Description

Tetrabutylammonium (TBA⁺) is a quaternary ammonium cation with the molecular formula C₁₆H₃₆N⁺, widely recognized for its role as a phase-transfer catalyst (PTC) in organic synthesis. This highly stable, lipophilic cation facilitates the transfer of anions between aqueous and organic phases, enabling efficient reactions such as nucleophilic substitutions, oxidations, and polymerizations. Its tetrahedral structure, consisting of four butyl groups bonded to a central nitrogen atom, enhances solubility in nonpolar solvents while maintaining reactivity with diverse counterions. Available as salts (e.g., TBA bromide, hydroxide, or tetrafluoroborate), it is a staple in electrochemical applications, including ionic liquids and electrolyte additives for batteries. CAS 10549-76-5.

Key Features:

• High purity (>98%) for reproducible results
• Exceptional phase-transfer efficiency
• Compatible with polar/aprotic solvents (DMF, DMSO, acetonitrile)
• Thermally stable up to 200°C (varies by salt form)
• Widely used in asymmetric synthesis and material science

Properties

• CAS Number: 10549-76-5
• Complexity: 116
• IUPAC Name: tetrabutylammonium
• InChI: InChI=1S/C16H36N/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4/h5-16H2,1-4H3/q+1
• InChI Key: DZLFLBLQUQXARW-UHFFFAOYSA-N
• Exact Mass: 242.284775153
• Molecular Formula: C16H36N+
• Molecular Weight: 242.46
• SMILES: CCCC[N+](CCCC)(CCCC)CCCC
• Monoisotopic Mass: 242.284775153
• Synonyms: Tetrabutylammonium, 10549-76-5, TETRABUTYLAMMONIUM ION, 1-Butanaminium, N,N,N-tributyl-, Ammonium, tetrabutyl-, N,N,N-tributylbutan-1-aminium, tetra-n-butylammonium, CBU2X6BBJR, CHEBI:45825, TETRABUTYLAMMONIUM CATION, DTXSID3045011, Bu(4)NBr, tetra-n-butylammonium dodecylsulfate, TETRABUTYLAMMONIUM(1+), DTXCID1025011, TETRABUTYLAMMONIUM ION(1+), tetrabutylazanium, CHEMBL1236196, tetrabutylamine, UNII-CBU2X6BBJR, tetrabutyammonium, tetra-butylammonium, tetrabutyl ammonium, tetra butyl-ammonium, tetra-butyl ammonium, tetra(n-butyl)ammonium, tetra-n-butyl ammonium, Tetrabutylammonium(+1), TETRABUTHYLAMMONIUM, TAA4, Bu4N+, tetra (n-butyl) ammonium, Tetrabutylammonium ion(+1), SCHEMBL22384, SCHEMBL9080557, SCHEMBL9080560, BDBM50416487, STL194044, AKOS002258926, DB01851, NCGC00334822-01, BP-12611, NS00006689, ST50202982, AB00444480-02, Q27092979, InChI=1/C16H36N/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4/h5-16H2,1-4H3/q+

Tetrabutylammonium salts are indispensable in organic synthesis, enabling reactions like Williamson ether synthesis under mild conditions. In electrochemistry, TBA⁺ serves as a supporting electrolyte for cyclic voltammetry due to its wide potential window. Researchers also employ it to modify electrode surfaces or stabilize reactive intermediates in photoredox catalysis.

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