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Tetrabutylammonium bromide

Tetrabutylammonium bromide, also known as tetrabutylammonium bromide. White crystal, deliquescence. 118 ℃ melting point. Soluble in water, alcohol, ether and acetone, slightly soluble in benzene.
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CAS:1643-19-2
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CAS:1643-19-2
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CAS:1643-19-2
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Products Intro: Product Name:Tetrabutylammonium bromide
CAS:1643-19-2

Tetrabutylammonium bromide manufacturers

  • Tetrabutylammonium bromide
  • $15.00-10.00 / KG
  • 2021-07-13
  • CAS:1643-19-2
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  • Supply Ability: Monthly supply of 1 ton

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Tetrabutylammonium bromide Chemical Properties
Melting point 102-106 °C(lit.)
Boiling point 102 °C
density 1.039 g/mL at 25 °C
refractive index n20/D 1.422
Fp 100℃
storage temp. Store below +30°C.
solubility H2O: 0.1 g/mL, clear, colorless
form Crystalline Powder
Specific Gravity1.007
color White to slightly cream
OdorAmine like
Water Solubility 600 g/L (20 ºC)
Sensitive Hygroscopic
λmaxλ: 240 nm Amax: 0.04
λ: 250 nm Amax: 0.03
λ: 260 nm Amax: 0.02
λ: 500 nm Amax: 0.02
BRN 3570983
Stability:Stable. Incompatible with strong oxidizing agents. Protect from moisture.
InChIKeyJRMUNVKIHCOMHV-UHFFFAOYSA-M
CAS DataBase Reference1643-19-2(CAS DataBase Reference)
NIST Chemistry ReferenceTetra-N-butylammonium bromide(1643-19-2)
EPA Substance Registry SystemTetrabutylammonium bromide (1643-19-2)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-22
Safety Statements 26-36-37/39
WGK Germany 3
3
Hazard Note Irritant
TSCA Yes
HS Code 29239000
MSDS Information
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Tetrabutylammonium bromide Usage And Synthesis
Physical and Chemical PropertiesTetrabutylammonium bromide, also known as tetrabutylammonium bromide. White crystal, deliquescence. 118 ℃ melting point. Soluble in water, alcohol, ether and acetone, slightly soluble in benzene.

Figure 1:  a structural formula of tetrabutylammonium bromide
Application(1) Used as a reagent for the analysis of organic synthesis.
(2) Tetrabutylammonium bromide is also an effective phase transfer catalyst.
Phase transfer catalyst, referred to as PTC, is able to transfer the aqueous phase (or organic phase) to the organic phase (or aqueous phase) catalyst, which can make the reaction between the aqueous phase and the organic phase of the catalyst. PTC has the function of changing the degree of ion solvation, increasing the activity of ion reaction, speeding up the reaction rate and so on. Solve the problem of the past in the two phases of the reaction is difficult to react.
Common quaternary ammonium salt phase transfer catalysts are: benzyl triethyl ammonium chloride, trioctyl methyl ammonium chloride, tetramethyl ammonium bromide, tetrapropylammonium chloride, tetrabutylammonium bromide , tetrabutyl ammonium iodide, benzyl triethyl ammonium bromide, triethyl hexyl bromide, octyl triethylammonium bromide.
Phase transfer catalyst is widely applied in organic synthesis: R2C for preparing compounds (carbene type compound), further preparation of the corresponding nitrile, isonitrile, Halon, dichloromethane cyclopropane derivatives, hydroxy acids and diazomethane. For the alkylation reaction, compared with traditional methods, to avoid the harsh conditions of dry operation, and high yield, it can also be used in the redox reaction, ester hydrolysis, substitution reaction, condensation reaction, addition reaction, polymerization reaction, addition reaction of carbon and the elimination of reaction and so on.
(3) For organic synthesis intermediates, phase transfer catalyst
(4) Ion-pairing reagents for the synthesis of bacampicillin, sultamicillin like.
(5) Ion pair chromatography reagents, phase transfer catalyst. Bacampicillin, sultamicillin like synthesis.
UsesTetrabutylammonium bromide (TBAB) is a quaternary ammonium compound. It is the most widely used phase transfer catalyst. Its interfacial properties have been studied in case of hydroxide initiated reactions. This may be applied in understanding the mechanism of phase transfer reactions. TBAB is reported to decrease retention time and remove peak tailing by acting as an ion pair reagent during the chromatographic analysis of quaternary ammonium compounds. In the molten state TBAB behaves like an ionic liquid which is a promising green alternative to organic solvents in organic synthesis. Its molar heat capacity, entropy and free energy function have been determined.
Recently, molten tetrabutylammonium bromide (TBAB) was used as a low toxic and cost-effective IL in a number of constructive synthetic transformations.
Tetrabutylammonium bromide (TBAB) may be used in the molten state in the following processes:
Synthesis of (2S)-5-(3-phenyl-2-phthalimidylpropanoylamino)isophthalic acid.
Synthesis of alkyl-substituted pyrroles in the absence of catalyst and organic solvent.
Synthesis of dithioacetals from acetals by transthioacetalisation in a solvent free environment.
Synthesis of polyamides (PAs) by the polymerization of terephthalic acid and diisocyanates.
Catalyze the addition of thiols to conjugated alkenes.
Dehydrochlorination of poly(vinyl chloride).
preparationPreparative Methods: several methods are available to recover the quaternary ammonium ion efficiently.Prepared by reaction of tri-n-butylamine and n-butyl bromide.
ToxicityThe acute oral LD50 (mouse): 590mg/kg. Inhalation, ingestion and skin contact toxic to the skin, eyes and respiratory system irritation.
More information from the ChemicalBook Xiaonan editor (2015-09-16).
Chemical Propertieswhite crystals or powder
UsesPTC catalyst
DefinitionChEBI: A tetrabutylammonium salt with bromide as the anionic counterpart.
Purification MethodsCrystallise the salt from *benzene (5mL/g) at 80o by adding hot n-hexane (three volumes) and allowing to cool. Dry it over P2O5 or Mg(ClO4)2, under vacuum. The salt is very hygroscopic. It can also be crystallised from ethyl acetate or dry acetone by adding diethyl ether and dried in vacuo at 60o for 2 days. It has been crystallised from acetone by addition of diethyl ether. It is so hygroscopic that all manipulations should be carried out in a dry-box. It has been purified by precipitation from a saturated solution in dry CCl4 on addition of cyclohexane or by recrystallisation from ethyl acetate, then heating in vacuum to 75o in the presence of P2O5. [Symons et al. J Chem Soc, Faraday Trans 1 76 2251 1908.] It also recrystallises from CH2Cl2/diethyl ether and is dried in a vacuum desiccator over P2O5. [Blau & Espenson J Am Chem Soc 108 1962 1986, Beilstein 4 IV 657.]
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