Ethyl azidoformate

Base Information

• Chemical Name: Ethyl azidoformate
• CAS No.: 817-87-8
• Molecular Formula: C₃H₅N₃O₂
• Molecular Weight: 115.092
• DSSTox Substance ID: DTXSID30473667
• Nikkaji Number: J37.404K
• Wikidata: Q82303241
• Mol file: 817-87-8.mol

Synonyms:ETHYL AZIDOFORMATE;Ethyl N-diazocarbamate;817-87-8;azido(ethoxy)methanone;ethyl carbonazidate;DTXSID30473667;HZAHPOBLARATTK-UHFFFAOYSA-N;EN300-128333;A840196

Chemical Property of Ethyl azidoformate

Chemical Property:

• Refractive Index: 1.4500 (estimate)
• Boiling Point: 215.34°C (rough estimate)
• PSA: 76.05000
• Density: 1.4923 (rough estimate)
• LogP: 0.90596
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 115.038176411
• Heavy Atom Count: 8
• Complexity: 127

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s): 3
• Hazard Codes: 3

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)N=[N+]=[N-]

Technology Process of Ethyl azidoformate

There total 7 articles about Ethyl azidoformate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

chloroformic acid ethyl ester (541-41-3) → ethyl azidocarbonate (817-87-8)

Guidance literature:

With sodium azide; In diethyl ether; water; at 20 ℃; Cooling with ice;

DOI:10.1016/j.tetlet.2013.07.135

Reference yield:

N,N-Dimethylhydrazine (57-14-7) + diethylazodicarboxylate (1972-28-7,218603-74-8) → ethyl N,N-dimethylcarbamate (687-48-9) + Tetramethyltetrazon (6130-87-6) + ethyl azidocarbonate (817-87-8) + diethyl hydrazodicarboxylate (4114-28-7)

Guidance literature:

In tetrachloromethane; for 0.25h; Mechanism; Product distribution; Ambient temperature; diethyl azodicarboxylate was added to hydrazine derivate; using also two other hydrazine derivates;

Reference yield:

glycine ethyl ester hydrochloride (623-33-6) → ethyl azidocarbonate (817-87-8)

Guidance literature:

With sodium nitrite; In dichloromethane; water; at 18 - 20 ℃;

DOI:10.1021/acs.orglett.1c02071

upstream raw materials:

chloroformic acid ethyl ester

ethylhydrazine carboxylate

N,N-Dimethylhydrazine

diethylazodicarboxylate

Downstream raw materials:

N'-phenyl-triazene carboxylic acid ethylester

3,3-dioxo-3λ⁶-thia-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

(2,4-diphenyl-2H-[¹⁵N]isothiazol-5-ylidene)-carbamic acid ethyl ester

N-(1,1-Dimethyl-2-hydroxyethyl)urethan

Refernces

Asymmetric formation of C - N bonds in chiral enol ethers

10.1016/S0040-4020(01)86538-8

The research focuses on the asymmetric formation of C-N bonds in chiral enol ethers using (ethoxycarbonyl)methylene (EtO2CN2) or ethyl azidoformate (EtO2CN3) as reagents. The purpose of the study was to achieve a stereospecific introduction of an amino function by methylene addition to enol ethers containing a suitable chiral auxiliary. The researchers reported that the reaction of EtO2CN3 with chiral enol ethers at 120°C resulted in the formation of acetals of 2-(ethoxycarbonylammo)cyclohexanone with minor traces of amino ketone, except in one case where the amino ketone was the only detectable product. By employing ethyl N-{[(4-nitrophenyl)sulphonyl]oxy}carbamate at room temperature, they were able to directly obtain the desired amino ketone with high stereoselectivity. The study concluded that the room temperature amination reaction is a highly stereoselective process on chiral enol ethers using reactive reagents. Key chemicals used in the process include cyclohexanone, chiral 1,2-diols, triflic anhydride (TfOTMS), ethyl N-{[(4-nitrophenyl)sulphonyl]oxy}carbamate, and triethylamine, along with various enol ethers and acetals prepared from these starting materials.