53422-48-3

Upstream product

• 42059-30-3 1-azido-2-iodoethane 
• 1517-05-1 2-azidoethanol 
• 80-41-1 2-chloroethyl tosylate 

Downstream Products

• 199276-69-2 (4-azidobut-1-yn-1-yl)benzene 
• 130231-90-2 4-(β-chloroethyl)-5-picrylimino-1,2,3,4-thiatriazoline 
• 75394-71-7 1-(2-chloroethyl)-5-benzoyl-4-(2-ethyl-5-tetrazolyl)-1,2,3-triazole 
• 75-05-8 acetonitrile 
• 70520-59-1 [1-(2-chloro-ethyl)-1H-[1,2,3]triazol-4-yl]-phenyl-methanone 
• 738558-20-8 3-benzyl-3-(3-carboxypropanoyl)-1-(2-chloroethyl)triazene 
• 6099-88-3 2-Chloroethyl isothiocyanate 
• 70501-65-4 C,C'-diphenyl-C,C'-[1-(2-chloro-ethyl)-1H-[1,2,3]triazole-4,5-diyl]-bis-methanone 

Relevant academic research and scientific papers

Gas Phase Reactions, 58. β-Chloroethyl Azide: HCl Elimination and Pyrolysis

The HCl elimination from β-cloroethyl azide (1-azido-2-chloroethane) over potassium tert.butanolate at 350 K in a low pressure flow system is optimized using PE spectroscopic real-time gas analysis.The highly explosive vinyl azide formed can be purified by cool-trapping the by-products.Its subsequent and virtually hazard-free pyrolysis yields 2H-azirine, which can be isolated at temperatures below 240 K.In contrast, the direct pyrolysis of β-chloroethyl azide requires temperatures above 710 K and results in a simultaneous split-off of both HCl and N2, yielding acetonitrile as the main thermolysis product.No intermediates such as β-chloroethanimine or ketenimine are observed, a result which is interpreted in terms of chemical activation. - Keywords: β-Chloroethyl Azide, Vinyl Azide, Ketene Imine, 2H-Azirine, Gas Phase Dehydrochlorination

GAS-PHASE REACTIONS. 36. PYROLYSIS OF VINYL AZIDE.

The gas-phase pyrolyses of vinyl azide as well as of 1H-1,2,3-triazole have been investigated by means of PE spectroscopy. In accordance with predictions from MNDO hypersurface studies, vinyl azide in its lowest thermal decomposition channel splits off nitrogen to yield predominantly 2H-azirine as identified by the PE spectrum of the cool-trapped compound, which at higher temperatures rearranges to the most stable C//2H//3N isomer, acetonitrile. The experimental observations and the quantum chemical calculations both indicate that among those reaction pathways, which can readily be characterized by a suitably selected pair of reaction coordinates from the 12-dimensional hyperspace for the C//2H//3N moiety, synchronous nitrogen extrusion-azirine ring formation is the energetically most favorable one.