5310-17-8

Basic information

• Product Name: N-(4-Methylphenyl)ethanethioamide
• Synonyms: N-(4-Methylphenyl)ethanethioamide;N-(P-TOLYL)ETHANETHIOAMIDE
• CAS NO: 5310-17-8
• Molecular Formula: C₉H₁₁NS
• Molecular Weight: 165.2553
• Mol File: 5310-17-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 244.6°Cat760mmHg
• Flash Point: 101.7°C
• Appearance: /
• Density: 1.126g/cm³
• Vapor Pressure: 0.0301mmHg at 25°C
• Refractive Index: 1.636
• CAS DataBase Reference: N-(4-Methylphenyl)ethanethioamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Methylphenyl)ethanethioamide(5310-17-8)
• EPA Substance Registry System: N-(4-Methylphenyl)ethanethioamide(5310-17-8)

Safety Data

• Hazardous Substances Data: 5310-17-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H11NS/c1-7-3-5-9(6-4-7)10-8(2)11/h3-6H,1-2H3,(H,10,11)

Upstream product

• 2089-33-0 4-methylacethophenone oxime 
• 98-09-9 benzenesulfonyl chloride 
• 14277-01-1 N-(4-methylphenyl)acetamidine 
• 106-49-0 p-toluidine 
• 62-55-5 thioacetamide 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 540-23-8 p-toluidine hydrochloride 
• 5816-98-8 ethyl 2-((4-methylphenyl)carbamothioyl)-3-oxobutanoate 
• 193765-64-9 4-bromophenyl dithioacetate 
• 193765-63-8 4-chlorophenyl dithioacetate 
• 193765-62-7 4-methylphenyl dithioacetate 
• 36797-15-6 phenyl dithioacetate 
• 103-89-9 4-Methylacetanilide 
• 90922-20-6 N-p-tolyl-3-thio-malonamic acid 

Downstream Products

• 2941-71-1 2,6-dimethylbenzothiazole 
• 103-89-9 4-Methylacetanilide 
• 5132-17-2 N,N'-di(p-tolyl)acetamidine 
• 40746-60-9 5-methyl-1-(4-methylphenyl)-1H-tetrazole 

Relevant articles and documents

Contribution of Solvents to Geometrical Preference in the Z/ E Equilibrium of N-Phenylthioacetamide

We studied the Z/E preference of N-phenylthioacetamide (thioacetanilide) derivatives in various solvents by means of 1H NMR spectroscopy, as well as molecular dynamics (MD) and other computational analyses. Our experimental results indicate that the Z/E isomer preference of secondary (NH)thioamides of N-phenylthioacetamides shows substantial solvent dependency, whereas the corresponding amides do not show solvent dependency of the Z/E isomer ratios. Detailed study of the solvent effects based on molecular dynamics simulations revealed that there are two main modes of hydrogen (H)-bond formation between solvent and (NH)thioacetamide, which influence the Z/E isomer preference of (NH)thioamides. DFT calculations of NH-thioamide in the presence of one or two explicit solvent molecules in the continuum solvent model can effectively mimic the solvation by multiple solvent molecules surrounding the thioamide in MD simulations and shed light on the precise nature of the interactions between thioamide and solvent. Orbital interaction analysis showed that, counterintuitively, the Z/E preference of NH-thioacetamides is mainly determined by steric repulsion, while that of sterically congested N-methylthioacetamides is mainly determined by thioamide conjugation.

Transamidation of thioacetamide catalyzed by SbCl3

A transamidation reaction of thioacetamide with primary and secondary amines is described. The use of catalytic amounts of SbCl3 notably increases the yields and diminishes the reaction times. Typically, the amines should be aliphatic, but aromatic amines can be used as well, though with lower yields. This is one of the few examples where antimony has been used as a catalyst in organic reactions.

O,O-Diethyl dithiophosphoric acid mediated direct synthesis of thioamides from aldehydes and ketones

A general and convenient method for a one-pot conversion of aldehydes and ketones into thioamides has been developed. The protocol involves oximation of aldehydes and ketones followed by deoxygenative thioamidation of oximes with O,O-diethyl dithiophosphoric acid which acts as an acid as well a source of sulfur. The method is operationally simple, high yielding, and also applicable to the conversion of amides and nitriles into the corresponding thioamides.