993-22-6

Basic information

• Product Name: Tetrabutylammonium azide
• Synonyms: TETRA-N-BUTYLAMMONIUM AZIDE;TETRABUTYLAMMONIUM AZIDE;n,n,n-tributyl-1-butanaminiuazide;N,N,N-Tributyl-1-butanaminium azide;Tetra-n-butylammonium azide, 90+%;1-Butanaminium, N,N,N-tributyl-, azide;1-Butanaminium, N,N,N-tributyl-, azide (1:1);Tetrabutylammonium a
• CAS NO: 993-22-6
• Molecular Formula: C₁₆H₃₆N*N₃
• Molecular Weight: 284.48
• Product Categories: Ammonium Polyhalides, etc. (Quaternary);Quaternary Ammonium Compounds;Azidation/Diazo TransferChemical Ligation;Azide Sources;Click Chemistry;C-X Bond Formation (Non-Halogen);Synthetic Reagents
• Mol File: 993-22-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 84-88°C
• Appearance: White to Yellow
• Storage Temp.: Refrigerator
• Water Solubility: Soluble in water
• Sensitive: Hygroscopic
• CAS DataBase Reference: Tetrabutylammonium azide(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrabutylammonium azide(993-22-6)
• EPA Substance Registry System: Tetrabutylammonium azide(993-22-6)

Safety Data

• Hazard Codes: T,N
• Statements: 11-50/53-36/37/38-32-25
• Safety Statements: 15-36/37/39-45-61-60-26
• RIDADR: 1325
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 993-22-6(Hazardous Substances Data)

Usage

Description

Tetrabutylammonium azide is a chemical compound with the formula (C4H9)4N4. It is a quaternary ammonium azide that is soluble in organic solvents and has a wide range of applications in various chemical reactions and processes.

Uses

Used in Organic Synthesis:
Tetrabutylammonium azide is used as a reagent for the synthesis of various organic compounds, including heteroarylannulated bicyclic morpholines, cyanimide-based inhibitors of cathepsin C, and trimethylene carbonate. It serves as a source of azide ions, which can be used in various organic reactions, such as the formation of C-N bonds and the conversion of primary azides to nitriles.
Used in Catalysis:
Tetrabutylammonium azide is also used as a catalyst for the formation of cyclic carbonates. It promotes the reaction between epoxides and carbon dioxide, leading to the formation of cyclic carbonates, which are valuable intermediates in the synthesis of various chemicals and pharmaceuticals.
Used in Substitution Reactions:
In the field of organoboron chemistry, tetrabutylammonium azide is used as a reagent for substitution reactions at tetracoordinate boron centers. It can facilitate the exchange of functional groups on boron-containing compounds, enabling the synthesis of new organoboron derivatives with potential applications in materials science and catalysis.
Used in Aerobic Oxidative Transformation:
Tetrabutylammonium azide can be employed in the aerobic oxidative transformation of primary azides to nitriles. This reaction is an efficient method for the synthesis of nitriles, which are important building blocks in organic chemistry and can be used in the preparation of a wide range of compounds, including pharmaceuticals, agrochemicals, and polymers.

Upstream product

• 2472-88-0 tetrabutylammonium sulfate 
• 1112-67-0 tetrabutyl-ammonium chloride 
• 2052-49-5 tetra(n-butyl)ammonium hydroxide 
• 1643-19-2 tetrabutylammomium bromide 
• 32503-27-8 tetra(n-butyl)ammonium hydrogensulfate 

Downstream Products

• 90-96-0 bis(p-methoxyphenyl)methanone 
• 72031-50-6 1,1,3,4,6,6-hexakis(p-methoxyphenyl)-2,5-diaza-1,3,5-hexatriene 
• 123-11-5 4-methoxy-benzaldehyde 
• 171962-22-4 (+)-(4R)-4-Acetamido-1'-[2-(4-cyanophenyl)ethyl]-3,4-dihydro-6-methoxyspiro(2H-1-benzopyran-2,4'-piperidine) hydrochloride 
• 1218795-81-3 N(C₄H₉)4⁽¹⁺⁾*N(U(N(C(CH₃)3)C₆H₃(CH₃)2)3)2^(1-)=N(C₄H₉)4N(U(NC₄H₉C₆H₃(CH₃)2)3)2 
• 1364430-61-4 CH₃SC₁₂H₈B(N₃)C₁₀H₆B(C₆H₂(CH₃)3)2 

Relevant articles and documents

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Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines

Catalytic, intermolecular hydroaminoalkylation (HAA) of styrenes provides a powerful disconnection for pharmacologically relevant γ-arylamines, but current methods cannot utilize unprotected primary alkylamines as feedstocks. Metal-catalyzed HAA protocols are also highly sensitive to α-substitution on the amine partner, and no catalytic solutions exist for α-tertiary γ-arylamine synthesis via this approach. We report a solution to these problems using organophotoredox catalysis, enabling a direct, modular, and sustainable preparation of α-(di)substituted γ-arylamines, including challenging electron-neutral and moderately electron-rich aryl groups. A broad range of functionalities are tolerated, and the reactions can be run on multigram scale in continuous flow. The method is applied to a concise, protecting-group-free synthesis of the blockbuster drug Fingolimod, as well as a phosphonate mimic of itsin vivoactive form (by iterative α-C-H functionalization of ethanolamine). The reaction can also be sequenced with an intramolecularN-arylation to provide a general and modular access to valuable (spirocyclic) 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydronaphthyridines. Mechanistic and kinetic studies support an irreversible hydrogen atom transfer activation of the alkylamine by the azidyl radical and some contribution from a radical chain. The reaction is photon-limited and exhibits a zero-order dependence on amine, azide, and photocatalyst, with a first-order dependence on styrene.

A total synthesis of (+)-negamycin through isoxazolidine allylation

The β-amino acid antibiotic (+)-negamycin has been synthesised in ten steps from epichlorohydrin via Sakurai allylation of an isoxazolidine intermediate. The key allylation reaction proceeded with complete trans-selectivity, which is attributed to electrostatic attraction between the chlorine atom and the iminium ion in the Sakurai intermediate. This journal is the Partner Organisations 2014.