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Sigma-Aldrich

Tetrabutylammonium bromide

ReagentPlus®, ≥99.0%

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Synonym(s):
TBAB
Linear Formula:
(CH3CH2CH2CH2)4N(Br)
CAS Number:
1643-19-2
Molecular Weight:
322.37
Beilstein/REAXYS Number:
3570983
EC Number:
216-699-2
MDL number:
MFCD00011633
UNSPSC Code:
12352111
PubChem Substance ID:
24851583
NACRES:
NA.21

Quality Level

300

product line

ReagentPlus®

assay

≥99.0%

form

powder, crystals or granules

pH

6.48 (30 °C)

mp

102-106 °C (lit.)

solubility

ethanol: 50 mg/mL, clear, colorless to light yellow

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 is a quaternary ammonium compound widely used as a phase transfer catalyst. TBAB decreases the retention time and removes 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 polymer synthesis. It participates as a catalyst during the solvent-free synthesis of biscoumarin and dihydropyrano[c]chromene derivatives.

Application

Tetrabutylammonium bromide may be used as a catalyst in the synthesis of following:
  • 1-cyano-2-thiophenylethane
  • 1-cyano-2-thiobutylethane
  • 1-cyano-2-(2-aminothiophenyl)ethane
  • methyl 3-thiophenylpropionate
  • methyl 3-thiobutylpropionate
  • methyl 2-methyl-3-thiophenylpropionate
  • methyl 2-methyl-3-thiobutylpropionate
  • diethyl 2-thiophenylsuccinate
  • diethyl 2-thiobutylsuccinate
  • 3-(4-chlorophenyl)-2-nitro-2-thiophenylpropane
  • 4-(4-chlorophenyl)-3-nitro-4-thiobutylbutane
  • 3-thiophenylcyclohexanone
  • 3-thioethylcyclohexanone
  • 4-methyl-4-thiophenylpentan-2-one
  • 4-methyl-4-thiobutylpentan-2-one
  • 4-thiophenylbutan-2-one
  • 4-thiobutylbutan-2-one
  • 3-thiophenylbutanal
  • 3-thiobutylbutanal

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

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

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Tetrabutylammonium bromide (TBAB): a neutral and efficient catalyst for the synthesis of biscoumarin and 3, 4-dihydropyrano [c] chromene derivatives in water and solvent-free conditions.
Khurana JM and Kumar S.
Tetrahedron Letters, 50(28), 4125-4127 (2009)
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)
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)
Direct polyamidation in molten tetrabutylammonium bromide: novel and efficient green media.
Mallakpour S and Yousefian H.
Polym. Bull., 60(2-3), 191-198 (2008)
Effect of analogue ions in normal-phase ion-pair chromatography of quaternary ammonium compounds.
Bluhm LH and Li T.
Journal of Chromatographic Science, 37(8), 273-276 (1999)
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