Tetrabutylammonium tribromide
Tetrabutylammonium tribromide, abbreviated to TBATB, is a pale orange solid with the formula [N(C4H9)4]Br3. It is a salt of the lipophilic tetrabutylammonium cation and the linear tribromide anion. The salt is sometimes used as a reagent used in organic synthesis as a conveniently weighable, solid source of bromine.
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| Names | |
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| IUPAC name
N,N,N-Tributyl-1-butanaminium tribromide | |
| Other names
TBATB | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.132.625 |
PubChem CID |
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| Properties | |
| C16H36Br3N | |
| Molar mass | 482.183 g·mol−1 |
| Appearance | pale orange solid, red when recrystallized from DMF[1] |
| Melting point | 71 to 76 °C (160 to 169 °F; 344 to 349 K) [2] |
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
The compound is prepared by treatment of solid tetra-n-butylammonium bromide with bromine vapor:[3]
- [N(C4H9)4]Br + Br2 → [N(C4H9)4]Br3
Instead of bromine, tetra-n-butylammonium bromide can also be reacted with vanadium pentoxide and aqueous hydrogen peroxide, or alternatively with ceric ammonium nitrate.[1]
References
- Fournier, Michel J. L.; Fernandez, Fernando A.; Nichols, David E. (2010). "Tetrabutylammonium Tribromide". In Paquette, Leo A. (ed.). Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt020.pub2.
- Tetrabutylammonium tribromide at Sigma-Aldrich
- Popov, Alexander I.; Buckles, Robert E.; Schumb, Walter C.; George, John W. (1957). "Typical Polyhalogen Complex Salts". Inorganic Syntheses. 5: 176–178. doi:10.1002/9780470132364.ch47.
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