183739-73-3

Basic information

• Product Name: 1H-Pyrazole-4-carbonitrile, 3-amino-5-(3-nitrophenyl)-
• CAS NO: 183739-73-3
• Molecular Formula: C10H7N5O2
• Molecular Weight: 229.198
• Mol File: 183739-73-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1H-Pyrazole-4-carbonitrile, 3-amino-5-(3-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole-4-carbonitrile, 3-amino-5-(3-nitrophenyl)-(183739-73-3)
• EPA Substance Registry System: 1H-Pyrazole-4-carbonitrile, 3-amino-5-(3-nitrophenyl)-(183739-73-3)

Safety Data

• Hazardous Substances Data: 183739-73-3(Hazardous Substances Data)

Upstream product

• 90854-70-9 3-nitro-dithiobenzoic acid methyl ester 
• 183739-72-2 3-(3-nitrophenyl)-3-methylmercapto-2-cyano-acrylonitrile 
• 99-61-6 3-nitro-benzaldehyde 
• 109-77-3 malononitrile 
• 121-92-6 3-nitrobenzoic acid 
• 1188023-18-8 2-(methoxy(3-nitrophenyl)methylene)malononitrile 
• 1479642-36-8 C₁₀H₅N₃O₃ 
• 121-90-4 m-nitrobenzoic acid chloride 

Downstream Products

• 1187734-00-4 3-amino-5-(3-aminophenyl)-1H-pyrazole-4-carbonitrile 
• 1627744-36-8 C₁₀H₉N₅O₃ 
• 183738-69-4 4-(3-chloro-phenylamino)-3-(3-nitro-phenyl)-1H-pyrazolo[3,4-d]pyrimidine 

Relevant articles and documents

Novel biocompatible glucose-based deep eutectic solvent as recyclable medium and promoter for expedient multicomponent green synthesis of diverse three and four substituted pyrazole-4-carbonitrile derivatives

A novel biocompatible glucose-based deep eutectic solvent (DES) is reported for the first time in the multicomponent synthesis of diverse three and four substituted pyrazole-4-carbonitrile derivatives under catalyst-free condition without using any harmful organic solvent even for purification of the products. The desired products were obtained with high degree of diversity from the reaction of malononitrile, aromatic aldehydes and various hydrazine derivatives as nitrogen source at room temperature within short reaction times and good to excellent product yields. The deep eutectic solvent was also recycled and reused at least four times with only a slight loss of efficiency. A plausible mechanism was also proposed indicating the role of DES hydrogen bonding in the reaction promotion.

The conversion of isothiazoles into pyrazoles using hydrazine

The conversion of isothiazoles into pyrazoles on treatment with hydrazine is investigated. The influence of various C-3, C-4 and C-5 isothiazole substituents and some limitations of this ring transformation are examined. When the isothiazole C-3 substituent is a good nucleofuge, 3-aminopyrazoles are obtained. However, when the 3-substituent is not a leaving group it is retained in the pyrazole product. Treatment of 4-bromo-3-chloro-5-phenylisothiazole 56 or 3-chloro-4,5-diphenylisothiazole 57 with anhydrous hydrazine at ca. 200 °C for a few minutes gives the corresponding 3-hydrazinoisothiazoles 61 and 64 respectively in high yields; the stability of these new hydrazines is investigated. 5,5′-Diphenyl-3,3′-biisothiazole-4,4′-dicarbonitrile 78 reacts with hydrazine to give 5,5′-diphenyl-3,3′-bi(1H-pyrazole)-4,4′-dicarbonitrile 79. Methylhydrazine reacts with 3-chloro-5-phenylisothiazole-4-carbonitrile 1 to give 3-(1-methylhydrazino)-5-phenylisothiazole-4-carbonitrile 83 and 3-amino-1-methyl-5-phenylpyrazole-4-carbonitrile 84. All products are fully characterised and rational mechanisms for the isothiazole into pyrazole transformation are proposed.

Use of a pharmacophore model for the design of EGF-R tyrosine kinase inhibitors: 4-(Phenylamino)pyrazolo[3,4-d]pyrimidines

In the course of the random screening of a pool of CIBA chemicals, the two pyrazolopyrimidines 1 and 2 have been identified as fairly potent inhibitors of the EGF-R tyrosine kinase. Using a pharmacophore model for ATP- competitive inhibitors interacting w