7397-10-6

Basic information

• Product Name: (+/-)-3-benzylthio-2-butanone
• Synonyms: (+/-)-3-benzylthio-2-butanone
• CAS NO: 7397-10-6
• Molecular Weight: 194.298
• Mol File: 7397-10-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (+/-)-3-benzylthio-2-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-3-benzylthio-2-butanone(7397-10-6)
• EPA Substance Registry System: (+/-)-3-benzylthio-2-butanone(7397-10-6)

Safety Data

• Hazardous Substances Data: 7397-10-6(Hazardous Substances Data)

Upstream product

• 77611-73-5 Acetoin-methansulfonat 
• 100-53-8 phenylmethanethiol 
• 2028-63-9 but-3-yn-2-ol 
• 4091-39-8 3-chloro-2-butanone 
• 10230-69-0 benzylthioacetone 
• 74-88-4 methyl iodide 

Downstream Products

• 117139-68-1 4-Benzylsulfanyl-3,4-dimethyl-hexan-3-ol 
• 117139-81-8 3-Benzylsulfanyl-3-methyl-pentan-2-ol 
• 718-20-7 3-benzylthio-3-methylpentan-2-one 

Relevant articles and documents

Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives

The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling.

PREPARATION OF [ALPHA]-SULFENYLATED CARBONYL COMPOUNDS FROM PROPARGYLIC ALCOHOLS IN ONE STEP

The present relates to a method and a kit to produce an optically pure α-sulfenylated carbonyl compound comprising a primary or a secondary propargylic alcohol and an aryl thiol, a transition metal catalyst and a solvent.

α-Thio-substituted Ketones as Precursors of Olefins via Oxathiolanes: Benzyl as Protecting Group

The feasibility of a regiospecific synthesis of tetrasubsituted olefins starting from protected α-thiol substituted ketones has been demonstrated by three examples.The approach (see Scheme) involves: S-activated alkylation (i), carbonyl addition of an organometallic reagent (ii), deprotection (iii), formation of a 2-phenyloxathiolane (iv), and base-promoted cycloelimination (v).An unsatisfactory feature is the lack of stereochemical control in step (ii).An attempt to telescope steps (iii) and (iv) by sequential Pummerer reaction-cyclisation at the β-benzylthio alcohol stage was unsuccessful.