1956-97-4

Basic information

• Product Name: Benzenediazonium, 2-chloro-, tetrafluoroborate(1-)
• CAS NO: 1956-97-4
• Molecular Formula: C6H4ClN2.BF4
• Molecular Weight: 226.369
• Mol File: 1956-97-4.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: Benzenediazonium, 2-chloro-, tetrafluoroborate(1-)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenediazonium, 2-chloro-, tetrafluoroborate(1-)(1956-97-4)
• EPA Substance Registry System: Benzenediazonium, 2-chloro-, tetrafluoroborate(1-)(1956-97-4)

Safety Data

• Hazardous Substances Data: 1956-97-4(Hazardous Substances Data)

Usage

General Description

Benzenediazonium, 2-chloro-, tetrafluoroborate(1-) is a chemical compound commonly used in organic synthesis as a source of aryl cations. It is prepared by the reaction of aniline with nitrous acid, followed by treatment with tetrafluoroboric acid. Benzenediazonium, 2-chloro-, tetrafluoroborate(1-) is a stable, crystalline salt that is highly reactive and can be used in the Sandmeyer reaction to introduce various functional groups onto the benzene ring. It is also used as a precursor in the synthesis of dyes, pharmaceuticals, and other organic compounds. However, it must be handled with caution due to its potential to decompose explosively under certain conditions.

Upstream product

• 95-51-2 o-chloroaniline 
• 13755-29-8 sodium tetrafluoroborate 

Downstream Products

• 141320-15-2 (2-Chloro-phenyl)-isopropyl-diazene 
• 141320-16-3 Butyl-(2-chloro-phenyl)-diazene 
• 84451-23-0 2-chloro-tellurophenetole 
• 141320-14-1 (2-Chloro-phenyl)-cyclohexyl-diazene 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 38793-82-7 1-(2-Chlorophenyl)cyclopentene 
• 78135-02-1 1-Chloro-2-cyclopent-2-enyl-benzene 
• 348-51-6 1-chloro-2-fluorobenzene 
• 24966-41-4 S-<2-Chlor-phenyl>-isothioharnstoff 
• 13659-07-9 1,3-Diphenyl-2-<2-chlor-phenyl>-isothioharnstoff 
• 60095-84-3 (2-chlorophenyl)azo 4-methylphenyl sulfone 
• 10449-07-7 (2-chlorophenyl)hydrazine 
• 88-73-3 2-Chloronitrobenzene 
• 49795-06-4 (E)-bis(2-chlorophenyl)diazene 

Relevant articles and documents

Aqueous and Visible-Light-Promoted C-H (Hetero)arylation of Uracil Derivatives with Diazoniums

Direct C5 (hetero)arylation of uracil and uridine substrates with (hetero)aryl diazonium salts under photoredox catalysis with blue light was reported. The coupling proceeds efficiently with diazonium salts and heterocycles in good functional group tolerance at room temperature in aqueous solution without transition-metal components. A plausible radical mechanism has been proposed.

Comparison of the Thermal Stabilities of Diazonium Salts and Their Corresponding Triazenes

A range of diazonium salts and their corresponding triazenes have been prepared in order to directly compare their relative thermal stabilities (via initial decomposition temperature) from differential scanning calorimetry (DSC) data. A structure-stability relationship has been explored to investigate trends in stability, depending on the aromatic substituent and the structure of the secondary amine component of the diazonium salts and triazenes. All of the triazenes investigated show significantly greater stability (many are stable above 200 °C) compared with the corresponding diazonium salts, which show varying stabilities.

Discovery and structure-activity relationship studies of 1-aryl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as potent dual inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1) and trytophan 2,3-dioxygenase (TDO)

Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO), which mediate kynurenine pathway of tryptophan degradation, have emerged as potential new targets in immunotherapy for treatment of cancer because of their critical role in immunosuppression in the tumor microenvironment. In this investigation, we report the structural optimization and structure-activity relationship studies of 1-phenyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as a new class of IDO1/TDO dual inhibitors. Among all the obtained dual inhibitors, 1-(3-chloro-4-fluorophenyl)-6-fluoro-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione (38) displayed the most potent IDO1 and TDO inhibitory activities with IC50 (half-maximal inhibitory concentration) values of 5 nM for IDO1 and 4 nM for TDO. It turned out that compound 38 was not a PAINS compound. Compound 38 could efficiently inhibit the biofunction of IDO1 and TDO in intact cells. In LL2 (Lewis lung cancer) and Hepa1-6 (hepatic carcinoma) allograft mouse models, this compound also showed considerable in vivo anti-tumor activity and no obvious toxicity was observed. Therefore, 38 could be a good lead compound for cancer immunotherapy and deserving further investigation.