1416132-20-1

Basic information

• Product Name: 1-amino-5-methylimidazole-2(3H)-thione
• Synonyms: 1-amino-5-methylimidazole-2(3H)-thione
• CAS NO: 1416132-20-1
• Molecular Weight: 129.186
• Mol File: 1416132-20-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-amino-5-methylimidazole-2(3H)-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-amino-5-methylimidazole-2(3H)-thione(1416132-20-1)
• EPA Substance Registry System: 1-amino-5-methylimidazole-2(3H)-thione(1416132-20-1)

Safety Data

• Hazardous Substances Data: 1416132-20-1(Hazardous Substances Data)

Upstream product

• 137768-73-1 1-isothiocyanatopropa-1,2-diene 

Relevant articles and documents

Synthesis of unexpected bifunctionalized thiazoles by nucleophilic attack on allenyl isothiocyanate

Treatment of allenyl isothiocyanate with a variety of nucleophiles leads to 5-methylthiazoles with a functional group at the 2-position. The same pattern of reactivity is also seen with N-aminophthalimide. In the presence of azide salt, hydrazoic acid, or N,N-disubstituted hydroxylamines, however, allenyl isothiocyanate is converted into bifunctionalized thiazoles. We explain the formation of these products by nucleophilic addition at the isothiocyanato moiety followed by ring closure and an N-N or N-O cleavage reaction to generate short-lived 2-imino-5-methylidenethiazole or 5-methylidenethiazol-2-one. Such intermediates are trapped by addition reactions to give the final heterocyclic compounds. In the case of N,N-disubstituted hydroxylamines, the primary addition products with allenyl isothiocyanate can be detected as unstable intermediates by IR and NMR spectroscopy.