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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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Tetrabutylammonium bromide Basic information

Product Name:
Tetrabutylammonium bromide
CAS:
1643-19-2
MF:
C16H36BrN
MW:
322.37
EINECS:
216-699-2
Mol File:
1643-19-2.mol
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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
Flash point:
100℃
storage temp. 
Store at RT.
solubility 
H2O: 0.1 g/mL, clear, colorless
form 
Crystalline Powder
color 
White to slightly cream
Specific Gravity
1.007
Odor
Amine like
Water Solubility 
600 g/L (20 ºC)
λmax
λ: 240 nm Amax: 0.04
λ: 250 nm Amax: 0.03
λ: 260 nm Amax: 0.02
λ: 500 nm Amax: 0.02
Sensitive 
Hygroscopic
BRN 
3570983
Stability:
Stable. Incompatible with strong oxidizing agents. Protect from moisture.
InChIKey
JRMUNVKIHCOMHV-UHFFFAOYSA-M
CAS DataBase Reference
1643-19-2(CAS DataBase Reference)
NIST Chemistry Reference
Tetra-N-butylammonium bromide(1643-19-2)
EPA Substance Registry System
Tetrabutylammonium bromide (1643-19-2)
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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

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Tetrabutylammonium bromide Usage And Synthesis

Physical and Chemical Properties

Tetrabutylammonium 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.

Toxicity

The 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 Properties

white crystals or powder

Uses

PTC catalyst 

Definition

ChEBI: A tetrabutylammonium salt with bromide as the anionic counterpart.

Purification Methods

Crystallise 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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