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Merck

193119

Sigma-Aldrich

Tetrabutylammoniumbromid

ReagentPlus®, ≥99.0%

Synonym(e):

TBAB

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About This Item

Lineare Formel:
(CH3CH2CH2CH2)4N(Br)
CAS-Nummer:
Molekulargewicht:
322.37
Beilstein:
3570983
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352111
PubChem Substanz-ID:
NACRES:
NA.21

Qualitätsniveau

Produktlinie

ReagentPlus®

Assay

≥99.0%

Form

powder, crystals or granules

pH-Wert

6.48 (30 °C)

mp (Schmelzpunkt)

102-106 °C (lit.)

Löslichkeit

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

InChIKey

JRMUNVKIHCOMHV-UHFFFAOYSA-M

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Allgemeine Beschreibung

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.

Anwendung

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

Rechtliche Hinweise

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

Piktogramme

Health hazardExclamation mark

Signalwort

Warning

Gefahreneinstufungen

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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Die Dokumentenbibliothek aufrufen

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)
Direct polyamidation in molten tetrabutylammonium bromide: novel and efficient green media.
Mallakpour S and Yousefian H.
Polym. Bull., 60(2-3), 191-198 (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)
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)
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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