1603826-50-1

Basic information

• Product Name: 6-benzyl-4-methyl-6H-pyrazolo[3,4-c]isothiazole-3-carbonitrile
• CAS NO: 1603826-50-1
• Molecular Weight: 254.315
• Mol File: 1603826-50-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 6-benzyl-4-methyl-6H-pyrazolo[3,4-c]isothiazole-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 6-benzyl-4-methyl-6H-pyrazolo[3,4-c]isothiazole-3-carbonitrile(1603826-50-1)
• EPA Substance Registry System: 6-benzyl-4-methyl-6H-pyrazolo[3,4-c]isothiazole-3-carbonitrile(1603826-50-1)

Safety Data

• Hazardous Substances Data: 1603826-50-1(Hazardous Substances Data)

Upstream product

• 75318-43-3 4,5-dichloro-1,2,3-dithiazolium chloride 
• 1134-82-3 5-amino-1-benzyl-3-methylpyrazole 

Relevant articles and documents

Reinvestigating the reaction of 1H-pyrazol-5-amines with 4,5-dichloro-1,2,3-dithiazolium chloride: A route to pyrazolo[3,4-c]isothiazoles and pyrazolo[3,4-d]thiazoles

The reaction of Appel salt 1 with 1H-pyrazol-5-amines 2 gives main products N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-1H-pyrazol-5-amines 3, and 6H-pyrazolo[3,4-c]isothiazole-3-carbonitriles 5, together with several minor side products. When the pyrazoles are N-1 methylated, the product ratio 3:5 can be modified by adjusting the pH of the reaction medium: acidic conditions favor formation of the dithiazolylidenes 3, while basic conditions favor formation of pyrazolo[3,4-c]isothiazoles 5. Furthermore, thermolysis of N-(4-chloro-5H-1,2,3- dithiazol-5-ylidene)-1H-pyrazol-5-amines 3 gives 1H-pyrazolo[3,4-d]thiazole-5- carbonitriles 4. Single crystal X-ray crystallography supports the structure of 4,6-dimethyl-6H-pyrazolo[3,4-c]isothiazole-3-carbonitrile (5a) and helps resolve a previous incorrect structural assignment of 1H-pyrazolo[3,4-d]thiazole-5- carbonitriles 4.