5309-94-4

Basic information

• Product Name: Propanethioamide, N,N-dimethyl-
• CAS NO: 5309-94-4
• Molecular Formula: C5H11NS
• Molecular Weight: 117.215
• Mol File: 5309-94-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Propanethioamide, N,N-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanethioamide, N,N-dimethyl-(5309-94-4)
• EPA Substance Registry System: Propanethioamide, N,N-dimethyl-(5309-94-4)

Safety Data

• Hazardous Substances Data: 5309-94-4(Hazardous Substances Data)

Upstream product

• 758-96-3 N,N-dimethyl-propanamide 
• 758-16-7 N,N-dimethylthioformamide 
• 75-03-6 ethyl iodide 
• 540-54-5 1-Chloropropane 
• 68-12-2 N,N-dimethyl-formamide 
• 38341-88-7 prop-2-ynyl thiocyanate 
• 124-40-3 dimethyl amine 
• 42070-57-5 C₅H₉NS₂ 
• 924-45-8 O-ethyl thiopropionate 

Downstream Products

• 22650-98-2 S-(p-Brom-phenacyl)-N,N-dimethyl-thiopropionsaeureimidiumbromid 
• 85892-04-2 erythro-N,N-dimethyl-2-methyl-3-phenylthiopent-4-enamide 
• 85892-05-3 threo-N,N-dimethyl-2-methyl-3-phenylthiopent-4-enamide 
• 78175-63-0 2-(1-Hydroxy-cyclohexyl)-N,N-dimethyl-thiopropionamide 
• 26919-89-1 (1R,2R)-3-Dimethylamino-2-methyl-1-phenyl-propan-1-ol 
• 26919-89-1 (1RS,2SR)-3-(dimethylamino)-2-methyl-1-phenyl-1-propanol 
• 1182707-49-8 (2S,3R)-3-(4-bromophenyl)-3-(diphenylphosphorylamino)-N,N,2-trimethylpropanethioamide 
• 1182707-47-6 (2S,3R)-3-(diphenylphosphorylamino)-N,N,2-trimethyl-3-phenylpropanethioamide 
• 90421-20-8 2,N,N-Trimethyl-3-phenyl-3-trimethylsilanyloxy-thiopropionamide 
• 90421-20-8 2,N,N-Trimethyl-3-phenyl-3-trimethylsilanyloxy-thiopropionamide 
• 78175-70-9 2-(4-tert-Butyl-1-hydroxy-cyclohexyl)-N,N-dimethyl-thiopropionamide 
• 78175-71-0 2-(4-tert-Butyl-1-hydroxy-cyclohexyl)-N,N-dimethyl-thiopropionamide 
• 76454-71-2 (2S,3R)-3-Hydroxy-2,N,N-trimethyl-3-phenyl-thiopropionamide 
• 76454-71-2 (2S,3S)-3-Hydroxy-2,N,N-trimethyl-3-phenyl-thiopropionamide 

Relevant articles and documents

Transition-Metal-Free, General Construction of Thioamides from Chlorohydrocarbon, Amide and Elemental Sulfur

A general method for one-pot synthesis of thioamides is developed through a three-component reaction involving chlorohydrocarbon, amide and elemental sulfur. Such a strategy does not only avoid residual transition metal in the product but also prevent the generation of C?N coupling by-product. The latter is prone to be generated when alkane halide and amine are present. With the protocol proposed in this work, both alkyl and aryl thioamides can be obtained in moderate to excellent yields with a high tolerance of various functional groups. External oxidants are not required in the reaction. In addition, the reaction mechanisms are addressed using a combination of controlling experiments and quantum chemical calculations.

Gas-phase NMR studies of N,N-dimethylthioamides. Influence of the thiocarbonyl substituent on the internal rotation activation energies

Temperature-dependent gas-phase 1H NMR spectra of seven thiocarbonyl-substituted N,N-dimethylthioamides (YCSN(CH3)2) obtained at 300 MHz are consistent with the following free activation energies ΔG?298 (kcal mol-1): Y = H, 22.5 (0.1); CH3, 18.0 (0.1); F, 18.3 (0.1); Cl, 16.9 (0.2); CF3, 17.2 (0.1); CH2CH3, 17.6 (0.1); CH(CH3)2, 16.3 (0.1). The results are compared to condensed-phase values and to the corresponding gas-phase oxoamides.