Names | |
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IUPAC name N,N,N-Tributyl-1-butanaminium tribromide | |
Other names TBATB | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.132.625 |
PubChem CID | |
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Properties | |
C16H36Br3N | |
Molar mass | 482.183 g·mol−1 |
Appearance | pale 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). |
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.
The compound is prepared by treatment of solid tetra-n-butylammonium bromide with bromine vapor: [5]
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]
Bromine is a chemical element; it has symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig and Antoine Jérôme Balard, its name was derived from the Ancient Greek βρῶμος (bromos) meaning "stench", referring to its sharp and pungent smell.
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.
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).
Tetrapropylammonium perruthenate (TPAP or TPAPR) is the chemical compound described by the formula N(C3H7)4RuO4. Sometimes known as the Ley–Griffith reagent, this ruthenium compound is used as a reagent in organic synthesis. This salt consists of the tetrapropylammonium cation and the perruthenate anion, RuO−4.
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.
Gallium(III) bromide (GaBr3) is a chemical compound, and one of four gallium trihalides.
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.
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.
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.
Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane.
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.
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−.
1,2,4,5-Tetrabromobenzene is an aryl bromide and a four-substituted bromobenzene with the formula C6H2Br4. It is one of three isomers of tetrabromobenzene. The compound is a white solid. 1,2,4,5-Tetrabromobenzene is an important metabolite of the flame retardant hexabromobenzene.
Tetra-n-butylammonium iodide (TBAI) is a quaternary ammonium salt with an iodide counterion. It is used for synthesizing tetra-n-butylammonium triiodide by mixing with iodine.
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.
Thiophosphoryl bromide is an inorganic compound with the formula PSBr3.