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Merck

193119

Tetrabutylammonium bromide

greener alternative

≥99.0%, powder, crystals or granules, ReagentPlus®

Synonym(s):

TBAB

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(Br)
CAS Number:
1643-19-2
Molecular Weight:
322.37
NACRES:
NA.21
PubChem Substance ID:
24851583
UNSPSC Code:
12352111
EC Number:
216-699-2
MDL number:
MFCD00011633
Beilstein/REAXYS Number:
3570983
assay:
≥99.0%
form:
powder, crystals or granules
solubility:
ethanol: 50 mg/mL, clear, colorless to light yellow

Product Name

Tetrabutylammonium bromide, ReagentPlus®, ≥99.0%

InChI key

JRMUNVKIHCOMHV-UHFFFAOYSA-M

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

SMILES string

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

product line

ReagentPlus®

assay

≥99.0%

form

powder, crystals or granules

greener alternative product characteristics

Catalysis
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pH

6.48 (30 °C)

mp

102-106 °C (lit.)

solubility

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

functional group

amine

greener alternative category

Aligned

Quality Level

300

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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

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.
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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

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN9122
BCCN5435
BCCN5434
BCCK6775
BCCM5355

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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)
Catalysis by an ionic liquid: efficient conjugate addition of thiols to electron deficient alkenes catalyzed by molten tetrabutylammonium bromide under solvent-free conditions.
Ranu BC, et al.
Tetrahedron, 59(14), 2417-2421 (2003)
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