16722-99-9

Basic information

• Product Name: Benzene, (2-azidoethenyl)-
• CAS NO: 16722-99-9
• Molecular Formula: C8H7N3
• Molecular Weight: 145.164
• Mol File: 16722-99-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzene, (2-azidoethenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (2-azidoethenyl)-(16722-99-9)
• EPA Substance Registry System: Benzene, (2-azidoethenyl)-(16722-99-9)

Safety Data

• Hazardous Substances Data: 16722-99-9(Hazardous Substances Data)

Upstream product

• 51443-08-4 C₂₆H₂₄N₂P⁽¹⁺⁾*F^(1-) 
• 4363-35-3 Dihydroxy-styryl-boran 
• 103-64-0 bromostyrene 
• 621-82-9 Cinnamic acid 
• 100-42-5 styrene 
• 140-10-3 (E)-3-phenylacrylic acid 

Downstream Products

• 3652-48-0 ethyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate 
• 13219-97-1 4-acetyl-5-methyl-2-phenylpyrrole 
• 18756-04-2 1-styryl-4-phenyl-1,2,3-triazole 
• 7654-06-0 3-phenyl-2H-azirine 
• 927384-80-3 C₁₆H₁₃N₃ 
• 1293362-65-8 C₂₁H₂₃N₃O₆ 
• 1722-84-5 (E)-N-styrylacetamide 

Relevant articles and documents

Nucleophilic Iron Complexes in Proton-Transfer Catalysis: An Iron-Catalyzed Dimroth Cyclocondensation

The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) is an active catalyst in C?H-amination but also in proton-transfer catalysis. Herein, we describe the successful use of this complex as a proton-transfer catalyst in the cyclocondensation reaction between azides and ketones to the corresponding 1,2,3-triazoles. Cross-experiments indicate that the proton-transfer catalysis is significantly faster than the nitrene-transfer catalysis, which would lead to the C?H amination product. An example of a successful sequential Dimroth triazole–indoline synthesis to the corresponding triazole-substituted indolines is presented.

Synthesis of 2,3,4-trisubstituted pyrroles via a facile reaction of vinyl azides and tosylmethyl isocyanide

A facile synthesis of polysubstituted pyrroles from tosylmethyl isocyanide (TOSMIC) and readily synthesized vinyl azides was developed. The reaction proceeded under mild conditions in the presence of base. 2-Tosyl-substituted pyrroles were obtained in moderate to good isolated yields. Additionally, a base-initiated one-pot pyrrole synthesis also was developed using carboxaldehydes, ethyl 2-azidoacetate, and TOSMIC.

Synthesis of polysubstituted N-H pyrroles from vinyl azides and 1,3-dicarbonyl compounds

(Chemical Equation Presented) Two synthetic methods for tetra- and trisubstituted N-H pyrroles are presented: (i) the thermal pyrrole formation by the reaction of vinyl azides with 1,3-dicarbonyl compounds via the 1,2-addition of 1,3-dicarbonyl compounds to 2H-azirine intermediates generated in situ from vinyl azides; (ii) the Cu(II)-catalyzed synthesis of pyrroles from α-ethoxycarbonyl vinyl azides and ethyl acetoacetate through the 1,4-addition reaction of the acetoacetate to the vinyl azides. By applying these two methods, regioisomeric pyrroles can be prepared selectively starting from the same vinyl azides.