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

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

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 
• 32503-27-8 tetra(n-butyl)ammonium hydrogensulfate 
• 1242065-13-9 CN^(1-)*C₁₆H₃₆N⁽¹⁺⁾*C₃₀H₃₃N₃O₁₂ 
• 773837-37-9 sodium cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 429-41-4 tetrabutyl ammonium fluoride 
• 143-33-9 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 
• 4171-83-9 2-nitrophenyl phenyl sulfide 
• 98-95-3 nitrobenzene 
• 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 
• 128620-44-0 2-(α-cyanobenzalimino)-N,N-dibenzoylaniline 
• 113664-28-1 4-cyano-4′,4′′-dibromotriphenylamine 

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.

Cyclometalated Arylazo Compounds. Part 4. ortho-Cyano-1-aryazonaphthalenes and 3-Amino-2-arylbenzoindazoles from Cyclopalladated 1-Arylazonaphthalenes

The reaction of a cyclopalladated 1-arylazonaphthalene with tetrabutylammonium cyanide leads to an orto-cyano-1-arylazonaphthalene and a 3-amino-aryl-benzoindazole, depending upon whether triphenylphosphine or 1,2-bis(diphenylphosphino)ethane (DIPHOS) is used to monomerize the binuclear Pd(II)-complex.In a similar insertion reaction with cyclohexyl isocyanide the corresponding 3-(N-cyclohexyl)-aminoindazole is formed.A Pd(II)-isocyano complex is shown to be a possible intermediate in that conversion.

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.

IONIC COMPOUND, PROCESS FOR PRODUCING SAME, AND ION-CONDUCTIVE MATERIAL COMPRISING SAME

The present invention provides a method of producing a tetracyanoborate-containing ionic compound in a milder condition more efficiently and less expensively than conventional methods, and a tetracyanoborate-containing ionic compound having a reduced content of impure components. An ionic compound of the present invention is represented by the following general formula (I), has a content of fluorine atom-containing impurities of 3 mol% or less per 100 mol% of the ionic compound, and a method for producing an ionic compound represented by the general formula (I) of the present invention comprises a step of reacting starting materials containing a cyanide and a boron compound. (In the formula, Ktm+ denotes an organic cation [Kt b]m+ or an inorganic cation [Kta]m+; and m denotes an integer of 1 to 3.)

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.

Applications of Phase-Transfer Catalysis, 31. - Tandem-Nucleophile-Electrophile Additions to Alkenes under Phase-Transfer Catalysis

One-pot Michael additions/alkylations of diethyl benzylidenemalonate and ethyl (1-methylpropylidene)cyanoacetate (3) with alkali metal cyanide/phase-transfer (PT) catalyst and alkyl halides in halohydrocarbon solvents yield compounds 2a-f and 4a-d, respectively.It is noteworthy that no conversions occur in the total absence of traces of water.Cinnamates and methacrylates can be cyclo-dimerized by the action of solid cyanide/PT catalyst to give compounds 6 or 8, respectively.

PHOSPHORORGANISCHE VERBINDUNGEN 90 Methodische Ausgestaltung der P-C und P-S-Cyanolyse am Beispiel einiger Heterophosphoniumsalze

Treatment of allylamido-phosphonium salts with dry tetrabutylammonium cyanide in methylenechloride delivers after removal of the allyl group phosphinous acid amides with retention of configuration (P-C-cyanolysis).Allyl-O-alkylphosphonium salts undergo the Arbosov reaction under the above conditions, while allyl-S-alkyl phosphonium salts undergo fission of the P-S bond (P-S cyanolysis).Equally good results were obtained using KCN in methylene chloride accompained by catalytic amounts of 18-crown-6 ether; thus optically active benzyl-methyl-phenyl-phosphine-sulfid gave the corresponding phosphine with retention of configuration.Dithiophosphinic acid esters and thiophosphinic acid amides, after conversion to the corresponding quasiphosphonium salts via S-alkylation and subsequent treatment with tetrabutylammonium cyanide in methylenechloride, also give the corresponding thiophosphinous acid ester and phosphinous acid amide respectively.Thiophosphinic acid O-alkyl esters (R2P(S)OR') give however the thiophosphinic S-alkyl ester (R2P(O)SR') via an Arbusov reaction.The P-C cyanolysis of allyl-triphenylphosphoniumbromide using KCN/18-crown-6 or tetrabutylammonium cyanide in aprotic medium stops at the stage of the intermediary red-coloured ylide; addition of a proton-donor then results in the subsequent rearrangement to the corresponding propenyl-phosphonium salt.