10271-27-9

Basic information

• Product Name: ethyl [(1E)-3-(4-nitrophenyl)triaz-1-en-1-yl]acetate
• CAS NO: 10271-27-9
• Molecular Formula: C₁₀H₁₂N₄O₄
• Molecular Weight: 252.2267
• Mol File: 10271-27-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 362.7°C at 760 mmHg
• Flash Point: 173.2°C
• Density: 1.34g/cm³
• Vapor Pressure: 1.9E-05mmHg at 25°C
• Refractive Index: 1.586
• CAS DataBase Reference: ethyl [(1E)-3-(4-nitrophenyl)triaz-1-en-1-yl]acetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl [(1E)-3-(4-nitrophenyl)triaz-1-en-1-yl]acetate(10271-27-9)
• EPA Substance Registry System: ethyl [(1E)-3-(4-nitrophenyl)triaz-1-en-1-yl]acetate(10271-27-9)

Safety Data

• Hazardous Substances Data: 10271-27-9(Hazardous Substances Data)

Upstream product

• 623-33-6 glycine ethyl ester hydrochloride 
• 100-01-6 4-nitro-aniline 
• 100-05-0 4-nitrobenzenediazonium chloride 

Downstream Products

• 87604-99-7 1-(p-nitrophenyl)-5-acetoxy-1,2,3-triazole 
• 87604-95-3 1-(p-nitrophenyl)-5-hydroxy-1,2,3-triazole 
• 100-01-6 4-nitro-aniline 
• 623-73-4 diazoacetic acid ethyl ester 
• 144775-09-7 [3-(4-nitro-phenyl)-triazenyl]-acetic acid 

Relevant articles and documents

-

-

Open-chain nitrogen compounds. Part IV. Synthesis of 5-hydroxy-1,2,3-triazoles from 1-aryl-3-(ethoxycarbonylmethyl)triazenes: a new route to α-diazo-N-arylacetamides

A series of triazenes of type ArN=N-NH-CH2CO2Et, N-arylazoglycine ethyl esters, have been prepared by coupling the arene diazonium salt, ArN2+*X-, with ethyl glycinate, NH2CH2CO2Et; an electron-withdrawing substituent, e.g.NO2, CN, CO2R, and Cl, in the ortho or para position of the aryl group is essential for efficient coupling.The p-substituted arylazoglycine ethyl esters cyclize when treated with alcoholic potassium hydroxide to afford the potassium salts of the 1-aryl-5-hydroxy-1,2,3-triazoles, which can be obtained free by acidification of the potassium salt solution with acetic acid.Reaction of the potassium salts with acetic anhydride yields the 1-aryl-5-acetoxy-1,2,3-triazoles.The 5-hydroxytriazoles, when heated in ethanol, rearrange to α-diazoacetanilides, ArNH*COCHN2.The diazoamides can be obtained in low yield directly from the triazenes by prolonged refluxing in ethanol. o-Substituted aryltriazenes do not cyclize under the same conditions but fragment to the arylamine.