200562-81-8

Basic information

• Product Name: 3-Hydroxy-N,N-dimethyl-4-phenyl-thiobutyramide
• CAS NO: 200562-81-8
• Molecular Weight: 223.339
• Mol File: 200562-81-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-Hydroxy-N,N-dimethyl-4-phenyl-thiobutyramide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-N,N-dimethyl-4-phenyl-thiobutyramide(200562-81-8)
• EPA Substance Registry System: 3-Hydroxy-N,N-dimethyl-4-phenyl-thiobutyramide(200562-81-8)

Safety Data

• Hazardous Substances Data: 200562-81-8(Hazardous Substances Data)

Upstream product

• 631-67-4 N,N-dimethylthioacetamide 
• 122-78-1 phenylacetaldehyde 

Relevant articles and documents

Stereocontrolled Thio-Claisen rearrangement of S-allylic ketene aminothioacetals by an hydroxysubstituted adjacent stereogenic centre

(Z)-S-alkylic ketene aminothioacetals were prepared from N,N-Dimethyl β-hydroxythioamides 2-8 by deprotonation with LDA (2 eq.) at -78°C followed by S-alkylation with allylic bromide. Rearrangement of these compounds occured easily at room temperature affording major syn N,N-dimethyl β-hydroxy α-allylic thioamides 9-21 with a syn/anti ratio of 80/20 to 98/2. The syn configuration of the major diastereoisomer was confirmed by an univocal synthesis of syn thioamides 9 and 11. The structure assignments were confirmed by empirical 13C NMR rules. The observed induction is well suppported by a proposed transition state model.