156730-69-7

Basic information

• Product Name: 2-Phenylthiohexansaeureethylester
• Synonyms: 2-Phenylthiohexansaeureethylester
• CAS NO: 156730-69-7
• Molecular Weight: 252.378
• Mol File: 156730-69-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Phenylthiohexansaeureethylester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenylthiohexansaeureethylester(156730-69-7)
• EPA Substance Registry System: 2-Phenylthiohexansaeureethylester(156730-69-7)

Safety Data

• Hazardous Substances Data: 156730-69-7(Hazardous Substances Data)

Upstream product

• 109-65-9 1-bromo-butane 
• 7605-25-6 ethyl phenylsulfenylacetate 
• 615-96-3 Ethyl 2-bromohexanoate 
• 108-98-5 thiophenol 
• 133-08-4 diethyl butylmalonate 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 144076-89-1 ethyl 2-(phenylsulfonyl)hexanoate 
• 911239-41-3 2-phenylsulfanyl-hexan-1-ol 
• 52190-44-0 2-(Phenylthio)hexanal 
• 711028-29-4 (E)-5-Phenylsulfanyl-non-3-en-2-one 

Relevant articles and documents

Stannyl radical-mediated cleavage of π-deficient heterocyclic sulfones. Synthesis of α-fluoro esters and the first homonucleoside α-fluoromethylene phosphonate

-

Stannyl radical-mediated cleavage of π-deficient heterocyclic sulfones. Synthesis of α-fluoro esters

Treatment of ethyl 2-(pyridin-2-ylsulfonyl)hexanoate with tributylstannane and azobis(2-methyl-2-propanitrile) (AIBN) in benzene at reflux for 36 h resulted in hydrogenolysis to give ethyl hexanoate (60%), whereas no reaction was observed after 48 h at reflux with ethyl 2-(phenylsulfonyl)-hexanoate. Ethyl 2-(pyrimidin-2-ylsulfonyl)hexanoate underwent quantitative hydrogenolysis within 1 h under these conditions. This represents a mild new methodology for removal of the synthetically useful sulfone moiety. Substitution of Bu3SnD for Bu3SnH gave access to α-deuterium-labeled esters. Treatment of the α-(pyrimidin-2-ylsulfonyl) enolates derived from several esters with Selectfluor gave high yields of the 2-fluoro-2-(pyrimidin-2-ylsulfonyl)alkanoates, which were smoothly desulfonylated [Bu3SnH (2 equiv)/AIBN/benzene/Δ] to give 2-fluoroalkanoates. "Catalytic" tin hydride, generated from tribuytltin chloride (0.15 equiv) and excess polymethylhydrosiloxane in the presence of potassium fluoride, also effected removal of the π-deficient α-(pyrimidin-2-ylsulfonyl) moiety from acid derivatives in high yields. Desulfonylation is suggested to proceed via alkoxy ketyl-type radicals and tin enolates.