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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.015.182 Edit this at Wikidata
EC Number
  • 216-699-2
UNII
  • 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 checkY
    Key: JRMUNVKIHCOMHV-UHFFFAOYSA-M checkY
  • 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
  • [Br-].CCCC[N+](CCCC)(CCCC)CCCC
Properties
C16H36BrN
Molar mass 322.368 g/mol
Appearance White solid
Density 1.18 g/cm3[1]
Melting point 103 °C (217 °F; 376 K) Decomposes at 133C[3]
600 g/L (20 °C)
Solubility Soluble in dichloromethane and ethanol, slightly soluble in toluene[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Harmful
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H315, H319, H335, H411, H412
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).
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Tetrabutylammonium bromide (TBAB) is a quaternary ammonium salt with a bromide commonly used as a phase transfer catalyst.[4] It is used to prepare many other tetrabutylammonium salts by salt metathesis reactions. The anhydrous form is a white solid.[2]

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.[5]

  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. ^ a b 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.
  3. ^ Applied Catalysis A: General 241 (2003) 227–233
  4. ^ Henry J. Ledon (1988). "Diazo transfer by means of phase-transfer catalysis: di-tert-butyl diazomalonate". Organic Syntheses; Collected Volumes, vol. 6, p. 414.
  5. ^ 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.