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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
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Product Name

Tetrabutylammonium bromide, ReagentPlus®, ≥99.0%

Quality Level

300

product line

ReagentPlus®

assay

≥99.0%

form

powder, crystals or granules

reaction suitability

core: ammonium

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

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

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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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

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signalword

Warning

pictograms

Health hazardExclamation mark
GHS08,GHS07

Hazard Classifications

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

Storage Class

11 - Combustible Solids

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBH1653V
BCCC7728
BCCF9817
BCCF4936
BCCD5644

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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)
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)
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)
View All Related Papers

Global Trade Item Number

SKUGTIN
193119-100G04061835320332
193119-25G04061835320349
193119-25KG04061833636435
193119-500G04061838760661
193119-5KG04061838760678