31469-89-3

Basic information

• Product Name: 4-azido-2,3,5,6-tetrafluorobenzonitrile
• Synonyms: 4-azido-2,3,5,6-tetrafluorobenzonitrile
• CAS NO: 31469-89-3
• Molecular Weight: 216.097
• Mol File: 31469-89-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4-azido-2,3,5,6-tetrafluorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-azido-2,3,5,6-tetrafluorobenzonitrile(31469-89-3)
• EPA Substance Registry System: 4-azido-2,3,5,6-tetrafluorobenzonitrile(31469-89-3)

Safety Data

• Hazardous Substances Data: 31469-89-3(Hazardous Substances Data)

Upstream product

• 773-82-0 Pentafluorobenzonitrile 
• 17823-43-7 Methyl 4-cyano-2,3,5,6-tetrafluorobenzoate 

Downstream Products

• 17823-38-0 4-amino-2,3,5,6-tetrafluorobenzonitrile 
• 74632-44-3 4,4'-dicyanoperfluoroazobenzene 
• 913261-93-5 RuCl₂(CH₃C₆H₄CH(CH₃)2)(C₆H₅PC₄H₇P(C₆H₅)2NC₆F₄CN) 
• 653-22-5 1-Acetylamino-2,3,4,5,6-pentafluorobenzen 

Relevant articles and documents

Synthesis of nitrophenyl and fluorophenyl azides and diazides by SNAr under phase-transfer or microwave irradiation: Fast and mild methodologies to prepare photoaffinity labeling, crosslinking, and click chemistry reagents

Two fast and mild methodologies to prepare nitrophenyl and fluorophenyl azides are presented. These aryl azides are extensively used as crosslinking, photoaffinity labeling, and click chemistry reagents. Substituted aryl azides are prepared by performing a SNAr substitution on halogenated benzenes with a phase-transfer catalyst (PTC) such as tetraethylammonium tetrafluoroborate (TEATFB), the reaction proceeds in several hours under rather mild temperatures (25°C to 70°C). Furthermore, aryl azides are also prepared within minutes under microwave irradiation at slightly higher temperatures (50°C to 70°C). These procedures could be applied in the preparation of other aryl azides. In the case of substituted pentafluoro benzene (pF), the type of products obtained in each reaction depends on the amount of sodium azide and the strength and position of electron-withdrawing substituents (COH, COR, COOR, CN, NO2, or F). A discussion on the mechanisms and the products obtained in these SNAr reactions is presented.

N, N -diethylurea-catalyzed amidation between electron-deficient aryl azides and phenylacetaldehydes

Urea structures, of which N,N-diethylurea (DEU) proved to be the most efficient, were discovered to catalyze amidation reactions between electron-deficient aryl azides and phenylacetaldehydes. Experimental data support 1,3-dipolar cycloaddition between DEU-activated enols and electrophilic phenyl azides, especially perfluoroaryl azides, followed by rearrangement of the triazoline intermediate. The activation of the aldehyde under near-neutral conditions was of special importance in inhibiting dehydration/aromatization of the triazoline intermediate, thus promoting the rearrangement to form aryl amides.

Highly selective synthesis of 1-polyfluoroaryl-1,2,3-triazoles via a one-pot three-component reaction

A series of 1-polyfluoroaryl-1,2,3-triazoles were synthesized in moderate to good yields by an efficient copper-catalyzed one-pot three-component reaction of polyfluoroarenes, sodium azide, and terminal alkynes. The method involves a polyfluoroarylated azide intermediate produced in situ by the selective CF bond cleavage of polyfluoroarene with sodium azide.