1404374-16-8

Basic information

• Product Name: C₁₄H₁₂N₂OS₂
• Synonyms: C₁₄H₁₂N₂OS₂
• CAS NO: 1404374-16-8
• Molecular Weight: 288.394
• Mol File: 1404374-16-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₁₄H₁₂N₂OS₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₄H₁₂N₂OS₂(1404374-16-8)
• EPA Substance Registry System: C₁₄H₁₂N₂OS₂(1404374-16-8)

Safety Data

• Hazardous Substances Data: 1404374-16-8(Hazardous Substances Data)

Upstream product

• 101-02-0 triphenyl phosphite 
• 1404374-18-0 3-phenylthio-1,2,4-dithiazole-5-one 
• 62-53-3 aniline 

Relevant articles and documents

1,2,4-Dithiazole-5-ones and 5-thiones as efficient sulfurizing agents of phosphorus(iii) compounds - A kinetic comparative study

The sulfurization efficiency of 25 3-substituted-1,2,4-dithiazole-5-ones and 5-thiones towards triphenyl phosphite in acetonitrile, DCM, THF and toluene at 25 °C was evaluated. All the 1,2,4-dithiazoles are much better sulfurizing reagents than commercially available agents (PADS, TETD, Beaucage's reagent). The most efficient sulfurizing agents in all solvents are 3-phenoxy (4), 3-phenylthio (5) and 3-ethoxy-1,2,4-dithiazole-5-one (1) whose reactivity is at least two orders of magnitude higher than that of other 1,2,4-dithiazoles. Contrary to a previous report, the sulfurization with 1 does not yield carbonylsulfide and ethyl cyanate as the additional reaction products but unstable ethoxythiocarbonyl isocyanate which has been trapped with 4-methoxyaniline. Similar trapping experiments have proven that the site of attack is at the sulfur adjacent to the CO group for compounds 4 and 5. The reaction pathway involves rate-limiting initial nucleophilic attack of the phosphorus at sulfur followed by decomposition of the phosphonium intermediate to the corresponding phosphorothioate and isocyanate/isothiocyanate species. The existence of the phosphonium intermediate during sulfurization of triphenyl phosphine with 3-phenyl-1,2,4-dithiazole-5-thione (7a) was proven using kinetic studies. From the Hammett and Bronsted correlations and from other kinetic measurements it was concluded that the transition-state structure is almost apolar for the most reactive 1,2,4-dithiazoles whereas a polar structure resembling a zwitter-ionic intermediate may be more appropriate for the least reactive 1,2,4-dithiazoles. The extent of P-S bond formation and S-S bond cleavage is very similar in all reaction series but it gradually decreases with the reactivity of the 1,2,4-dithiazole derivatives.