 
• 1256168-93-0 methyl 4-hydroxy-3-(2-methyl-4-(phenylthio)butanoyl)benzoate 
• 1256169-11-5 1-(2-hydroxyphenyl)-5-(phenylthio)pentan-1-one 
• 1256168-90-7 1-(2-hydroxyphenyl)-2-methyl-4-(phenylthio)butan-1-one 
• 1256168-97-4 1-(2-hydroxy-6-methylphenyl)-2-methyl-4-(phenylthio)butan-1-one 
• 1256168-96-3 1-(2-hydroxy-3-methoxyphenyl)-2-methyl-4-(phenylthio)butan-1-one 
• 1256168-92-9 1-(5-chloro-2-hydroxyphenyl)-2-methyl-4-(phenylthio)butan-1-one 
• 65094-86-2 S-(but-3-en-1-yl)-S-phenyl-N-(p-tolylsulfonyl)sulfimide 

Relevant articles and documents

A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent

A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.

Catalytic Hydrothiolation: Counterion-Controlled Regioselectivity

In this Article, we expand upon the catalytic hydrothiolation of 1,3-dienes to afford either allylic or homoallylic sulfides with high regiocontrol. Mechanistic studies support a pathway in which regioselectivity is dictated by the choice of counterion associated with the Rh center. Non-coordinating counterions, such as SbF6-, allow for η4-diene coordination to Rh complexes and result in allylic sulfides. In contrast, coordinating counterions, such as Cl-, favor neutral Rh complexes in which the diene binds η2 to afford homoallylic sulfides. We propose mechanisms that rationalize a fractional dependence on thiol for the 1,2-Markovnikov hydrothiolation while accounting for an inverse dependence on thiol in the 3,4-anti-Markovnikov pathway. Through the hydrothiolation of an essential oil (β-farnesene), we achieve the first enantioselective synthesis of (-)-agelasidine A.

Interruption of Formal Schmidt Rearrangement/Hosomi-Sakurai Reaction of Vinyl Azides with Allyl/Propargylsilanes

An interrupted Schmidt rearrangement/Hosomi-Sakurai reaction of N-tosyl and S-substituted vinyl azides is reported. With BF3·Et2O as a Lewis acid promoter, the denitrogenative fragmentation of vinyl azides facilitates the generation of the N/S-stabilized carbocations, which further undergo nucleophilic addition by allyl/propargylsilanes for C-C bond formation. As a result, a variety of homoallylic/allenylic amines can be afforded in good yields under mild reaction conditions with well-defined functional-group tolerance.