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1643-19-2

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Identification

Name
Tetrabutylammonium bromide
CAS
1643-19-2
Synonyms
ALIQUAT(R) 100
IPC-TBA-BR
TBAB
TETRABUTYLAMMONIUM BROMIDE
TETRABUTYLAMMONIUM BROMIDE SOLUTION
TETRA-N-BUTYLAMMONIUM BROMIDE
1-Butanaminium, N,N,N-tributyl-, bromide
1-Butanaminium,N,N,N-tributyl-,bromide
n,n,n-tributyl-1-butanaminiubromide
Tetrbutyl Ammonium Bromide
TETRABUTYL AMONIUM BROMIDE
4-BUTYLBENZALDEHYDE DIETHYL ACETAL, TECH ., 90%
TETRABUTYLAMMONIUM BROMIDE SOLUTION, ~50% IN WATER
TETRABUTYLAMMONIUM BROMIDE, ELECTRO-CHEM ICAL GRADE
TETRABUTYLAMMONIUM BROMIDE, 98+%, A.C.S. REAGENT
TETRABUTYLAMMONIUM BROMIDE, FOR IPC
Tetrabutylammonium bromide 50 %
TETRABUTYLAMMONIUM BROMIDE REAGENTPLUS&
TETRABUTYLAMMONIUM BROMIDE CONC., FOR
TETRABUTYLAMMONIUM BROMIDE, 50 WT. % SOL UTION IN WATER
EINECS(EC#)
216-699-2
Molecular Formula
C16H36BrN
MDL Number
MFCD00011633
Molecular Weight
322.37
MOL File
1643-19-2.mol

Chemical Properties

Appearance
white crystals or powder
mp 
102-106 °C(lit.)

bp 
102 °C
density 
1.039 g/mL at 25 °C
refractive index 
n20/D 1.422
storage temp. 
Store at RT.
solubility 
H2O: 0.1 g/mL, clear, colorless

Stability:
Stable. Incompatible with strong oxidizing agents. Protect from moisture.
Water Solubility 
600 g/L (20 ºC)
Sensitive 
Hygroscopic
Detection Methods
T,NMR
BRN 
3570983
CAS DataBase Reference
1643-19-2(CAS DataBase Reference)
NIST Chemistry Reference
Tetra-N-butylammonium bromide(1643-19-2)
EPA Substance Registry System
1643-19-2(EPA Substance)

Safety Data

Hazard Codes 
Xi,Xn
Risk Statements 
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed.
Safety Statements 
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
WGK Germany 
3


3
Hazard Note 
Irritant
HS Code 
29239000

Raw materials And Preparation Products

Material Safety Data Sheet(MSDS)

Questions And Answer

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.
Uses
Tetrabutylammonium 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).
preparation
Preparative Methods: several methods are available to recover the quaternary ammonium ion efficiently.Prepared by reaction of tri-n-butylamine and n-butyl bromide.
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).

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