Tetrabutylammonium

Base Information

• Chemical Name: Tetrabutylammonium
• CAS No.: 10549-76-5
• Molecular Formula: C16H36BrN
• Molecular Weight: 242.469
• Hs Code.: 2923900090
• UNII: CBU2X6BBJR
• DSSTox Substance ID: DTXSID3045011
• Nikkaji Number: J91.255G
• Wikipedia: Tetrabutylammonium
• Wikidata: Q25323965
• Metabolomics Workbench ID: 56635
• ChEMBL ID: CHEMBL1236196
• Mol file: 10549-76-5.mol

Synonyms:Bu(4)NBr;tetra-n-butylammonium dodecylsulfate;tetra-n-butylammonium hexafluorophosphate;tetrabutylammonium;tetrabutylammonium azide;tetrabutylammonium bromide;tetrabutylammonium chloride;tetrabutylammonium cyanide;tetrabutylammonium fluoride;tetrabutylammonium hydrogen sulfate;tetrabutylammonium hydroxide;tetrabutylammonium iodide;tetrabutylammonium monophosphate;tetrabutylammonium nitrate;tetrabutylammonium perchlorate;tetrabutylammonium sulfate;tetrabutylammonium sulfate (1:1), sodium salt

Chemical Property of Tetrabutylammonium

Chemical Property:

• Appearance/Colour: powder
• Melting Point: 100-104℃
• PSA: 0.00000
• LogP: 5.00360
• Water Solubility.: 600 g/L (20℃)
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 12
• Exact Mass: 242.284775153
• Heavy Atom Count: 17
• Complexity: 116

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S37/39:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC[N+](CCCC)(CCCC)CCCC
• General Description: TETRABUTYL AMMONIUM BROMIDE (also known as N,N,N-Tributylbutan-1-aminium bromide or 1-Butanaminium, N,N,N-tributyl-, bromide) is a phase-transfer catalyst used in liquid-liquid two-phase reactions, particularly in the deprotonation and alkylation of carbanion precursors such as phenylacetonitriles. It facilitates the transfer of carbanions between organic and aqueous phases, though its effectiveness can be inhibited by iodide anions, which disrupt the interfacial equilibrium and reduce the basicity of NaOH, thereby suppressing carbanion formation and reaction rates.

Technology Process of Tetrabutylammonium

There total 4 articles about Tetrabutylammonium which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

N-(9-((2R,3S,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-((tert-butyldimethylsilyl)oxy)-4-fluorotetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide → teterabutylammonium (10549-76-5) + N-(9-((2R,3S,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;

Reference yield:

chloro-trimethyl-silane (75-77-4) + tetrabutylammonium tetrafluoroborate (429-42-5) → trimethylsilyl fluoride (420-56-4) + teterabutylammonium (10549-76-5)

Guidance literature:

In acetonitrile; at 24 ℃; Inert atmosphere;

Reference yield:

C16H36N(1+)*C9H4O3(1-) → teterabutylammonium (10549-76-5) + Indanetrione anion radical (938-24-9)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide; at 25 ℃; Equilibrium constant;

DOI:10.1021/j100444a018

upstream raw materials:

chloro-trimethyl-silane

tetrabutylammonium tetrafluoroborate

Downstream raw materials:

N(CH₃(CH₂)3)⁽¹⁺⁾ tetrakis[4-[2-(4,6-diamino-1,3,5-triazinyl)]phenyl]borate

Refernces

How iodide anions inhibit the phase-transfer catalyzed reactions of carbanions

10.1016/j.tet.2008.04.042

The research investigates the inhibitory effect of iodide anions on phase-transfer catalyzed reactions of carbanions, which are generated in liquid-liquid two-phase systems using aqueous NaOH. The study suggests that iodide anions preferentially locate in the interfacial region between the organic and aqueous phases, reducing the basic activity of NaOH and disfavoring the deprotonation equilibrium of carbanion precursors. The experiments involved the use of various substituted phenylacetonitriles as carbanion precursors, tetrabutylammonium (TBA) halides as catalysts, and n-propyl halides as alkylating agents. The reactions were carried out in a chlorobenzene/50% aqueous NaOH two-phase system, and the equilibrium contents of carbanions and halides in the organic phase were determined by titration and potentiometric analysis. Gas-liquid chromatography (GLC), nuclear magnetic resonance (NMR), and mass spectrometry (MS) were employed for product analysis and confirmation. The results indicated that the concentration of carbanions in the organic phase and the subsequent reaction rates were influenced by the acidity of the carbanion precursors and the nature of the halide anions, with iodide anions exhibiting the most significant inhibitory effect.