Tetrabutylammonium bromide

Last updated
Tetra-n-butylammonium bromide
Tetrabutylammonium bromide.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 216-699-2
PubChem CID
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 Yes check.svgY
    Key: JRMUNVKIHCOMHV-UHFFFAOYSA-M Yes check.svgY
  • 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
AppearanceWhite 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:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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]

Preparation and reactions

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]

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. [7]

See also

Related Research Articles

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<span class="mw-page-title-main">Tetraethylammonium</span> Polyatomic ion (N(C₂H₅)₄, charge +1)

Tetraethylammonium (TEA) is a quaternary ammonium cation with the chemical formula [Et4N]+, consisting of four ethyl groups attached to a central nitrogen atom. It is a counterion used in the research laboratory to prepare lipophilic salts of inorganic anions. It is used similarly to tetrabutylammonium, the difference being that its salts are less lipophilic, more easily crystallized and more toxic.

<span class="mw-page-title-main">Tetrabutylammonium hydroxide</span> Chemical compound

Tetrabutylammonium hydroxide is the chemical compound with the formula (C4H9)4NOH, abbreviated Bu4NOH with the acronym TBAOH or TBAH. This species is employed as a solution in water or alcohols. It is a common base in organic chemistry. Relative to more conventional inorganic bases, such as KOH and NaOH, Bu4NOH is more soluble in organic solvents.

<span class="mw-page-title-main">Phosphonium</span> Family of polyatomic cations containing phosphorus

In chemistry, the term phosphonium describes polyatomic cations with the chemical formula PR+
4
. These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions.

<span class="mw-page-title-main">Triphenylphosphine</span> Chemical compound

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

<span class="mw-page-title-main">Rhodium(III) chloride</span> Chemical compound

Rhodium(III) chloride refers to inorganic compounds with the formula RhCl3(H2O)n, where n varies from 0 to 3. These are diamagnetic red-brown solids. The soluble trihydrated (n = 3) salt is the usual compound of commerce. It is widely used to prepare compounds used in homogeneous catalysis.

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In chemistry, a phase-transfer catalyst or PTC is a catalyst that facilitates the transition of a reactant from one phase into another phase where reaction occurs. Phase-transfer catalysis is a special form of catalysis and can act through homogeneous catalysis or heterogeneous catalysis methods depending on the catalyst used. Ionic reactants are often soluble in an aqueous phase but insoluble in an organic phase in the absence of the phase-transfer catalyst. The catalyst functions like a detergent for solubilizing the salts into the organic phase. Phase-transfer catalysis refers to the acceleration of the reaction upon the addition of the phase-transfer catalyst.

Tetra-<i>n</i>-butylammonium fluoride Chemical compound

Tetra-n-butylammonium fluoride, commonly abbreviated to TBAF and n-Bu4NF, is a quaternary ammonium salt with the chemical formula (CH3CH2CH2CH2)4N+F. It is commercially available as the white solid trihydrate and as a solution in tetrahydrofuran. TBAF is used as a source of fluoride ion in organic solvents.

<span class="mw-page-title-main">Titanocene dichloride</span> Chemical compound

Titanocene dichloride is the organotitanium compound with the formula (η5-C5H5)2TiCl2, commonly abbreviated as Cp2TiCl2. This metallocene is a common reagent in organometallic and organic synthesis. It exists as a bright red solid that slowly hydrolyzes in air. It shows antitumour activity and was the first non-platinum complex to undergo clinical trials as a chemotherapy drug.

<span class="mw-page-title-main">Tetraphenylphosphonium chloride</span> Chemical compound

Tetraphenylphosphonium chloride is the chemical compound with the formula [(C6H5)4P]Cl, abbreviated Ph4PCl or PPh4Cl or [PPh4]Cl, where Ph stands for phenyl. Tetraphenylphosphonium and especially tetraphenylarsonium salts were formerly of interest in gravimetric analysis of perchlorate and related oxyanions. This colourless salt is used to generate lipophilic salts from inorganic and organometallic anions. Thus, [Ph4P]+ is useful as a phase-transfer catalyst, again because it allows inorganic anions to dissolve in organic solvents.

