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
• Article Data: 19

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

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/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

• 62995-09-9 N-tert-butyloxycarbonyl dimethyl sulfoximine 
• 42116-56-3 (2-hydrazinocarbonyl-ethyl)-carbamic acid tert-butyl ester 
• 30992-29-1 Boc-Aib-OH 
• 60295-10-5 N'-[1-(4-Methoxy-phenyl)-prop-(E)-ylidene]-hydrazinecarboxylic acid tert-butyl ester 
• 111080-65-0 (pyridin-4-ylmethyl)carbamic acid tert-butyl ester 
• 51857-17-1 tert-butyl N-(6-aminohexyl)carbamate 
• 16644-54-5 N,N'-bis(tert-butoxycarbonyl)-1,6-hexanediamine 
• 90600-20-7 (2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid 
• 60280-45-7 N-Boc-L-methionine sulfone 
• 82409-00-5 N,N'-bis(t-butoxycarbonyl)-1,8-octanediamine 
• 88829-82-7 tert-butyl N-(8-aminooctyl)carbamate 
• 147751-16-4 tert-butyl (methylsulfonyl)carbamate 
• 84758-55-4 N-(tert-butoxycarbonyl)-α-methylalanine methyl ester 
• 53267-93-9 O-methyl-N-tert-butoxycarbonyl-L-tyrosine 

Relevant articles and documents

-

-

Solid-phase synthesis of muramyl dipeptide (MDP) derivatives using a multipin method

Solid-phase synthetic method of muramyl dipeptide derivatives is reported. A diverse library of muramyl dipeptides could be potentially synthesized by acylation, reductive alkylation, sulfonamide formation, urea formation, N-alkylation, amine addition, or component Ugi reactions based on this method for drug screening. (C) 2000 Elsevier Science Ltd. All rights reserved.

The enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to isatin-derived ketimines

An asymmetric organocatalytic addition of fluorinated phenylsulfonylnitromethane to isatin-derived ketimines was developed. The reaction was efficiently catalyzed by a chiral tertiary amine, cinchonine. This methodology provides a new type of optically active compound with two adjacent quaternary carbon stereocenters in good yield (up to 96%), with moderate diastereoselectivity (up to 5.7:1 dr) and excellent enantioselectivity (up to 98/96% ee).

Rhodium-Catalyzed N-tert-Butoxycarbonyl (Boc) Amination by Directed C H Bond Activation

N-tert-Butoxycarbonyl azide (BocN3) was shown to be an efficient and economic source for the directed introduction of N-Boc protected amino groups into the thiophene and benzene nucleus. Yields for the amination of 2-pyridin-2-ylthiophenes (10 examples) were 52–88%. For the amination of the respective benzenes (10 examples) yields between 54% and 99% were recorded with an improved reactivity observed for substrates that bear an electron-withdrawing group. The reaction was applied to short total syntheses of the indoloquinoline alkaloids quindoline and cryptolepine. The facile removal of the Boc protecting group was the key to the success of the syntheses. The scope of the reaction was extended to a C(sp3) H bond amination and to the amination of 2-phenyloxazoline. For the amination of 2-pyridin-2-ylbenzene a kinetic deuterium isotope effect of 2.0 was determined. (Figure presented.) .

PYRAZOLE COMPOUNDS HAVING THERAPEUTIC EFFECT ON MULTIPLE MYELOMA

Novel therapeutic agents for myeloma are provided. A therapeutic agent for multiple myeloma containing a pyrazole compound represented by the formula (1): wherein R1 is C1-C6 alkyl, C1-C6 alkyl substituted with R17, C1-C6 haloalkyl, phenyl, phenyl substituted with a R11's or the like, R2 is a hydrogen atom, C1-C6 alkyl, phenyl or phenyl optionally substituted with e R21's or the like, R3 is a hydrogen atom or the like, X is a single bond or —(CR6, R7)n—, each of R4 and R5 is independently C1-C6 alkyl or the like, R6 and R7 are hydrogen atoms or C1-C6 alkyl, R8 is phenyl, phenyl optionally substituted with k R81's or the like, a tautomer of the compound or a pharmaceutically acceptable salt or solvate thereof, as an active ingredient.