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

• 138291-34-6 3-[1-(2-Chloro-phenyl)-meth-(E)-ylidene]-2,2-dimethyl-bicyclo[2.2.1]heptane 
• 79827-98-8 (2-chlorobenzenediazosulfonyl)benzene 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 95-49-8 2-methylchlorobenzene 
• 348-51-6 1-chloro-2-fluorobenzene 
• 6320-03-2 2-chlorothiphenol 
• 13659-07-9 1,3-Diphenyl-2-<2-chlor-phenyl>-isothioharnstoff 
• 1332285-06-9 C₁₂H₁₅ClO₂ 
• 1612831-65-8 (E)-methyl 3-(2-chlorophenyl)-2-(hydroxyimino)propanoate 
• 113961-63-0 methyl 2-amino-3-(2-chlorophenyl)propanoate 
• 2905-23-9 2-chlorophenylsulfonyl chloride 
• 2051-60-7 2-chloro-1,1'-biphenyl 

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.

Highly Efficient Synthesis of Hindered 3-Azoindoles via Metal-Free C-H Functionalization of Indoles

Although 3-azoindoles have recently emerged as an appealing family of photoswitch molecules, the synthesis of such compounds has been poorly covered in the literature. Herein a high-yielding and operationally simple protocol is reported allowing the synthesis of 3-azoindoles, featuring important steric hindrance around the azo motif. Remarkably, this C-H coupling is characterized by excellent atom economy and occurs under metal-free conditions, at room temperature, and within few minutes, delivering the expected products in excellent yields (quantitatively in most of the cases). Accordingly, a library of new molecules, with potential applications as photochromic compounds, is prepared.

Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: Synthesis of: N -arylpyrazoles

A general method for the synthesis of structurally diverse N-arylpyrazoles from readily available cyclopropanols and aryldiazonium salts is disclosed. The reaction was conducted at room temperature within minutes with a broad substrate scope and excellent regioselectivity.