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Sigma-Aldrich

Tetrabutylammonium bromide

greener alternative

ACS reagent, ≥98.0%

Synonyme(s) :

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

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About This Item

Formule linéaire :
(CH3CH2CH2CH2)4N(Br)
Numéro CAS:
Poids moléculaire :
322.37
Numéro Beilstein :
3570983
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352100
ID de substance PubChem :
Nomenclature NACRES :
NA.21

Qualité

ACS reagent

Niveau de qualité

Pureté

≥98.0%

Forme

solid

Caractéristiques du produit alternatif plus écologique

Catalysis
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sustainability

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Impuretés

≤0.5% tributylamine hydrobromide
≤0.5% tributylamine

Pf

102-106 °C (lit.)

Autre catégorie plus écologique

Chaîne SMILES 

[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

Clé InChI

JRMUNVKIHCOMHV-UHFFFAOYSA-M

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Description générale

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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Application

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

Pictogrammes

Health hazardExclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves


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Consulter la Bibliothèque de documents

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
Heat capacities and thermodynamic properties of two tetramethylammonium halides.
Chang SS and Westrum Jr EF.
J. Chem. Phys. , 36(9), 2420-2423 (1962)
Silvia Ghimenti et al.
Scientific reports, 10(1), 7441-7441 (2020-05-06)
Heart failure (HF) is a cardiovascular disease affecting about 26 million people worldwide costing about $100 billons per year. HF activates several compensatory mechanisms and neurohormonal systems, so we hypothesized that the concomitant monitoring of a panel of potential biomarkers
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)
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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