1070-19-5

Basic information

• Product Name: tert-butyl azidoformate
• Synonyms: tert-butyl azidoformate;(tert-Butoxycarbonyl) azide;Azido tert-butoxymethanone;Azidocarbonic acid tert-butyl ester;Azidoformic acid tert-butyl ester;t-Butyl Azidoformate
• CAS NO: 1070-19-5
• Molecular Formula: C₅H₉N₃O₂
• Molecular Weight: 143.14386
• EINECS: 213-972-8
• Mol File: 1070-19-5.mol

Chemical Properties

• Boiling Point: 261.22°C (rough estimate)
• Appearance: /
• Density: 1.3172 (rough estimate)
• Refractive Index: 1.6190 (estimate)
• CAS DataBase Reference: tert-butyl azidoformate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl azidoformate(1070-19-5)
• EPA Substance Registry System: tert-butyl azidoformate(1070-19-5)

Safety Data

• Hazardous Substances Data: 1070-19-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Tert-butyl azidoformate is used as an acylation reagent for the conversion of amines and hydrazines into their corresponding acylated products. Its application in this field is crucial for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
In the pharmaceutical industry, tert-butyl azidoformate is employed as a key intermediate in the synthesis of bioactive molecules. Its ability to acylate amines and hydrazines allows for the creation of new drug candidates with potential therapeutic applications.
Used in Chemical Research:
Tert-butyl azidoformate is utilized in academic and industrial research settings as a reagent for exploring novel chemical reactions and mechanisms. Its unique reactivity with amines and hydrazines makes it an attractive tool for studying the formation and transformation of acyl azide intermediates.
Used in Agrochemical Development:
In the agrochemical sector, tert-butyl azidoformate is used as a reagent for the synthesis of new pesticides and other crop protection agents. Its role in the acylation process enables the development of innovative compounds with improved efficacy and selectivity.
Overall, tert-butyl azidoformate is a multifaceted reagent with applications spanning across various industries, including organic synthesis, medicinal chemistry, chemical research, and agrochemical development. Its versatility in acylating amines and hydrazines makes it an indispensable tool for the synthesis of a wide range of chemical compounds.

Preparation

tert-Butyl chloroformate was prepared in solution as follows. Dry phosgene was introduced into a solution of 18 g (0.24 mol) of tert-butyl alcohol in 500 ml of anhydrous ether until about 52 g (0.5 mol) had been absorbed and the mixture was cooled in a Dry Ice-acetone bath. Then a solution of 20 g (0.28 mol) of pyridine in 200 ml of anhydrous ether was added dropwise with vigorous stirring. The reaction mixture was stored overnight in a Dry Ice box. The precipitated pyridine hydrochloride was filtered and the volume of the filtrate was reduced to -70 ml at reduced pressure with cooling in an icewater bath.This cold solution of tert-butyl chloroformate was added over 30 min to a vigorously stirred solution of 31.6 g (0.2 mol) of tetramethylguanidinium azide in 200 ml of chloroform; the temperature was kept at 0°C throughout the addition. The bath was removed and the reaction mixture stirred for an additional hour and then poured into 500 nil of ice water containing -2 ml of acetic acid. Extraction with two 60-ml portions of ether followed by careful evaporation of the dried (magnesium sulfate) organic phase gave tert-butyl azidoformate as a pale amber liquid in quantitative yield.The Direct Preparation of tert-Butyl Azidoformate

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 955, 1959 DOI: 10.1021/ja01513a049Tetrahedron Letters, 25, p. 3701, 1984 DOI: 10.1016/0040-4039(84)80109-4

Safety Profile

An unstable shockand heat-sensitive explosive. It may explode above 100°C and iptes at 143°C. When heated to decomposition it emits toxic fumes of NOx. See also AZIDES.

InChI:InChI=1/C5H10N3O2/c1-5(2,3)10-4(9)7-8-6/h6H,1-3H3/q+1

Upstream product

• 870-46-2 t-butoxycarbonylhydrazine 
• 75-44-5 phosgene 
• 75-65-0 tert-butyl alcohol 
• 24608-52-4 tert-butyl chloroformate 
• 75-09-2 dichloromethane 
• 107-11-9 1-amino-2-propene 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 2488-15-5 N-tert-butoxycarbonyl-L-methionine 
• 85006-25-3 N,N-di(tert-butoxycarbonyl)hydroxylamine 
• 16466-61-8 1,2-bis(t-butyloxycarbonyl)hydrazine 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 4248-19-5 tert-butyl carbazate 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 42116-43-8 tert-butyl 2-phenylhydrazine-1-carboxylate 
• 42116-44-9 N-tert-butoxycarbonylbenzylamine 
• 61172-70-1 dimethyl 2-(tert-butoxycarbonylamino)malonate 
• 2389-49-3 N^α-(benzyloxycarbonyl)-N^ε-(tert-butoxycarbonyl)-L-lysine methyl ester 
• 60295-08-1 tert-butyl 2-(diphenylmethylene)hydrazinecarboxylate 
• 60295-13-8 N'-[3,5,5-Trimethyl-cyclohex-2-en-(Z)-ylidene]-hydrazinecarboxylic acid tert-butyl ester 
• 13734-36-6 N-(tert-butoxycarbonyl)sarcosine 

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