Tetrabutylammonium tribromide

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Tetrabutylammonium tribromide
Tetrabutylammonium tribromide.svg
Names
IUPAC name
N,N,N-Tributyl-1-butanaminium tribromide
Other names
TBATB
Identifiers
3D model (JSmol)
ChemSpider
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PubChem CID
  • InChI=1S/C16H36N.Br3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-3-2/h5-16H2,1-4H3;/q+1;-1 Yes check.svgY
    Key: XXSLZJZUSYNITM-UHFFFAOYSA-N Yes check.svgY
  • InChI=1S/C16H36N.Br3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-3-2/h5-16H2,1-4H3;/q+1;-1
  • InChI=1S/C16H36N.Br3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-3-2/h5-16H2,1-4H3;/q+1;-1
    Key: XXSLZJZUSYNITM-UHFFFAOYSA-N
  • Br[Br-]Br.CCCC[N+](CCCC)(CCCC)CCCC
Properties
C16H36Br3N
Molar mass 482.183 g·mol−1
Appearancepale 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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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. [3] [4] The salt is sometimes used as a reagent used in organic synthesis as a conveniently weighable, solid source of bromine.

Contents

Preparation

The compound is prepared by treatment of solid tetra-n-butylammonium bromide with bromine vapor: [5]

[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]

See also

References

  1. 1 2 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. ISBN   978-0-471-93623-7.
  2. ↑ Tetrabutylammonium tribromide at Sigma-Aldrich
  3. ↑ Igor D. Gorokh; Sergey A. Adonin; Maxim N. Sokolov; Pavel A. Abramov; Ilya V. Korolkov; Evgeniy Yu. Semitut; Vladimir P. Fedin (2018). "Polybromide salts of tetraalkyl and N-heterocyclic cations: New entries into the structural library". Inorg. Chim. Acta . 469: 583–587. doi:10.1016/j.ica.2017.10.008.
  4. ↑ "JEPGUG01: tetra-n-butylammonium tribromide". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. 2017. doi:10.5517/ccdc.csd.cc1ntw2f.
  5. ↑ Popov, Alexander I.; Buckles, Robert E.; Schumb, Walter C.; George, John W. (1957). "Typical Polyhalogen Complex Salts". Inorganic Syntheses. Inorganic Syntheses. Vol. 5. pp. 176–178. doi:10.1002/9780470132364.ch47. ISBN   978-0-470-13236-4.{{cite book}}: ISBN / Date incompatibility (help)


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