tert-butyl azidoformate

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Products Intro: Product Name:Azido(tert-butoxy)methanone
CAS:1070-19-5
Purity:0.97 Package:mgs,gs,kgs Remarks:A801554
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Products Intro: Product Name:tert-Butyl azidoformate
CAS:1070-19-5
Purity:98% Package:1 kg,5 kg, 10 kg,25kg and 1 MT
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Products Intro: Product Name:tert-butyl N-diazocarbamate
CAS:1070-19-5
Purity:0.98
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Products Intro: Product Name:AZIDO(TERT-BUTOXY)METHANONE
CAS:1070-19-5
Purity:98% HPLC Package:5MG;10MG;50MG;100MG,1G,5G
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Products Intro: Product Name:tert-butyl azidoformate
CAS:1070-19-5
Purity:98% Package:25KG
tert-butyl azidoformate 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;ert-butylN-diazocarbamate;tert-butyl N-diazocarbamate
CAS:1070-19-5
MF:C5H9N3O2
MW:143.14386
EINECS:213-972-8
Product Categories:
Mol File:1070-19-5.mol
tert-butyl azidoformate Structure
tert-butyl azidoformate Chemical Properties
Boiling point 261.22°C (rough estimate)
density 1.3172 (rough estimate)
refractive index 1.6190 (estimate)
EPA Substance Registry SystemCarbonazidic acid, 1,1-dimethylethyl ester (1070-19-5)
Safety Information
MSDS Information
tert-butyl azidoformate Usage And Synthesis
Usest-Butyl azidoformate is a convenient reagent for the acylation of amines, hydrazines, and similar compounds.
Preparationtert-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/ja01513a049
Tetrahedron Letters, 25, p. 3701, 1984 DOI: 10.1016/0040-4039(84)80109-4
Safety ProfileAn 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.
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tert-butyl azidoformate