10442-39-4

Basic information

• Product Name: TETRABUTYLAMMONIUM CYANIDE
• Synonyms: n,n,n-tributyl-1-butanaminiucyanide;TETRABUTYLAMMONIUM CYANIDE;1-Butanaminium, N,N,N-tributyl-, cyanide;Tetrabutylaminium·cyanide;Tetrabutylammonium cyanide technical, >=80%;TetrabutylaMMoniuM cyanide 95%;N,N,N-Tributyl-1-butanaminium cyanide (1:1);tetrabutylazanium:cyanide
• CAS NO: 10442-39-4
• Molecular Formula: CN*C₁₆H₃₆N
• Molecular Weight: 268.48
• EINECS: 233-926-0
• Product Categories: Ammonium Salts;Greener Alternatives: Catalysis;Phase Transfer Catalysts
• Mol File: 10442-39-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 89-92 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• BRN: 3598808
• CAS DataBase Reference: TETRABUTYLAMMONIUM CYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRABUTYLAMMONIUM CYANIDE(10442-39-4)
• EPA Substance Registry System: TETRABUTYLAMMONIUM CYANIDE(10442-39-4)

Safety Data

• Hazard Codes: T+,N
• Statements: 26/27/28-32-50/53
• Safety Statements: 7-28-29-45-60-61
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• F: 3-10
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 10442-39-4(Hazardous Substances Data)

Usage

Description

Tetrabutylammonium cyanide (TBACN) is an organometallic compound with the chemical formula (C4H9)4N?CN. It is a colorless to pale yellow liquid that is soluble in organic solvents and is widely utilized in various chemical reactions and processes due to its unique properties.

Uses

Used in Organic Synthesis:
Tetrabutylammonium cyanide is used as a catalyst for the synthesis of organic compounds, particularly multisubstituted dihydrofurans and pyrrolo[2,1-a]isoquinolines. It facilitates the formation of these complex structures by promoting specific reaction pathways and enhancing the overall yield of the desired products.
Used in Colorimetric Studies:
TBACN can be used as a source of cyanide ion for colorimetric studies, which are essential for the qualitative and quantitative analysis of various compounds. The cyanide ion from TBACN can react with specific reagents to produce a color change, allowing for the detection and measurement of certain substances.
Used in the Preparation of Tetrabutylammonium Fluoride (TBAF):
Tetrabutylammonium cyanide is used as a reactant in the preparation of tetrabutylammonium fluoride (TBAF), a versatile reagent in organic chemistry. TBAF is particularly useful for the removal of silyl ether protecting groups, which are commonly used in the synthesis of complex organic molecules.
Used in the Synthesis of Rhenium-based Single-chain Magnets:
TBACN is employed in the synthesis of rhenium-based single-chain magnets, such as (DMF)4MReCl4(CN)2 (M = Mn, Fe, Co, Ni). These materials exhibit unique magnetic properties and have potential applications in the development of advanced magnetic materials and devices.
Used in the Preparation of Phosphorescent Blue Light-emitting Iridium Complexes:
Tetrabutylammonium cyanide is used in the preparation of phosphorescent blue light-emitting anionic iridium complexes. These complexes are of significant interest due to their potential applications in organic light-emitting diodes (OLEDs) and other optoelectronic devices, where they can provide efficient and long-lasting light emission.

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

Upstream product

• 1923-70-2 tetrabutylammonium perchlorate 
• 151-50-8 potassium cyanide 
• 143-33-9 sodium cyanide 
• 32503-27-8 tetra(n-butyl)ammonium hydrogensulfate 
• 7677-24-9 trimethylsilyl cyanide 
• 429-41-4 tetrabutyl ammonium fluoride 
• 1242065-13-9 CN^(1-)*C₁₆H₃₆N⁽¹⁺⁾*C₃₀H₃₃N₃O₁₂ 
• 773837-37-9 sodium cyanide 

Downstream Products

• 135086-42-9 1-Benzyloxy-2,3-dimethyl-cyclopropanecarbonitrile 
• 5633-57-8 1-methoxy-4-(phenylsulfanyl)benzene 
• 874-90-8 4-methoxybenzonitrile 
• 37984-02-4 3-nitrophenyl phenyl sulfide 
• 98-95-3 nitrobenzene 
• 619-24-9 3-nitrobenzonitrile 
• 4171-83-9 2-nitrophenyl phenyl sulfide 
• 612-24-8 o-nitrobenzonitrile 
• 623-26-7 terephthalonitrile 
• 3459-94-7 1,4-bis(phenylthio)benzene 
• 65662-88-6 phenyl(4-bromophenyl)sulfide 
• 51238-46-1 4-(phenylthio)benzonitrile 
• 108697-88-7 3-cyanophenyl phenyl sulfide 
• 1684-14-6 2,3-diphenylquinoxaline 

Related news

TETRABUTYLAMMONIUM CYANIDE (cas 10442-39-4) catalyzed diasteroselective cyanosilylation of chiral α-hydroxyketones08/01/2019

Tetrabutylammonium cyanide has been used as non-metallic catalyst for the diastereoselective cyanosilylation of α-hydroxyketones derived from the chiral pool. This affords α-substituted-α,β-dihydroxynitriles with high levels of asymmetric induction.detailed

Relevant articles and documents

Stereoselective addition of cyanide reagents to nitrones

An exploration of the diastereoselective addition of cyanide reagents to the nitrone 1 derived from D-glyceraldehyde acetonide to afford mixtures of syn-2 and anti-2 is presented. Trimethylsilyl cyanide was found to add to the nitrone 1 with essentially complete syn-stereoselectivity in excellent yields.

Syntheses and anion binding capabilities of bis(diarylboryl) ferrocenes and related systems

Isomeric diborylated ferrocenes featuring 1,1′-, 1,2-, and 1,3-substitution patterns have been targeted via a combination of electrophilic aromatic substitution and directed ortho-lithiation protocols. While none of these systems are competent for the Lewis acid chelation of fluoride, related systems featuring a mixed B/Si acceptor set capture 1 equiv of fluoride via a Si-F-B bridging motif.

Synthesis of a C3-symmetric furyl-cyclopeptide platform with anion recognition properties

A new furyl amino acid derivative was trimerized to give a linear peptide and finally was cyclized. The newly generated cyclopeptide was subjected to a conformational study in order to be considered as a C3-symmetric platform for the ratio nal design of complex receptors. Moreover, the recognition properties towards cyanide, acetate and chloride anions were studied.