Tetrabutylammonium bromide

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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 125 Â°C (257 Â°F; 398 K)[2] Decomposes at 133°C[3]
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:
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 Â°C [77 Â°F], 100 kPa).
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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 Â°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

References

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