144993-01-1

Basic information

• Product Name: 3-diazo-5-(p-tolyl)-3H-pyrazole
• Synonyms: 3-diazo-5-(p-tolyl)-3H-pyrazole
• CAS NO: 144993-01-1
• Molecular Weight: 184.2
• Mol File: 144993-01-1.mol

Chemical Properties

• CAS DataBase Reference: 3-diazo-5-(p-tolyl)-3H-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-diazo-5-(p-tolyl)-3H-pyrazole(144993-01-1)
• EPA Substance Registry System: 3-diazo-5-(p-tolyl)-3H-pyrazole(144993-01-1)

Safety Data

• Hazardous Substances Data: 144993-01-1(Hazardous Substances Data)

Upstream product

• 151293-15-1 5-amino-3-(4-methylphenyl)-1H-pyrazole 

Downstream Products

• 1448041-57-3 (Z)-ethyl 7-(p-tolyl)-4H-pyrazolo[5,1-d][1,2,3,5]thiatriazin-4-ylidenecarbamate 
• 1448041-58-4 (Z)-N-(7-(p-tolyl)-4H-pyrazolo[5,1-d][1,2,3,5]thiatriazin-4-ylidene)benzamide 
• 1448041-59-5 (Z)-2,3,4,5-tetrafluoro-N-(7-p-tolyl-4H-pyrazolo[5,1-d][1,2,3,5]thiatriazin-4-ylidene)-benzamide 

Relevant articles and documents

Synthesis and properties of 5-aryl-3-diazo-3H-pyrazoles and 3-aryl-1H-pyrazole-5-diazonium salts. Preparation and cytolytic activity studies of 2-arylpyrazolo-[5,1-c][1,2,4]benzotriazines

[Figure not available: see fulltext.] A comparative analysis of physicochemical properties and reactivity of 3-aryl-1H-pyrazole-5-diazonium tetrafluoroborates and 5-aryl-3-diazo-3H-pyrazoles in azo coupling reactions is presented. It is shown that diazonium salts have higher reactivity compared to the respective 3-diazopyrazoles, which is in agreement with their physicochemical properties. Heterocyclization of the synthesized azo compounds provided 2-arylpyrazolo[5,1-c][1,2,4]benzotriazines, which were screened for antitumor activity against human uterine endothelium cancer cells (HeLa cell line) and human skin fibroblasts using the MTT assay and flow cytometry. It was found that all of the tested compounds exhibited moderate to high cytotoxic activity. The best results were obtained with 6,8-dimethoxy-2-phenylpyrazolo-[5,1-c][1,2,4]benzotriazine.

Synthesis of new azolo[5,1-d][1,2,3,5]tetrazin-4-ones–analogs of antitumor agent temozolomide

Reactivity of 5-diazoimidazoles and 5-diazopyrazoles in the reactions with alkyland aryl isocyanates was studied. A number of new imidazo-and pyrazolo[5,1-d][1,2,3,5]tetrazin-4 ones were synthesized, which are analogs of temozolomide. It was shown that diazoazoles do not react with isothiocyanates under similar conditions.

Synthesis and structure of new imidazo- and pyrazolo[5,1-d][1,2,3,5] thiatriazines based on the reaction of diazoazoles with acyl isothiocyanates controlled by Sa?O interaction

5-Diazoimidazoles and 5-diazopyrazoles have been shown to react with acyl isothiocyanates yielding the imidazo- and pyrazolo[5,1-d][1,2,3,5]thiatriazines stabilized by a nonbonded Sa?O interaction. In contrast to acyl isothiocyanates, alkyl-, aryl-, and arylsulfonyl isothiocyanates do not react with 5-diazoazoles. The nature and the strength of stabilizing intramolecular interaction between non-bonded S and O atoms have been studied by X-ray analysis for mono crystals and DFT calculations for selected azolo[5,1-d][1,2,3,5] thiatriazines. The interaction was described in terms of Weinhold covalence ratio factors, NBO, and AIM schemes. The reaction discovered was used to develop an efficient approach toward the new 8-substituted 4-ethoxycarbonylimino-4- benzoyl- and 4-(3,4,5,6-tetrafluorobenzoyl)iminoimidazo(pyrazolo)[5,1-d][1,2,3, 5]thiatriazines.