26501-54-2

Basic information

• Product Name: TETRABUTYLAMMONIUM NITRITE
• Synonyms: TETRABUTYLAMMONIUM NITRITE;Tetrabutylaminium·nitrous acid anion;Tetrabutylammonium nitrite purum, >=97.0% (NT);TetrabutylaMMoniuM nitrite >=97.0% (NT);tetrabutylazanium:nitrite
• CAS NO: 26501-54-2
• Molecular Formula: C16H36N2O2
• Molecular Weight: 288.47
• EINECS: 247-749-1
• Product Categories: Ammonium Salts;AmmoniumGreener Alternatives: Catalysis;Chemical Synthesis;Ionic Liquids;Phase Transfer Catalysts;Ammonium;Ammonium Salts;Chemical Synthesis;Ionic Liquids;Phase Transfer Catalysts;Specialty Synthesis;Synthetic Reagents
• Mol File: 26501-54-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 99-103 °C
• Appearance: /
• BRN: 6285720
• CAS DataBase Reference: TETRABUTYLAMMONIUM NITRITE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRABUTYLAMMONIUM NITRITE(26501-54-2)
• EPA Substance Registry System: TETRABUTYLAMMONIUM NITRITE(26501-54-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 26501-54-2(Hazardous Substances Data)

Usage

General Description

Tetrabutylammonium nitrite is a chemical compound consisting of tetrabutylammonium cations and nitrite anions. It is commonly used as a reagent in organic synthesis and research laboratories, and is also utilized as a catalyst in various reactions. Tetrabutylammonium nitrite is a strong oxidizing agent and can react explosively with certain organic compounds, making it a potentially hazardous substance to handle. It is important to use proper safety measures when working with tetrabutylammonium nitrite, including wearing appropriate protective equipment and working in a well-ventilated area.

InChI:InChI=1/C16H36N.HNO2/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;2-1-3/h5-16H2,1-4H3;(H,2,3)/q+1;/p-1

Upstream product

• 1643-19-2 tetrabutylammomium bromide 
• 429-41-4 tetrabutyl ammonium fluoride 

Downstream Products

• 1941-27-1 tetrabutylammonium nitrate 
• 3007-95-2 naphthalene-1-carboxylic acid butyl ester 
• 10102-43-9 nitrogen(II) oxide 

Relevant articles and documents

Straightforward synthesis of 1,2-dicyanoalkanes from nitroalkenes and silyl cyanide mediated by tetrabutylammonium fluoride

A straightforward synthesis of 1,2-dicyanoalkanes by reacting nitroalkenes with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride is described. The reaction proceeds through a tandem double Michael addition under mild conditions. Employing the hypervalent silicate generated from trimethylsilyl cyanide and tetrabutylammonium fluoride is essential for achieving this transformation. Mechanistic studies suggest that a small amount of water included in the reaction media plays a key role. This protocol is applicable to various types of substrates including electron-rich and electron-deficient aromatic nitroalkenes, and aliphatic nitroalkenes. Moreover, vinyl sulfones were found to be good alternatives, particularly for electron-deficient nitroalkenes. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 1,2-dicyanoalkanes.