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426288

Sigma-Aldrich

Tetrabutylammonium bromide

greener alternative

ACS reagent, ≥98.0%

Linear Formula:
(CH3CH2CH2CH2)4N(Br)
CAS Number:
Molecular Weight:
322.37
Beilstein:
3570983
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

grade

ACS reagent

assay

≥98.0%

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.)

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

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

Packaging

100 g in poly bottle
25 g in glass bottle

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Heat capacities and thermodynamic properties of two tetramethylammonium halides.
Chang SS and Westrum Jr EF.
J. Chem. Phys. , 36(9), 2420-2423 (1962)
Silvia Ghimenti et al.
Scientific reports, 10(1), 7441-7441 (2020-05-06)
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Novel biobased polyurethanes synthesized from nontoxic phenolic diol containing l-tyrosine moiety under green media.
Mallakpour S, et al.
Journal of Polymers and the Environment, 18(4), 685-695 (2010)
Catalysis by ionic liquids: solvent-free efficient transthioacetalisation of acetals by molten tetrabutylammonium bromide.
Ranu BC, et al.
Journal of the Chemical Society. Perkin Transactions 1, 13, 1520-1522 (2002)
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)

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