52417-37-5

Basic information

• Product Name: Benzeneethanethioamide, a-hydroxy-N,N,a-trimethyl-
• CAS NO: 52417-37-5
• Molecular Formula: C11H15NOS
• Molecular Weight: 209.312
• Mol File: 52417-37-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzeneethanethioamide, a-hydroxy-N,N,a-trimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneethanethioamide, a-hydroxy-N,N,a-trimethyl-(52417-37-5)
• EPA Substance Registry System: Benzeneethanethioamide, a-hydroxy-N,N,a-trimethyl-(52417-37-5)

Safety Data

• Hazardous Substances Data: 52417-37-5(Hazardous Substances Data)

Upstream product

• 98-86-2 acetophenone 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 758-16-7 N,N-dimethylthioformamide 

Downstream Products

• 139040-64-5 Trifluoro-acetic acid 1-dimethylthiocarbamoyl-1-phenyl-ethyl ester 
• 115245-19-7 4-Nitro-benzoic acid 1-dimethylthiocarbamoyl-1-phenyl-ethyl ester 

Relevant articles and documents

Napthalene-catalysed lithiation of carbamoyl and thiocarbamoyl chlorides under Barbier-type reaction conditions

The reaction of different carbamoyl or thiocarbamoyl chlorides 1 with carbonyl compounds or imines 2 in the presence of an excess of lithium powder and a catalytic amount of naphthalene (3 mol %) in THF at -78°C leads, after hydrolysis with water, to the

Solvolytic Elimination Reactions of Tertiary α-CSNMe2-Substitutedd Systems

The tertiary benzylic α-CSNMe2-substituted p-nitrobenzoates and trifluoroacetates of general structure Ar(CH3)C(CSNMe2)(OCOR), 7 and 8, solvolyze to give exclusively elimination products H2C=C(CSNMe2)Ar.A Hammett study gave a nonlinear correlation.Variation in rate with solvent ionizing power was small for the unsubstituted trifluoroacetate derivative of 8, and the β-CD3 isotope effect on rate was negligible.There is, however, a large isotope effect (2.5-2.8) in formation of the elimination product when Ph(CH2D)C(CSNMe2)(OCOCF3) solvolyzes.It is concluded that an intermediate must be involved sine the product-determining step and the rate-determining step have differing isotope effects.The likely intermediate is an α-CSNMe2-substituted cation as an ion pair), despite the fact that the reaction has few characteristics of a typical E1 reaction.Tertiary noorbornyl, cyclohexyl, and 2-propyl α-CSNMe2-substituted systems also react to give exclusively elimination products at rates far in excess of α-CONMe2 analogues.It is suggested that α-CSNMe2 cations are also intermediates and that these cations undergo proton loss at an early ion pair stage.These cations are proposed to derive substitantial stabilization by charge delocalization onto sulfur of the thiocarbonyl group. By way of contrast, the secondary system CH3CH(CSNMe2)(OCOCF3), 25, solvolyzes to give mainly a rearranged product CH3CH(CONMe2)(SCOCH3) via a KΔ mechanism involving neighboring thiocarbonyl participation leading to a cyclized ion.