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Sigma-Aldrich

Tetrabutylammonium bromide

greener alternative

ACS reagent, ≥98.0%

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Synonym(s):
N,N,N-tributyl-1-butanaminium bromide, TBAB, TBABr, tetra-n-butylammonium bromide
Linear Formula:
(CH3CH2CH2CH2)4N(Br)
CAS Number:
1643-19-2
Molecular Weight:
322.37
Beilstein:
3570983
EC Number:
216-699-2
MDL number:
MFCD00011633
PubChem Substance ID:
24866693
NACRES:
NA.21

grade

ACS reagent

Quality Level

200

Assay

≥98.0%

form

solid

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

impurities

≤0.5% tributylamine hydrobromide
≤0.5% tributylamine

mp

102-106 °C (lit.)

greener alternative category

SMILES string

[Br-].CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/C16H36N.BrH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1

InChI key

JRMUNVKIHCOMHV-UHFFFAOYSA-M

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General description

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.
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Application

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).
Used with phosphorus pentoxide for greener deoxybromination.
Used with phosphorus pentoxide for greener deoxybromination.
Process for Producing Halogenated Heteroaryl Compounds

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Chi Chen et al.
Nature communications, 13(1), 4935-4935 (2022-08-24)
Control over the copy number and nanoscale positioning of quantum dots (QDs) is critical to their application to functional nanomaterials design. However, the multiple non-specific binding sites intrinsic to the surface of QDs have prevented their fabrication into multi-QD assemblies
Dehydrochlorination of poly (vinyl chloride) by aqueous sodium hydroxide solution under two-phase conditions.
Kise H.
Journal of Polymer Science Part A: Polymer Chemistry, 20(11), 3189-3197 (1982)
Silvia Ghimenti et al.
Scientific reports, 10(1), 7441-7441 (2020-05-06)
Heart failure (HF) is a cardiovascular disease affecting about 26 million people worldwide costing about $100 billons per year. HF activates several compensatory mechanisms and neurohormonal systems, so we hypothesized that the concomitant monitoring of a panel of potential biomarkers
Heat capacities and thermodynamic properties of two tetramethylammonium halides.
Chang SS and Westrum Jr EF.
J. Chem. Phys. , 36(9), 2420-2423 (1962)
Interfacial chemistry behavior of phase transfer catalysis for hydroxide ion initiated reactions.
Xia L, et al.
Colloids and Surfaces. A, Physicochemical and Engineering Aspects, 317(1), 747-750 (2008)
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