Tetrabutylammonium bromide
Chemical compound From Wikipedia, the free encyclopedia
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.[4] It is used to prepare many other tetrabutylammonium salts by salt metathesis reactions. The anhydrous form is a white solid.[3]
Names | |
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Preferred IUPAC name
N,N,N-Tributylbutan-1-aminium bromide | |
Other names
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Identifiers | |
3D model (JSmol) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.015.182 |
EC Number |
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PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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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[2] |
600 g/L (20 °C) | |
Solubility | Soluble in dichloromethane and ethanol, slightly soluble in toluene[3] |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards |
Harmful |
GHS labelling: | |
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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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]
Tetrabutylammonium bromide can be prepared by the alkylation of tributylamine with 1-bromobutane.[3]
Tetrabutylammonium bromide is used to prepare other salts of the tetrabutylammonium cation by salt metathesis reactions.[6]
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.[3]
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.[7]
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