Tetrabutylammonium tribromide

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Tetrabutylammonium tribromide
Tetrabutylammonium tribromide.svg
Names
IUPAC name
N,N,N-Tributyl-1-butanaminium tribromide
Other names
TBATB
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.132.625 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • InChI=1S/C16H36N.Br3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-3-2/h5-16H2,1-4H3;/q+1;-1 Yes check.svgY
    Key: XXSLZJZUSYNITM-UHFFFAOYSA-N Yes check.svgY
  • InChI=1S/C16H36N.Br3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-3-2/h5-16H2,1-4H3;/q+1;-1
  • InChI=1S/C16H36N.Br3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-3-2/h5-16H2,1-4H3;/q+1;-1
    Key: XXSLZJZUSYNITM-UHFFFAOYSA-N
  • Br[Br-]Br.CCCC[N+](CCCC)(CCCC)CCCC
Properties
C16H36Br3N
Molar mass 482.183 g·mol−1
Appearancepale orange solid, red when recrystallized from DMF [1]
Melting point 71 to 76 °C (160 to 169 °F; 344 to 349 K) [2]
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 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. [3] [4] The salt is sometimes used as a reagent used in organic synthesis as a conveniently weighable, solid source of bromine.

Contents

Preparation

The compound is prepared by treatment of solid tetra-n-butylammonium bromide with bromine vapor: [5]

[N(C4H9)4]Br + Br2 → [N(C4H9)4]Br3

Instead of bromine, tetra-n-butylammonium bromide can also be reacted with vanadium pentoxide and aqueous hydrogen peroxide, or alternatively with ceric ammonium nitrate. [1]

See also

Related Research Articles

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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">Aluminium bromide</span> Chemical compound

Aluminium bromide is any chemical compound with the empirical formula AlBrx. Aluminium tribromide is the most common form of aluminium bromide. It is a colorless, sublimable hygroscopic solid; hence old samples tend to be hydrated, mostly as aluminium tribromide hexahydrate (AlBr3·6H2O).

A salt metathesis reaction is a chemical process involving the exchange of bonds between two reacting chemical species which results in the creation of products with similar or identical bonding affiliations. This reaction is represented by the general scheme:

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">Vanadium(III) bromide</span> Chemical compound

Vanadium(III) bromide, also known as vanadium tribromide, describes the inorganic compounds with the formula VBr3 and its hydrates. The anhydrous material is a green-black solid. In terms of its structure, the compound is polymeric with octahedral vanadium(III) surrounded by six bromide ligands.

<span class="mw-page-title-main">Tantalum(V) bromide</span> Chemical compound

Tantalum(V) bromide is the inorganic compound with the formula Ta2Br10. Its name comes from the compound's empirical formula, TaBr5. It is a diamagnetic, orange solid that hydrolyses readily. The compound adopts an edge-shared bioctahedral structure, which means that two TaBr5 units are joined by a pair of bromide bridges. There is no bond between the Ta centres. Niobium(V) chloride, niobium(V) bromide, niobium(V) iodide, tantalum(V) chloride, and tantalum(V) iodide all share this structural motif.

Tin(II) bromide is a chemical compound of tin and bromine with a chemical formula of SnBr2. Tin is in the +2 oxidation state. The stability of tin compounds in this oxidation state is attributed to the inert pair effect.

Bromine compounds are compounds containing the element bromine (Br). These compounds usually form the -1, +1, +3 and +5 oxidation states. Bromine is intermediate in reactivity between chlorine and iodine, and is one of the most reactive elements. Bond energies to bromine tend to be lower than those to chlorine but higher than those to iodine, and bromine is a weaker oxidising agent than chlorine but a stronger one than iodine. This can be seen from the standard electrode potentials of the X2/X couples (F, +2.866 V; Cl, +1.395 V; Br, +1.087 V; I, +0.615 V; At, approximately +0.3 V). Bromination often leads to higher oxidation states than iodination but lower or equal oxidation states to chlorination. Bromine tends to react with compounds including M–M, M–H, or M–C bonds to form M–Br bonds.

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

Indium(III) bromide, (indium tribromide), InBr3, is a chemical compound of indium and bromine. It is a Lewis acid and has been used in organic synthesis.

There are three sets of Indium halides, the trihalides, the monohalides, and several intermediate halides. In the monohalides the oxidation state of indium is +1 and their proper names are indium(I) fluoride, indium(I) chloride, indium(I) bromide and indium(I) iodide.

<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.

Tetrabutylammonium bromide Chemical compound

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 tetrabutylammonium salts by salt metathesis reactions. The anhydrous form is a white solid.

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.

Titanium(III) bromide is the inorganic compound with the formula TiBr3. It is a blue black paramagnetic solid with a reddish reflection. It has few applications, although it is a catalyst for the polymerization of alkenes.

<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.

The tetrabromonickelate anion contains a doubly-charged nickel atom (Ni2+) surrounded by four bromide ions in a tetrahedral arrangement. The formula is [NiBr4]2−.

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

Rhodium(III) bromide refers to inorganic compounds of the formula RhBr3(H2O)n where n = 0 or approximately three. Both forms are brown solids. The hydrate is soluble in water and lower alcohols. It is used to prepare rhodium bromide complexes. Rhodium bromides are similar to the chlorides, but have attracted little academic or commercial attention.

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.

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

Tungsten hexabromide, also known as tungsten(VI) bromide, is a chemical compound of tungsten and bromine with the formula WBr6. It is an air-sensitive dark grey powder that decomposes above 200 °C to tungsten(V) bromide and bromine.

References

  1. 1 2 Fournier, Michel J. L.; Fernandez, Fernando A.; Nichols, David E. (2010). "Tetrabutylammonium Tribromide". In Paquette, Leo A. (ed.). Encyclopedia of Reagents for Organic Synthesis . doi:10.1002/047084289X.rt020.pub2. ISBN   978-0-471-93623-7.
  2. Tetrabutylammonium tribromide at Sigma-Aldrich
  3. Igor D. Gorokh; Sergey A. Adonin; Maxim N. Sokolov; Pavel A. Abramov; Ilya V. Korolkov; Evgeniy Yu. Semitut; Vladimir P. Fedin (2018). "Polybromide salts of tetraalkyl and N-heterocyclic cations: New entries into the structural library". Inorg. Chim. Acta . 469: 583–587. doi:10.1016/j.ica.2017.10.008.
  4. "JEPGUG01: tetra-n-butylammonium tribromide". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. 2017. doi:10.5517/ccdc.csd.cc1ntw2f.
  5. Popov, Alexander I.; Buckles, Robert E.; Schumb, Walter C.; George, John W. (1957). "Typical Polyhalogen Complex Salts". Inorganic Syntheses. Inorganic Syntheses. Vol. 5. pp. 176–178. doi:10.1002/9780470132364.ch47. ISBN   978-0-470-13236-4.