28989-24-4

Basic information

• Product Name: 4-Isothiazolecarbonitrile, 3-chloro-5-(4-chlorophenyl)-
• CAS NO: 28989-24-4
• Molecular Formula: C10H4Cl2N2S
• Molecular Weight: 255.127
• Mol File: 28989-24-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-Isothiazolecarbonitrile, 3-chloro-5-(4-chlorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Isothiazolecarbonitrile, 3-chloro-5-(4-chlorophenyl)-(28989-24-4)
• EPA Substance Registry System: 4-Isothiazolecarbonitrile, 3-chloro-5-(4-chlorophenyl)-(28989-24-4)

Safety Data

• Hazardous Substances Data: 28989-24-4(Hazardous Substances Data)

Upstream product

• 1679-18-1 4-Chlorophenylboronic acid 
• 2120-82-3 3,5-dichloro-4-cyano isothiazole 
• 1867-38-5 4-chlorobenzylidenemalonodinitrile 

Downstream Products

• 42754-62-1 3-amino-5-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile 

Relevant articles and documents

Regiospecific Suzuki coupling of 3,5-dichloroisothiazole-4-carbonitrile

3,5-Dichloroisothiazole-4-carbonitrile 1 reacts with aryl- and methylboronic acids to give in high yields the 3-chloro-5-(aryl and methyl)-isothiazole-4-carbonitrile 2 regiospecifically. The reaction was optimized with respect to base, phase transfer agent and palladium catalyst. Suzuki coupling at C-5 was also achieved in high yield using potassium phenyltrifluoroborate. The regiospecificity of either coupling method is maintained with 3,5-dibromoisothiazole-4-carbonitrile 4 to give exclusively 3-bromo-5-phenylisothiazole-4-carbonitrile 5. Suzuki cross-coupling conditions applied to 3-chloro-5-phenylisothiazole-4-carbonitrile 2a gave 3-phenoxy-5-phenylisothiazole-4-carbonitrile 6, which was prepared independently, and not the 3-phenyl derivative. All isothiazole products were fully characterized.