470458-71-0

Basic information

• Product Name: 2-bromo-3-(phenylsulfanyl)cyclohex-2-en-1-one
• Synonyms: 2-bromo-3-(phenylsulfanyl)cyclohex-2-en-1-one
• CAS NO: 470458-71-0
• Molecular Weight: 283.189
• Mol File: 470458-71-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-bromo-3-(phenylsulfanyl)cyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-3-(phenylsulfanyl)cyclohex-2-en-1-one(470458-71-0)
• EPA Substance Registry System: 2-bromo-3-(phenylsulfanyl)cyclohex-2-en-1-one(470458-71-0)

Safety Data

• Hazardous Substances Data: 470458-71-0(Hazardous Substances Data)

Upstream product

• 77708-66-8 3-oxocyclohex-1-en-1-yl 4-methylbenzenesulfonate 
• 504-02-9 1,3-cylohexanedione 
• 882-33-7 diphenyldisulfane 
• 72031-35-7 2-bromo-3-hydroxycyclohex-2-enone 
• 108-98-5 thiophenol 
• 60060-44-8 2-bromocyclohexane-1,3-dienone 
• 75717-39-4 3-(phenylsulfanyl)cyclohex-2-en-1-one 

Downstream Products

• 14965-37-8 m-hydroxyphenyl phenyl sulfide 
• 470458-67-4 (S)-1-(t-butyldimethylsiloxy)-2-{3'-[N-(carbomethoxy)-N-(phenylselanylmethyl)amino]}-propyl-3-phenylsulfonyl-2-cyclohexene 
• 470458-78-7 1-(t-butyldimethylsiloxy)-2-{3'-[N-(carbomethoxy)-N-(hydroxymethyl)amino]}propyl-3-phenylsulfonyl-2-cyclohexene 
• 470458-68-5 (6R,7S,11S)-7-(t-butyldimethylsiloxy)-2-carbomethoxy-11-phenylsulfonyl-2-aza-spiro(5.5)undecane 
• 470458-66-3 1-(t-butyldimethylsiloxy)-2-(3'-carbomethoxyamino)propyl-3-phenylsulfonyl-2-cyclohexene 
• 470458-65-2 1-(t-butyldimethylsiloxy)-2-(3'-carbomethoxyamino)propyl-3-phenylthio-2-cyclohexene 
• 470458-73-2 (S)-Acetoxy-phenyl-acetic acid (S)-2-bromo-3-phenylsulfanyl-cyclohex-2-enyl ester 
• 470458-64-1 1-(t-butyldimethylsiloxy)-2-bromo-3-phenylthio-2-cyclohexene 
• 779343-39-4 1-(t-butyldimethylsiloxy)-2-bromo-3-phenylthio-2-cyclohexene 
• 470458-72-1 2-bromo-3-phenylthio-2-cyclohexen-1-ol 
• 900493-57-4 carbonic acid allyl ester 6-bromo-2-methyl-5-phenylsulfanyl-cyclohexa-1,5-dienyl ester 
• 470458-77-6 2-bromo-1-phenylsulfanyl-cyclohex-1-en-3-ol 

Relevant articles and documents

Formation of meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols from cyclohexane-1,3-diones

Reaction of cyclohexane-1,3-diones with TsCl/Et3N and treatment of the resulting 3-(tosyloxy)cyclohex-2-en-1-ones with aryl- or alkyl thiols and K2CO3 in MeCN gives 3-(arylsulfanyl)cyclohex-2-en-1-ones or 3-(alkylsulfanyl)cyclohex-2-en-1-ones, respectively. These compounds are easily brominated at C-2 by using NBS in MeCN; exposure to DBU in MeCN at room temperature then causes aromatization to afford meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols.

6-Exo-spiro (alkoxycarbonylamino)methyl radical cyclization: highly regio- and stereoselective synthesis of (-)-sibirine.

[reaction: see text] The (methoxycarbonylamino)methyl radical can be readily generated from its PhSe precursor and undergoes preferential 6-exo-spiro cyclization when PhSO(2) is attached at the distal alkene carbon. This property was applied to the synthe