Tetrabutylammonium tribromide

Tetrabutylammonium tribromide
Names
	IUPAC name N,N,N-Tributyl-1-butanaminium tribromide
	Other names TBATB
Identifiers
CAS Number	38932-80-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	2005880 ;
ECHA InfoCard	100.132.625
PubChem CID	2723680;
CompTox Dashboard (EPA)	DTXSID801028457 ;
	InChI 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 ; 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;
	SMILES Br[Br-]Br.CCCC[N+](CCCC)(CCCC)CCCC;
Properties
Chemical formula	C16H36Br3N
Molar mass	482.183 g·mol−1
Appearance	pale orange solid, red when recrystallized from DMF
Melting point	71 to 76 °C (160 to 169 °F; 344 to 349 K)
	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

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.

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]

References

^ ^a ^b 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.
^ Tetrabutylammonium tribromide at Sigma-Aldrich
^ 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.
^ "JEPGUG01: tetra-n-butylammonium tribromide". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. 2017. doi:10.5517/ccdc.csd.cc1ntw2f.
^ 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.

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[e-EROS-1] 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.

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Preparation

See also

References