tert-butyl azidoformate
- CAS No.
- 1070-19-5
- Chemical Name:
- tert-butyl azidoformate
- Synonyms
- t-Butyl Azidoformate;Azacitidine Impurity 52;tert-butyl azidoformate;ert-butylN-diazocarbamate;Azido tert-butoxymethanone;tert-butyl N-diazocarbamate;(tert-Butoxycarbonyl) azide;N-(tert-butyloxycarbonyl) azide;Azidoformic acid tert-butyl ester;Azidocarbonic acid tert-butyl ester
- CBNumber:
- CB5892220
- Molecular Formula:
- C5H9N3O2
- Molecular Weight:
- 143.14386
- MOL File:
- 1070-19-5.mol
- MSDS File:
- SDS
- Modify Date:
- 2022/8/1 22:48:44
| Boiling point | 261.22°C (rough estimate) |
|---|---|
| Density | 1.3172 (rough estimate) |
| refractive index | 1.6190 (estimate) |
| EPA Substance Registry System | Carbonazidic acid, 1,1-dimethylethyl ester (1070-19-5) |
tert-butyl azidoformate Chemical Properties,Uses,Production
Uses
t-Butyl azidoformate is a convenient reagent for the acylation of amines, hydrazines, and similar 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/ja01513a049
Tetrahedron 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.
tert-butyl azidoformate Preparation Products And Raw materials
Raw materials
Preparation Products
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