Tetrabutylammonium bromide

"TBAB" redirects here. For t-butylamine borane, see borane tert-butylamine complex.

Tetra-n-butylammonium bromide

Names
Preferred IUPAC name N,N,N-Tributylbutan-1-aminium bromide
Other names Tetra-n-butylammonium bromide TBAB
Identifiers
CAS Number	1643-19-2  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:51993  Y
ChEMBL	ChEMBL60696  Y
ChemSpider	66843  Y
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 Y Key: JRMUNVKIHCOMHV-UHFFFAOYSA-M Y 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
Density	1.18 g/cm3 [1]
Melting point	125 °C (257 °F; 398 K) [2] Decomposes at 133°C [3]
Solubility in water	600 g/L (20 °C)
Solubility	Soluble in dichloromethane and ethanol, slightly soluble in toluene [4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Harmful
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335, H411, H412
Precautionary statements	P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
Related compounds
Other anions	Tetrabutylammonium tribromide, Tetra-n-butylammonium fluoride, Tetrabutylammonium 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). Y  verify  (what is  YN ?) Infobox references

Tetrabutylammonium bromide (TBAB) is a quaternary ammonium salt with a bromide commonly used as a phase transfer catalyst. ^[5] It is used to prepare many other tetrabutylammonium salts by salt metathesis reactions. The anhydrous form is a white solid. ^[4]

In addition to being cheap, tetrabutylammonium bromide is also environmentally friendly, has a greater degree of selectivity, is operationally simple, non-corrosive, and can be recycled easily as well. ^[6]

Preparation and reactions

Tetrabutylammonium bromide can be prepared by the alkylation of tributylamine with 1-bromobutane. ^[4]

Tetrabutylammonium bromide is used to prepare other salts of the tetrabutylammonium cation by salt metathesis reactions. ^[7]

It serves as a source of bromide ions for substitution reactions. It is a commonly used phase transfer catalyst. As its melting point is just over 100 °C and decreases in the presence of other reagents, it can be considered an ionic liquid. ^[4]

Role in semi-clathrate formation

TBAB is being extensively studied as a thermodynamic promoter in the formation of semi-clathrate hydrates which greatly brings down the pressure - temperature requirement for forming gas hydrates. ^[8]

See also

• Tetrabutylammonium tribromide, with an additional Br₂ unit
• Tetrabutylammonium fluoride
• Tetrabutylammonium chloride
• Tetrabutylammonium iodide

References

1. Mark R. J. Elsegood (2011). "Tetra-n-butylammonium bromide: a redetermination at 150 K addressing the merohedral twinning". Acta Crystallographica Section E. 67 (10): 2599. Bibcode:2011AcCrE..67o2599E. doi:10.1107/S1600536811032612. PMC   3201250 . PMID   22058750.
2. Reichenbach, Judith; Ruddell, Stuart A.; González-Jiménez, Mario; Lemes, Julio; Turton, David A.; France, David J.; Wynne, Klaas (31 May 2017). "Phonon-like Hydrogen-Bond Modes in Protic Ionic Liquids". Journal of the American Chemical Society. 139 (21). See bottom of Supporting Information: 7160–7163. doi: 10.1021/jacs.7b03036 .
3. Applied Catalysis A: General 241 (2003) 227–233
4. Charette, André B.; Chinchilla, Rafael; Nájera, Carmen (2007). "Tetrabutylammonium Bromide". In Paquette, Leo A. (ed.). Encyclopedia of Reagents for Organic Synthesis . doi:10.1002/047084289X.rt011.pub2. ISBN   978-0471936237.
5. Henry J. Ledon (1988). "Diazo transfer by means of phase-transfer catalysis: di-tert-butyl diazomalonate". Organic Syntheses ; Collected Volumes, vol. 6, p. 414.
6. Chary, M.V.; Keerthysri, N.C.; Vupallapati, S.V.N.; Lingaiah, N.; Kantevari, S. (2008). "Tetrabutylammonium bromide (TBAB) in isopropanol: An efficient, novel, neutral and recyclable catalytic system for the synthesis of 2,4,5-trisubstituted imidazoles". Catal. Commun. 9 (10): 2013–2017. doi:10.1016/j.catcom.2008.03.037.
7. Klemperer, W. G. (1990). "Tetrabutylammonium Isopolyoxometalates". Inorganic Syntheses. Vol. 27. pp. 74–85. doi:10.1002/9780470132586.ch15. ISBN   9780470132586., Bojes, J.; Chivers, T.; Drummond, I. (1978). "Heptathiazocine(Heptasulfurimide) and Tetrabutylammonium Tetrathionitrate". Inorganic Syntheses. Vol. 18. pp. 203–206. doi:10.1002/9780470132494.ch36. ISBN   9780470132494., Ceriotti, A.; Longoni, G.; Marchionna, M. (1989). "Bis(Tetrabutylammonium) Hexa-μ-Carbonyl-Hexacarbonylhexaplatinate(2 -), [N(C ₄ H ₉ ) ₄]₂[Pt ₆ (Co) ₆ (μ-Co) ₆]". Inorganic Syntheses. Vol. 26. pp. 316–319. doi:10.1002/9780470132579.ch57. ISBN   978-0-471-50485-6.;Christou, George; Garner, C. David; Balasubramaniam, A.; Ridge, Brian; Rydon, H. N. (1982). "9. Tetranuclear Iron-Sulfur and Iron-Selenium Clusters". Tetranuclear Iron-Sulfur and Iron-Selenium Clusters. Inorganic Syntheses. Vol. 21. pp. 33–37. doi:10.1002/9780470132524.ch9. ISBN   9780470132524..
8. Meysel, Philipp; Oellrich, Lothar; Raj Bishnoi, P.; Clarke, Matthew A. (October 2011). "Experimental investigation of incipient equilibrium conditions for the formation of semi-clathrate hydrates from quaternary mixtures of (CO2+ N2+ TBAB + H2O)" . The Journal of Chemical Thermodynamics. 43 (10): 1475–1479. doi:10.1016/j.jct.2011.04.021. ISSN   0021-9614.