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Merck

426288

Sigma-Aldrich

Tetrabutylammoniumbromid

greener alternative

ACS reagent, ≥98.0%

Synonym(e):

N,N,N-tributyl-1-butanaminium bromide, TBAB, TBABr, tetra-n-butylammonium bromide

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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:
12352100
PubChem Substanz-ID:
NACRES:
NA.21

Qualität

ACS reagent

Qualitätsniveau

Assay

≥98.0%

Form

solid

Grünere Alternativprodukt-Eigenschaften

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

Verunreinigungen

≤0.5% tributylamine hydrobromide
≤0.5% tributylamine

mp (Schmelzpunkt)

102-106 °C (lit.)

Grünere Alternativprodukt-Kategorie

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 (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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Anwendung

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

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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Chi Chen et al.
Nature communications, 13(1), 4935-4935 (2022-08-24)
Control over the copy number and nanoscale positioning of quantum dots (QDs) is critical to their application to functional nanomaterials design. However, the multiple non-specific binding sites intrinsic to the surface of QDs have prevented their fabrication into multi-QD assemblies
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)
Heat capacities and thermodynamic properties of two tetramethylammonium halides.
Chang SS and Westrum Jr EF.
J. Chem. Phys. , 36(9), 2420-2423 (1962)
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)
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)

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