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]

Tetra-n-butylammonium bromide

Names
IUPAC name Tetrabutylammonium bromide
Other names Tetra-n-butylammonium bromide TBAB
Identifiers
CAS Number	1643-19-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:51993
ChEMBL	ChEMBL60696
ChemSpider	66843
ECHA InfoCard	100.015.182
EC Number	216-699-2
PubChem CID	74236
UNII	VJZ168I98R
CompTox Dashboard (EPA)	DTXSID4044400
InChI InChI=1S/C16H36N.BrH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1 Key: JRMUNVKIHCOMHV-UHFFFAOYSA-M InChI=1/C16H36N.BrH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1 Key: JRMUNVKIHCOMHV-REWHXWOFAC
SMILES [Br-].CCCC[N+](CCCC)(CCCC)CCCC
Properties
Chemical formula	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
GHS hazard statements	H302, H315, H319, H335, H411, H412
GHS precautionary statements	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).
verify (what is  ?)
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

• Tetrabutylammonium tribromide, with an additional Br₂ unit
• Tetrabutylammonium fluoride
• Tetrabutylammonium hydroxide

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.