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Tetrabutylammonium bromide information


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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:51993 checkY
ChEMBL
  • ChEMBL60696 checkY
ChemSpider
  • 66843 checkY
ECHA InfoCard 100.015.182 Edit this at Wikidata
EC Number
  • 216-699-2
PubChem CID
  • 74236
UNII
  • VJZ168I98R
CompTox Dashboard (EPA)
  • DTXSID4044400 Edit this at Wikidata
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 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
SMILES
  • [Br-].CCCC[N+](CCCC)(CCCC)CCCC
Properties
Chemical formula
C16H36BrN
Molar mass 322.368 g/mol
Appearance White solid
Melting point 103 °C (217 °F; 376 K) Decomposes at 133C[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Harmful
GHS labelling:
Pictograms
GHS07: Exclamation markGHS09: Environmental hazard
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).
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Infobox references

Tetrabutylammonium bromide (TBAB) is a quaternary ammonium salt with a bromide commonly used as a phase transfer catalyst.[2] It is used to prepare many other tetrabutylammonium salts by salt metathesis reactions. The anhydrous form is a white solid.[3]

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.[4]

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

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Tetrabutylammonium bromide

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Tetrabutylammonium bromide (TBAB) is a quaternary ammonium salt with a bromide commonly used as a phase transfer catalyst. It is used to prepare many other...

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Tetrabutylammonium

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desilylation reagent. tetrabutylammonium bromide, a precursor to other tetrabutylammonium salts via salt metathesis reactions. tetrabutylammonium iodide, a low...

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Tetrabutylammonium tribromide

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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...

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Tetrabutylammonium chloride

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a precursor to other tetrabutylammonium salts. Often tetrabutylammonium bromide is preferred as a source of tetrabutylammonium because it is less hygroscopic...

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Williamson ether synthesis

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facile. Finally, phase transfer catalysts are sometimes used (e.g. tetrabutylammonium bromide or 18-crown-6) in order to increase the solubility of the alkoxide...

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Caesium chloride

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}C}}]{ArCH=N-C(C2H4COOCH3)(CH3)-COOC(CH3)3}}}} where TBAB is tetrabutylammonium bromide (interphase catalyst) and CPME is a cyclopentyl methyl ether (solvent)...

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Diallyl disulfide

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synthesized from the same starting materials, but in air and using tetrabutylammonium bromide as a catalyst. The corresponding yield is below 82%. The major...

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Methyl fluoroacetate

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chloride [(CH3(CH2)11)(CH3)3N]+Cl−, tetrabutylammonium chloride [(CH3(CH2)3)4N]+Cl−, tetrabutylammonium bromide [(CH3(CH2)3)4N]+Br−, or tetramethylammonium...

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Quaternary ammonium cation

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of the hydroxide salts such as tetramethylammonium hydroxide and tetrabutylammonium hydroxide even at elevated temperatures. The halflife of Me4NOH in...

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Cyclopropenium ion

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the chloride at the anomeric carbon, the compound is iodinated with tetrabutylammonium iodide. This iodine can thereafter be substituted by any ROH group...

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Octahydrotriborate

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It forms a variety of salts that are colorless and air-stable. The tetrabutylammonium salt is soluble in organic solvents such as acetonitrile and methylene...

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Counterion

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organometallic chemistry. The arsonium salt is also well known. The bromide salt of tetrabutylammonium, one of the most common counter cations. Many analogous "quat...

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Bromobenzenes

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presence of catalytic PdCl 2(NCPh) 2 and triphenylphosphine (PPh 3), tetrabutylammonium iodide (TBAI) as a phase-transfer catalyst, and sodium hydroxide as...

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Tetraethylammonium

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prepare lipophilic salts of inorganic anions. It is used similarly to tetrabutylammonium, the difference being that its salts are less lipophilic, more easily...

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Hunsdiecker reaction

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synthesizes (E)-β-arylvinyl halides. For a green metal-free reaction, tetrabutylammonium trifluoroacetate serves as an alternative catalyst. However, it only...

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Dichlorocarbene

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hydroxide. A phase transfer catalyst, for instance benzyltriethylammonium bromide, facilitates the migration of the hydroxide in the organic phase. HCCl3...

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Ionic liquid

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ammonium cations also form ILs, e.g. tetraethylammonium (TEA) and tetrabutylammonium (TBA). Typical anions in ionic liquids include the following: tetrafluoroborate...

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Rhenium compounds

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perrhenic acid. Addition of tetrabutylammonium chloride to aqueous solutions of sodium perrhenate gives tetrabutylammonium perrhenate, which is soluble...

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Fluoride

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salts of naked fluoride include tetramethylammonium fluoride and tetrabutylammonium fluoride. Cobaltocenium fluoride is another example. However, they...

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Ester

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Synthesis of Esters from Carboxylic Acids and Alkyl Halides Using Tetrabutylammonium Fluoride". Journal of Oleo Science. 63 (5): 539–544. doi:10.5650/jos...

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Trifluoromethylation

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example is the trifluoromethylation of cyclohexanone in THF using tetrabutylammonium fluoride. The substrates can be aryl halides. Potassium...

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Holton Taxol total synthesis

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synthesis include 4-pentenal, m-chloroperoxybenzoic acid, methyl magnesium bromide and phosgene. Two key chemical transformations in this sequence are a Chan...

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Onium ion

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tetraethylammonium, (CH3CH2)4N+ tetrapropylammonium, (CH3(CH2)2)4N+ tetrabutylammonium, (CH3(CH2)3)4N+ or abbreviated Bu4N+ trimethyl ammonium compounds...

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