Tetrabutylammonium tribromide explained
Tetrabutylammonium tribromide, abbreviated to TBATB, is a pale orange solid with the formula [N(C<sub>4</sub>H<sub>9</sub>)<sub>4</sub>]Br3. It is a salt of the lipophilic tetrabutylammonium cation and the linear tribromide anion.[1] [2] The salt is sometimes used as a reagent used in organic synthesis as a conveniently weighable, solid source of bromine.
Preparation
The compound is prepared by treatment of solid tetra-n-butylammonium bromide with bromine vapor:[3]
[N(C<sub>4</sub>H<sub>9</sub>)<sub>4</sub>]Br + Br2 → [N(C<sub>4</sub>H<sub>9</sub>)<sub>4</sub>]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.[4]
See also
Notes and References
- Polybromide salts of tetraalkyl and N-heterocyclic cations: New entries into the structural library . Igor D. Gorokh . Sergey A. Adonin . Maxim N. Sokolov . Pavel A. Abramov . Ilya V. Korolkov . Evgeniy Yu. Semitut . Vladimir P. Fedin . . 2018 . 469 . 583–587 . 10.1016/j.ica.2017.10.008 .
- JEPGUG01: tetra-n-butylammonium tribromide . . Cambridge Structural Database
Access Structures
. 2017 . . 10.5517/ccdc.csd.cc1ntw2f .
- Book: Alexander I. . Popov . Robert E. . Buckles . Walter C. . Schumb . John W. . George . Typical Polyhalogen Complex Salts . Inorganic Syntheses. 1957 . 5 . 176–178 . 10.1002/9780470132364.ch47. 978-0-470-13236-4 .
- Book: Michel J. L.. Fournier. Fernando A.. Fernandez. David E.. Nichols. Leo A.. Paquette. Tetrabutylammonium Tribromide. Encyclopedia of Reagents for Organic Synthesis. 2010. 10.1002/047084289X.rt020.pub2. 978-0-471-93623-7.
