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:

98%Min ^*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:

1-Ethoxycarbonylimino-2-propyloxycarbonylimino-1,2-diphenyl-ethan

2-(4-chlorophenyl)-5-ethoxy-1,3,4-oxadiazole

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

ethyl N-cyclohexylcarbamate

Refernces

• 1、 Belloli et al.. "". . p. 1857. Retrieved 1972.
• 2、 Baykal, Aslihan,Zhang, Dihan,Knelles, Jakob,Alt, Isabel T.,Plietker, Bernd. "Nucleophilic Iron Complexes in Proton-Transfer Catalysis: An Iron-Catalyzed Dimroth Cyclocondensation". supporting information. p. 3003 - 3010. Retrieved 2019/08/21.
• 3、 Das, Debapratim,Samanta, Rajarshi. "Iridium(III)-Catalyzed Regiocontrolled Direct Amidation of Isoquinolones and Pyridones". supporting information. p. 379 - 384. Retrieved 2017/12/26.