70135-28-3

Basic information

• Product Name: Benzonitrile, 4-(diazomethyl)-
• CAS NO: 70135-28-3
• Molecular Formula: C8H5N3
• Molecular Weight: 143.148
• Mol File: 70135-28-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4-(diazomethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-(diazomethyl)-(70135-28-3)
• EPA Substance Registry System: Benzonitrile, 4-(diazomethyl)-(70135-28-3)

Safety Data

• Hazardous Substances Data: 70135-28-3(Hazardous Substances Data)

Upstream product

• 87829-00-3 4-(hydrazonomethyl)benzonitrile 
• 105-07-7 4-cyanobenzaldehyde 
• 41780-79-4 N'-(4-cyanobenzylidene)-4-methylbenzenesulfonohydrazide 

Downstream Products

• 121829-30-9 4-((1S,4S,5R,6R,7S)-6-Chloro-7-methylsulfanyl-2,3-diaza-bicyclo[3.2.0]hept-2-en-4-yl)-benzonitrile 
• 121829-29-6 4-((1S,4S,5R,6R,7S)-7-Chloro-6-methylsulfanyl-2,3-diaza-bicyclo[3.2.0]hept-2-en-4-yl)-benzonitrile 
• 121829-43-4 4-((1S,4S,5R,6R,7S)-6,7-Bis-methylsulfanyl-2,3-diaza-bicyclo[3.2.0]hept-2-en-4-yl)-benzonitrile 
• 874-89-5 4-Cyanobenzyl alcohol 
• 16473-21-5 1-cyano-4-(fluoromethyl)benzene 
• 88584-52-5 4,4'-(oxydimethylene)dibenzonitrile 
• 1007090-52-9 N-(4-cyanophenyl)-2-methyl-2-phenylaziridine 
• 29903-10-4 4,4'-(2-oxopropane-1,3-diyl)dibenzonitrile 
• 1276664-82-4 p-(exo-6-bicyclo[3.1.0]hexyl)valerophenone 
• 1276635-01-8 p-(endo-6-bicyclo[3.1.0]hexyl)valerophenone 

Relevant articles and documents

Continuous Flow Synthesis and Purification of Aryldiazomethanes through Hydrazone Fragmentation

Electron-rich diazo compounds, such as aryldiazomethanes, are powerful reagents for the synthesis of complex structures, but the risks associated with their toxicity and instability often limit their use. Flow chemistry techniques make these issues avoidable, as the hazardous intermediate can be used as it is produced, avoiding accumulation and handling. Unfortunately, the produced stream is often contaminated with other reagents and by-products, making it incompatible with many applications, especially in catalysis. Herein is reported a metal-free continuous flow method for the production of aryldiazomethane solutions in a non-coordinating solvent from easily prepared, bench-stable sulfonylhydrazones. All by-products are removed by an in-line aqueous wash, leaving a clean, base-free diazo stream. Three successful sensitive metal-catalyzed transformations demonstrated the value of the method.

A Versatile Room-Temperature Route to Di- and Trisubstituted Allenes Using Flow-Generated Diazo Compounds

A copper-catalyzed coupling reaction between flow-generated unstabilized diazo compounds and terminal alkynes provides di- and trisubstituted allenes. This extremely mild and rapid transformation is highly tolerant of several functional groups. Well tolerated: A mild copper-catalyzed coupling reaction between unstabilized diazo compounds (generated in flow) and terminal alkynes is reported. The method provides di- and trisubstituted allenes with high functional-group tolerance.

THE SYNTHESIS OF ARYL DIAZOMETHANES

A convenient and rapid method for preparing aryldiazomethanes from the related tosylhydrazones employing phase transfer catalysis with hydrocarbon solvents in good to excellent yields has been developed.