Martin Arthur Bennett FRS is an Australian inorganic chemist. He gained recognition for studies on the co-ordination chemistry of tertiary phosphines, olefins, and acetylenes, and the relationship of their behaviour to homogeneous catalysis.

<span class="mw-page-title-main">Potassium hexachloroplatinate</span> Chemical compound

Potassium hexachloroplatinate is the inorganic compound with the formula K2PtCl6. It is a yellow solid that is an example of a comparatively insoluble potassium salt. The salt features the hexachloroplatinate(IV) dianion, which has octahedral coordination geometry.

<span class="mw-page-title-main">(Cymene)ruthenium dichloride dimer</span> Chemical compound

(Cymene)ruthenium dichloride dimer is the organometallic compound with the formula [(cymene)RuCl2]2. This red-coloured, diamagnetic solid is a reagent in organometallic chemistry and homogeneous catalysis. The complex is structurally similar to (benzene)ruthenium dichloride dimer.

<span class="mw-page-title-main">Tetrabutylammonium tribromide</span> Chemical compound

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 cation and the linear tribromide anion. The salt is sometimes used as a reagent used in organic synthesis as a conveniently weighable, solid source of bromine.

Organorhenium chemistry describes the compounds with Re−C bonds. Because rhenium is a rare element, relatively few applications exist, but the area has been a rich source of concepts and a few useful catalysts.

<span class="mw-page-title-main">Tetrabutylammonium</span> Polyatomic ion (N(C₄H₉)₄, charge +1)

Tetrabutylammonium is a quaternary ammonium cation with the formula [N(C4H9)4]+, also denoted [NBu4]+. It is used in the research laboratory to prepare lipophilic salts of inorganic anions. Relative to tetraethylammonium derivatives, tetrabutylammonium salts are more lipophilic but crystallize less readily.

<span class="mw-page-title-main">Tetramethylammonium fluoride</span> Chemical compound

Tetramethyl­ammonium fluoride is the quaternary ammonium salt with the formula (CH3)4NF. This hygroscopic white solid is a source of “naked fluoride": fluoride ions not complexed with a metal atom. Most other soluble salts of fluoride are in fact bifluorides, HF2. Historically, there have been two main approaches to prepare tetramethyl­ammonium fluoride: hydrofluoric acid neutralization of tetramethyl­ammonium hydroxide, and salt metathesis between different ammonium salts and inorganic fluoride sources, such as KF or CsF. Because the fluoride anion is extremely basic, the salt slowly reacts with acetonitrile, inducing dimerization to CH3C(NH2)=CHCN, which co-crystallizes.

<span class="mw-page-title-main">Tetrabutylammonium chloride</span> Quaternary ammonium salt of chloride

Tetrabutylammonium chloride is the organic compound with the formula [(CH3CH2CH2CH2)4N]+Cl, often abbreviated as [Bu4N]Cl, where Bu stands for n-butyl. A white water-soluble solid, it is a quaternary ammonium salt of chloride. It is a precursor to other tetrabutylammonium salts. Often tetrabutylammonium bromide is preferred as a source of tetrabutylammonium because it is less hygroscopic than the chloride.

Rhenium compounds are compounds formed by the transition metal rhenium (Re). Rhenium can form in many oxidation states, and compounds are known for every oxidation state from -3 to +7 except -2, although the oxidation states +7, +4, and +3 are the most common. Rhenium is most available commercially as salts of perrhenate, including sodium and ammonium perrhenates. These are white, water-soluble compounds. The tetrathioperrhenate anion [ReS4] is possible.

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. Applied Catalysis A: General 241 (2003) 227–233
  3. 1 2 3 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.
  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.
  6. 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..
  7. 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.