426288

Tetrabutylammonium bromide

ACS reagent, ≥98.0%

• Synonym(s): N,N,N-tributyl-1-butanaminium bromide, TBAB, TBABr, tetra-n-butylammonium bromide
• Linear Formula: (CH₃CH₂CH₂CH₂)₄N(Br)
• CAS Number: 1643-19-2
• Molecular Weight: 322.37
• Beilstein/REAXYS Number: 3570983
• EC Number: 216-699-2
• MDL number: MFCD00011633
• UNSPSC Code: 12352100
• PubChem Substance ID: 24866693
• NACRES: NA.21

Properties

• grade: ACS reagent
• Quality Level: 200
• assay: ≥98.0%
• form: solid
• greener alternative product characteristics: Catalysis; Learn more about the Principles of Green Chemistry.
• impurities: ≤0.5% tributylamine hydrobromide; ≤0.5% tributylamine
• mp: 102-106 °C (lit.)
• 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

Description

General description

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

Safety Information

• pictograms: GHS07,GHS08
• signalword: Warning
• hcodes: H302 - H315 - H319 - H361fd - H412
• pcodes: P202 - P273 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• ppe: dust mask type N95 (US), Eyeshields, Gloves