817-87-8

Basic information

• Product Name: Ethylazidoformate
• Synonyms: Ethylazidoformate
• CAS NO: 817-87-8
• Molecular Formula: C₃H₅N₃O₂
• Molecular Weight: 115.0907
• Mol File: 817-87-8.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 215.34°C (rough estimate)
• Appearance: /
• Density: 1.4923 (rough estimate)
• Refractive Index: 1.4500 (estimate)
• CAS DataBase Reference: Ethylazidoformate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethylazidoformate(817-87-8)
• EPA Substance Registry System: Ethylazidoformate(817-87-8)

Safety Data

• Hazardous Substances Data: 817-87-8(Hazardous Substances Data)

Usage

General Description

Ethylazidoformate, also known as ethyl N-azidoformate, is a chemical compound with the molecular formula C3H5N3O2. It is a colorless, highly explosive liquid with a slightly sweet odor. Ethylazidoformate is primarily used as a reagent in organic synthesis for the preparation of azides, a functional group that is commonly found in various pharmaceutical and agrochemical compounds. It is also used as a reagent in the preparation of carbamates, which are important in the pharmaceutical industry as precursors for the synthesis of a variety of drugs. However, ethylazidoformate is highly reactive and must be handled with extreme caution, as it can explode upon contact with certain metals, organic materials, or even light friction. Due to its hazardous nature, strict safety protocols must be followed in its handling and storage.

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 64-19-7 acetic acid 
• 4114-31-2 ethylhydrazine carboxylate 
• 623-33-6 glycine ethyl ester hydrochloride 
• 57-14-7 N,N-Dimethylhydrazine 
• 1972-28-7 diethylazodicarboxylate 

Downstream Products

• 51084-05-0 N'-phenyl-triazene carboxylic acid ethylester 
• 34106-68-8 3,3-dioxo-3λ⁶-thia-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester 
• 153718-64-0 2,3-dimethoxyphenylcarbamic acid ethyl ester 
• 106107-51-1 ethyl (3,4-dimethoxyphenyl)carbamate 
• 29329-11-1 Diaethyl 3,4-Dimethoxy-1,2-phenylendicarbamat 
• 70084-53-6 N-(1,1-Dimethyl-2-hydroxyethyl)urethan 
• 63767-49-7 isobutoxycarbamic acid ethyl ester 
• 1541-19-1 ethyl N-cyclohexylcarbamate 
• 26212-61-3 (2-ethoxy-5,5-diethyl-oxazol-4-ylidene)-p-tolyl-amine 
• 72006-07-6 Ethoxycarbonylamino-(2-hydroxy-phenyl)-acetic acid 
• 3206-31-3 tris(ethoxycarbonyl)amine 
• 1134-56-1 5-Phenyl-2-ethoxy-1,3,4-oxadiazole 
• 17437-51-3 N-(ethoxycarbonyl)triphenylphosphinimine 
• 70197-04-5 1-ethoxycarbonyl-2-phenylaziridine 

Relevant articles and documents

Contrasting behavior in azide pyrolyses: An investigation of the thermal decompositions of methyl azidoformate, ethyl azidoformate and 2-azido-N, N-dimethylacetamide by ultraviolet photoelectron spectroscopy and matrix isolation infrared spectroscopy

The thermal decompositions of methyl azidoformate (N3COOMe), ethyl azidoformate (N3COOEt) and 2-azido-N,N-dimethylacetamide (N3CH2-CONMe2) have been studied by matrix isolation infrared spectroscopy and real-time ultraviolet photoelectron spectroscopy. N2 appears as an initial pyrolysis product in all systems, and the principal interest lies in the fate of the accompanying organic fragment. For methyl azidoformate, four accompanying products were observed: HNCO, H2CO, CH2NH and CO2, and these are believed to arise as a result of two competing decomposition routes of a four-membered cyclic intermediate. Ethyl azidoformate pyrolysis yields four corresponding products: HNCO, MeCHO, MeCHNH and CO2, together with the five-membered-ring compound 2-oxazolidone. In contrast, the initial pyrolysis of 2-azido-N,N-dimethyl acetamide, yields the novel imine intermediate Me2NCOCH=NH, which subsequently decomposes into dimethyl formamide (HCONMe2), CO, Me2NH and HCN. This intermediate was detected by matrix isolation IR spectroscopy, and its identity confirmed both by a molecular orbital calculation of its IR spectrum, and by the temperature dependence and distribution of products in the PES and IR studies. Mechanisms are proposed for the formation and decomposition of all the products observed in these three systems, based on the experimental evidence and the results of supporting molecular orbital calculations.

Visible-Light-Induced Multicomponent Synthesis of γ-Amino Esters with Diazo Compounds

A visible-light-induced multicomponent reaction of ethyl diazoacetate, diarylamines, and styrene-type alkenes is described. This novel 1,2-difunctionalization of alkenes can be readily achieved under a simple operation and mild conditions, affording γ-amino esters as major products. The reaction proceeds through the generation of carbon-centered radicals from diazo compounds by a visible-light-promoted proton-coupled electron transfer (PCET) process. The carbon radicals then add to diverse alkenes, delivering new carbon radical species, and the final products are formed with N-centered radicals via a radical-radical coupling.

Copper(I)-Catalyzed Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Azidoformates and Aryl Terminal Alkynes

The copper(I)-catalyzed azide-alkyne cycloaddition reaction has been extensively studied and widely applied in organic synthesis. However, the formation of 1,2,3-triazoles with electron-deficient azide has been a challenging problem. In this report, we ha

Spin-selective generation of triplet nitrenes: Olefin aziridination through visible-light photosensitization of azidoformates

Azidoformates are interesting potential nitrene precursors, but their direct photochemical activation can result in competitive formation of aziridination and allylic amination products. Herein, we show that visible-light-activated transition-metal comple