tert-Butyl azidoformate

Base Information

• Chemical Name: tert-Butyl azidoformate
• CAS No.: 1070-19-5
• Deprecated CAS: 51514-26-2,69109-90-6,69109-90-6
• Molecular Formula: C5H9 N3 O2
• Molecular Weight: 143.145
• Hs Code.: 2927000090
• European Community (EC) Number: 213-972-8
• NSC Number: 95410
• DSSTox Substance ID: DTXSID1061449
• Nikkaji Number: J25.572F
• Mol file: 1070-19-5.mol

Synonyms:tert-Butyl azidoformate;1070-19-5;tert-Butoxycarbonyl azide;tert-Butyloxycarbonyl azide;azido(tert-butoxy)methanone;t-butyl azidoformate;tert-butyl carbonazidate;tert-butyl (NE)-N-diazocarbamate;CARBONAZIDIC ACID, 1,1-DIMETHYLETHYL ESTER;EINECS 213-972-8;NSC 95410;Formic acid, azido-, tert-butyl ester;tert-butyl N-diazocarbamate;t-butoxycarbonylazide;BOC-azide;t-butylazidoformate;t-butyl carbonazidate;tert-butylazidoformate;tertbutoxycarbonylazide;t-butoxycarbonyl azide;Boc-N3;t-butoxylcarbonyl azide;tert-butoxycarbonylazide;tert.butoxycarbonylazide;tertbutoxycarbonyl azide;Azido tert-butoxymethanone;tert.-butoxycarbonyl azide;1,1-Dimethylethyl azidoformate;DTXSID1061449;1,1-dimethylethoxy carbonylazide;NSC95410;NSC-95410;tert-Butoxycarbonyl azide [Forbidden];AKOS006229511;Carbonazidic acid,1-dimethylethyl ester;N-diazo-carbamic acid tert-butyl ester;A801554

Chemical Property of tert-Butyl azidoformate

Chemical Property:

• Refractive Index: 1.6190 (estimate)
• Boiling Point: 261.22°C (rough estimate)
• PSA: 76.05000
• Density: 1.3172 (rough estimate)
• LogP: 1.68456
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 143.069476538
• Heavy Atom Count: 10
• Complexity: 176

Purity/Quality:

99% ^*data from raw suppliers

TERT-BUTYL AZIDOFORMATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N=[N+]=[N-]
• Uses: t-Butyl azidoformate is a convenient reagent for the acylation of amines, hydrazines, and similar compounds.

Technology Process of tert-Butyl azidoformate

There total 7 articles about tert-Butyl 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: 100.0%

t-butoxycarbonylhydrazine (870-46-2) → N-(tert-butyloxycarbonyl) azide (1070-19-5)

Guidance literature:

With acetic acid; sodium nitrite; In water; at 0 - 20 ℃; for 2.08333h;

DOI:10.1002/adsc.201600410

Reference yield: 78.0%

tert-butyl chloroformate (24608-52-4) → N-(tert-butyloxycarbonyl) azide (1070-19-5)

Guidance literature:

With sodium azide; 18-crown-6 ether; In tetrahydrofuran; at 20 ℃; for 96h;

DOI:10.1021/ja029931w

Reference yield: 69.0%

→ N-(tert-butyloxycarbonyl) azide (1070-19-5)

Guidance literature:

upstream raw materials:

t-butoxycarbonylhydrazine

phosgene

tert-butyl alcohol

tert-butyl chloroformate

Downstream raw materials:

N^α-(benzyloxycarbonyl)-N^ε-(tert-butoxycarbonyl)-L-lysine methyl ester

N-(tert-butoxycarbonyl)sarcosine

N_α-(1,1-dimethylethoxycarbonyl)-N_δ-(phenylmethoxycarbonyl)-L-ornithine 1,1-dimethylethyl ester

N-[(1,1-dimethylethoxy)carbonyl]-L-alanine 1,1-dimethylethyl ester

Refernces

• 1、 Holzinger, Michael,Abraham, Juergen,Whelan, Paul,Graupner, Ralf,Ley, Lothar,Hennrich, Frank,Kappes, Manfred,Hirsch, Andreas. "Functionalization of single-walled carbon nanotubes with (R-)oxycarbonyl nitrenes". . p. 8566 - 8580. Retrieved 2003.
• 2、 Pozsgay, Vince,Jennings, Harold J.. "AZIDE SYNTHESIS WITH STABLE NITROSYL SALTS". . p. 5091 - 5092. Retrieved 1987.
• 3、 Wippich, Julian,Truchan, Nadina,Bach, Thorsten. "Rhodium-Catalyzed N-tert-Butoxycarbonyl (Boc) Amination by Directed C H Bond Activation". supporting information. p. 2083 - 2087. Retrieved 2016/07/16.
• 4、 -. "Method for producing hematopoietic stem cells using pyrazole compounds". Page/Page column 169. . Retrieved 2016/01/10.