88358-49-0

Basic information

• Product Name: Benzenemethanol, a-(mercaptomethyl)-, O-acetate
• CAS NO: 88358-49-0
• Molecular Formula: C10H12O2S
• Molecular Weight: 196.27
• Mol File: 88358-49-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, a-(mercaptomethyl)-, O-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-(mercaptomethyl)-, O-acetate(88358-49-0)
• EPA Substance Registry System: Benzenemethanol, a-(mercaptomethyl)-, O-acetate(88358-49-0)

Safety Data

• Hazardous Substances Data: 88358-49-0(Hazardous Substances Data)

Upstream product

• 96-09-3 styrene oxide 
• 507-09-5 tiolacetic acid 

Downstream Products

• 115120-25-7 Acetic acid (S)-phenyl-(1S,3R,4R)-2-thia-bicyclo[2.2.1]hept-5-en-3-yl-methyl ester 
• 115120-25-7 Acetic acid (R)-phenyl-(1S,3R,4R)-2-thia-bicyclo[2.2.1]hept-5-en-3-yl-methyl ester 
• 115120-25-7 Acetic acid (1R,3R,4S)-phenyl-2-thia-bicyclo[2.2.1]hept-5-en-3-yl-methyl ester 
• 88358-43-4 2-acetoxy-2-phenylethyl phenacyl sulfide 

Relevant articles and documents

Diastereoselectivity in the Diels-Alder Reactions of Thioaldehydes

The Diels-Alder reaction of thioaldehydes with cyclopentadiene occurs with a preference for the endo isomer.The highest selectivity is observed for thioaldehydes RCHS where R is a bulky group such as tert-butyl or isopropyl.Thioaldehydes having α-alkoxy, acetoxy, or siloxy substituents also react with useful endo selectivity.Secondary orbital overlap is a small factor in these reactions since α-oxo thioaldehydes react with relatively low endo selectivity.Steric effects are primarily responsible for the endo preferences observed.The Diels-Alder reactions of chiral α-oxygen substituted thioaldehydes also occur with useful thioformyl face selectivity.A Cornforth transition state 5 is most likely for the selectivity observed for α-alkoxy or acetoxy thioaldehydes, but the α-hydroxy analogue 23 reacts with the opposite facial preference.The highest face selectivity is obtained with the acetonide of thioglyceraldehyde, generated by photolysis of the phenacyl sulfide 15b.