1070-19-5 Usage
Description
Tert-butyl azidoformate is an organic compound that serves as a versatile reagent in various chemical reactions, particularly in the acylation of amines, hydrazines, and similar compounds. It is known for its ability to facilitate the formation of acyl azide intermediates, which can be further transformed into other functional groups, making it a valuable tool in synthetic chemistry.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 1070-19-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,7 and 0 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1070-19:
(6*1)+(5*0)+(4*7)+(3*0)+(2*1)+(1*9)=45
45 % 10 = 5
So 1070-19-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H10N3O2/c1-5(2,3)10-4(9)7-8-6/h6H,1-3H3/q+1
1070-19-5Relevant articles and documents
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Laszlo, Pierre,Polla, Eugenio
, p. 3701 - 3704 (1984)
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Solid-phase synthesis of muramyl dipeptide (MDP) derivatives using a multipin method
Liu, Gang,Zhang, Shuo-De,Xia, Shu-Quan,Ding, Zhen-Kai
, p. 1361 - 1363 (2000)
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
Urban,Franc,Hofmanová,Císa?ová,Vesely
supporting information, p. 9071 - 9076 (2017/11/14)
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
Wippich, Julian,Truchan, Nadina,Bach, Thorsten
supporting information, p. 2083 - 2087 (2016/07/16)
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
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Paragraph 0196; 0197, (2013/10/07)
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.
