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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.

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  • 1070-19-5 Structure
  • Basic information

    1. Product Name: tert-butyl azidoformate
    2. Synonyms: tert-butyl azidoformate;(tert-Butoxycarbonyl) azide;Azido tert-butoxymethanone;Azidocarbonic acid tert-butyl ester;Azidoformic acid tert-butyl ester;t-Butyl Azidoformate
    3. CAS NO:1070-19-5
    4. Molecular Formula: C5H9N3O2
    5. Molecular Weight: 143.14386
    6. EINECS: 213-972-8
    7. Product Categories: N/A
    8. Mol File: 1070-19-5.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 261.22°C (rough estimate)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.3172 (rough estimate)
    6. Refractive Index: 1.6190 (estimate)
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: tert-butyl azidoformate(CAS DataBase Reference)
    10. NIST Chemistry Reference: tert-butyl azidoformate(1070-19-5)
    11. EPA Substance Registry System: tert-butyl azidoformate(1070-19-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1070-19-5(Hazardous Substances Data)

1070-19-5 Usage

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

1070-19-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name tert-butyl N-diazocarbamate

1.2 Other means of identification

Product number -
Other names tert-Butyl azidoformate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1070-19-5 SDS

1070-19-5Relevant articles and documents

Functionalization of single-walled carbon nanotubes with (R-)oxycarbonyl nitrenes

Holzinger, Michael,Abraham, Juergen,Whelan, Paul,Graupner, Ralf,Ley, Lothar,Hennrich, Frank,Kappes, Manfred,Hirsch, Andreas

, p. 8566 - 8580 (2003)

Sidewall functionalization of single-walled carbon nanotubes (SWCNTs) via the addition of (R-)-oxycarbonyl nitrenes allows for the covalent binding of a variety of different groups such as alkyl chains, aromatic groups, dendrimers, crown ethers, and oligoethylene glycol units. Such additions lead to a considerable increase in the solubility in organic solvents such as 1,1,2,2-tetrachloroethane (TCE), dimethyl sulfoxide (DMSO), and 1,2-dichlorobenzene (ODCB). The highest solubilities of 1.2 mg/mL were found for SWCNT adducts with nitrenes containing crown ether of oligoethylene glycol moieties in DMSO and TCE, respectively. The presence of chelating donor groups within the addends allowed for the complexation of Cu2+ and Cd2+. Atomic force microscopy (AFM) and transmission electron microscopy (TEM) revealed that the functionalized tubes form thin bundles with typical diameters of 10 nm. The presence of thin bundles in solution is supported by 1H NMR spectroscopy. The elemental composition of the functionalized SWCNT was determined by X-ray photoelectron spectroscopy (XPS). The use of Raman and electron absorption spectroscopy (UV/Vis-nIR) showed that the electronic properties of the SWCNTs are mostly retained after functionalization, indicating a low degree of addition within this series of SWCNT derivatives.

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.

AZIDE SYNTHESIS WITH STABLE NITROSYL SALTS

Pozsgay, Vince,Jennings, Harold J.

, p. 5091 - 5092 (1987)

Aryl and acyl hydrazines were converted to azides in excellent yields by an equimolar amount of nitrosyl terafluoroborate or nitrosyl sulfate.

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.) .

Cesium Carboxylate-Promoted Iridium Catalyzed C-H Amidation/Cyclization with 2,2,2-Trichloroethoxycarbonyl Azide

Zhang, Tao,Wang, Zhen,Hu, Xuejiao,Yu, Meng,Deng, Tianning,Li, Guigen,Lu, Hongjian

, p. 4898 - 4905 (2016/07/06)

An Ir(III)-catalyzed direct C-H amidation/cyclization of benzamides using 2,2,2-trichloroethoxycarbonyl azide (TrocN3) as the aminocarbonyl source is reported. With the aid of cesium carboxylate, the reactions proceed efficiently and with high regioselectivity, producing various functionalized quinazoline-2,4(1H,3H)-diones, which are important building blocks and key synthetic intermediates for biologically and medicinally important compounds. During the reactions, two new C-N bonds were formed by breaking C-H and N-H bonds sequence.

Method for producing hematopoietic stem cells using pyrazole compounds

-

Page/Page column 169, (2016/01/10)

An expanding agent for hematopoietic stem cells and/or hematopoietic progenitor cells useful as a therapy for various hematopoietic diseases and useful for improvement in the efficiency of gene transfer into hematopoietic stem cells for gene therapy is provided. A method of producing hematopoietic stem cells and/or hematopoietic progenitor cells, which comprises expanding hematopoietic stem cells by culturing hematopoietic stem cells ex vivo in the presence of a compound represented by the formula following (I), a tautomer or pharmaceutically acceptable salt of the compound or a solvate thereof (wherein R1 to R8 are as defined in the description).

PYRAZOLE COMPOUNDS HAVING THERAPEUTIC EFFECT ON MULTIPLE MYELOMA

-

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.

NK1 antagonists

-

, (2008/06/13)

A NK1 antagonist having the formula (I), with the variables defined herein, which is useful for treating a number of disorders, including emesis, depression, anxiety and cough. wherein the variables are as defined in the specification. A representative compound of the invention is:

Synthesis of arylglycines by reaction of diethyl N-Boc-iminomalonate with organomagnesium reagents

Calí,Begtrup

, p. 63 - 66 (2007/10/03)

Diethyl N-Boc-iminomalonate (3), prepared on multigram scale, served as a stable and highly reactive electrophilic glycine equivalent which reacted with organomagnesium compounds affording substituted aryl N-Boc-aminomalonates. Subsequent hydrolysis produced arylglycines.

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