| Identification | Back Directory | [Name]
tert-butyl azidoformate | [CAS]
1070-19-5 | [Synonyms]
t-Butyl Azidoformate
tert-butyl azidoformate
Azacitidine Impurity 52
ert-butylN-diazocarbamate
Azido tert-butoxymethanone
(tert-Butoxycarbonyl) azide
tert-butyl N-diazocarbamate
N-(tert-butyloxycarbonyl) azide
Azidoformic acid tert-butyl ester
Azidocarbonic acid tert-butyl ester | [EINECS(EC#)]
213-972-8 | [Molecular Formula]
C5H9N3O2 | [MDL Number]
MFCD01742129 | [MOL File]
1070-19-5.mol | [Molecular Weight]
143.144 |
| Safety Data | Back Directory | [TSCA ]
TSCA listed | [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. |
| Hazard Information | Back Directory | [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 |
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