28989-23-3

Basic information

• Product Name: 3-CHLORO-5-PHENYLISOTHIAZOLE-4-CARBONITRILE, 97
• Synonyms: 3-chloro-5-phenylisothiazole-4-carbonitrile;3-CHLORO-5-PHENYLISOTHIAZOLE-4-CARBONITRILE, 97;3-chloro-5-phenyl-1,2-thiazole-4-carbonitrile;3-chloro-5-phenyl-4-isothiazolecarbonitrile
• CAS NO: 28989-23-3
• Molecular Formula: C₁₀H₅ClN₂S
• Molecular Weight: 220.6781
• Mol File: 28989-23-3.mol

Chemical Properties

• Melting Point: 85℃
• Appearance: /
• CAS DataBase Reference: 3-CHLORO-5-PHENYLISOTHIAZOLE-4-CARBONITRILE, 97(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-5-PHENYLISOTHIAZOLE-4-CARBONITRILE, 97(28989-23-3)
• EPA Substance Registry System: 3-CHLORO-5-PHENYLISOTHIAZOLE-4-CARBONITRILE, 97(28989-23-3)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.; R36/37/38:Irritating to eyes, respiratory system
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36/37/39:Wear suitabl
• Hazardous Substances Data: 28989-23-3(Hazardous Substances Data)

Upstream product

• 2700-22-3 Benzylidenemalononitrile 
• 2120-82-3 3,5-dichloro-4-cyano isothiazole 
• 98-80-6 phenylboronic acid 
• 28557-00-8 phenylzinc chloride 
• 960-16-7 tributylphenylstannane 
• 100-52-7 benzaldehyde 
• 591-50-4 iodobenzene 
• 915395-41-4 3-chloroisothiazole-4-carbonitrile 

Downstream Products

• 223440-06-0 3-ethylsulfanyl-5-phenyl-isothiazole-4-carbonitrile 
• 221006-20-8 3-methylthio-5-phenyl-4-isothiazolecarbonitrile 
• 915395-63-0 3-(benzylamino)-5-phenylisothiazole-4-carbonitrile 
• 799279-49-5 3,3'-bis-(4-cyano-5-phenylisothiazole)disulfide 
• 915395-64-1 3,3'-methylenebis(sulfanediyl)bis(5-phenylisothiazole-4-carbonitrile) 
• 42754-61-0 3-amino-5-phenyl-1H-pyrazole-4-carbonitrile 
• 36778-07-1 3-hydroxy-5-phenylisothiazole-4-carbonitrile 
• 1732-53-2 3-methyl-5-phenyl-isothiazole-4-carboxylic acid 
• 1732-52-1 4-Cyan-3-methyl-5-phenylisothiazol 
• 1187734-06-0 (1-methylhydrazinyl)-5-phenylisothiazole-4-carbonitrile 
• 21762-93-6 3-amino-1-methyl-5-phenyl-1H-pyrazole-4-carbonitrile 

Relevant articles and documents

CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF

Disclosed herein are small molecule calpain modulator compositions, pharmaceutical compositions, the use and preparation thereof.

Isothiazole derivatives as GPR120 agonists for the treatment of type II diabetes

Disclosed are compounds, compositions and methods for treating of disorders that are affected by the modulation of the GPR120 receptor. Such compounds are represented by Formula (I) as follows: wherein R1, G, and Q are defined herein.

ISOTHIAZOLE DERIVATIVES AS GPR120 AGONISTS FOR THE TREATMENT OF TYPE II DIABETES

Disclosed are compounds, compositions and methods for treating of disorders that are affected by the modulation of the GPR120 receptor. Such compounds are represented by Formula (I) as follows: wherein R1, G, and Q are defined herein.

GPR120 AGONISTS FOR THE TREATMENT OF TYPE II DIABETES

Disclosed are compounds, compositions and methods for treating of disorders that are affected by the modulation of the GPR120 receptor. Such compounds are represented by Formula (I) and Formula (II) as follows: wherein Y, R1, G, and Q are defined herein; and wherein R11, R21, R41, RB1 and G1, are defined herein.

Silver-mediated palladium-catalyzed direct C-H arylation of 3-bromoisothiazole-4-carbonitrile

Silver(I) fluoride-mediated Pd-catalyzed C-H direct arylation/ heteroarylation of 3-bromoisothiazole-4-carbonitrile (1a) gives twenty-four 5-aryl/heteroaryl-3-bromoisothiazole-4-carbonitriles. The reaction was partially optimized with respect to catalyst, ligand, and base. During this study 3,3′-dibromo-5,5′-biisothiazole-4,4′-dicarbonitrile (3a) was isolated as a byproduct and subsequently prepared via the silver-mediated Pd-catalyzed oxidative dimerization of 3-bromoisothiazole-4-carbonitrile in 67% yield. The analogous phenylation and oxidative dimerization of 3-chloroisothiazole-4-carbonitrile (1b) gave 3-chloro-5-phenylisothiazole-4- carbonitrile (4) and 3,3′-dichloro-5,5′-biisothiazole-4,4′- dicarbonitrile (3b) in 96% and 69% yields, respectively.

New regiospecific isothiazole C-C coupling chemistry

Regioselective palladium catalysed coupling reactions are achieved in good to high yields, starting from either 3,5-dichloro- or 3,5-dibromoisothiazole-4-carbonitriles 1 and 2, providing 3-halo-5-(hetero/aryl, alkenyl and alkynyl)isothiazoles 3, 4, 6-9 fr

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.

Synthesis and antiviral activity of a new series of 4-isothiazolecarbonitriles

A series of 4-isothiazolecarbonitriles was synthesized and screened for in vitro antiviral activity. The effect of various substituents on the phenyl ring, as well as the substitution of the phenyl for other aromatic and heteroaromatic rings, was examined