Tetra-n-butylammonium bromide

Tetra-n-butylammonium bromide (TBAB) is a quaternary ammonium salt with a bromide counterion commonly used as a phase transfer catalyst.[2] It is used to prepare many other tetrabutylammonium salts by salt metathesis reactions. The anhydrous form is a white solid.[3]

"TBAB" redirects here. For t-butylamine borane, see borane tert-butylamine complex.
Tetra-n-butylammonium bromide
Names
IUPAC name
Tetrabutylammonium bromide
Other names
  • Tetra-n-butylammonium bromide
  • TBAB
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.015.182
EC Number
  • 216-699-2
UNII
Properties
C16H36BrN
Molar mass 322.368 g/mol
Appearance White solid
Melting point 103 °C (217 °F; 376 K) Decomposes at 133C[1]
Hazards
Main hazards Harmful
GHS pictograms
GHS Signal word Warning
H302, H315, H319, H335, H411, H412
P261, P264, P270, P271, P273, P280, P301+312, P302+352, P304+340, P305+351+338, P312, P321, P330, P332+313, P337+313, P362, P391, P403+233, P405, P501
Related compounds
Other anions
 Tetrabutylammonium tribromide, Tetra-n-butylammonium fluoride, Tetra-n-butylammonium chloride, Tetra-n-butylammonium iodide, Tetrabutylammonium hydroxide
Other cations
 Tetramethylammonium bromide, Tetraethylammonium bromide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

Tetra-n-butylammonium bromide can be prepared by the nucleophilic substitution reaction of tri-n-butylamine with n-butyl bromide.[3]

Properties and uses

Tetra-n-butylammonium bromide is used to prepare other salts of the tetrabutylammonium cation by salt metathesis reactions, and acts as a source of nucleophilic bromide ions for substitution reactions. It is one of the most commonly-used phase transfer catalysts. As its melting point is just over 100 °C and decreases in the presence of other reagents, it can be considered an ionic liquid. As an ionic liquid, it might be used as a solvent in various reactions, for instance cross-coupling reactions.[3]

See also

References
  1. Applied Catalysis A: General 241 (2003) 227–233
  2. Henry J. Ledon (1988). "Diazo transfer by means of phase-transfer catalysis: di-tert-butyl diazomalonate". Organic Syntheses.; Collective Volume, 6, p. 414
  3. Charette, André B.; Chinchilla, Rafael; Nájera, Carmen. "Tetrabutylammonium Bromide". In Paquette, Leo A. (ed.). Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt011.pub2.
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