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426288 Sigma-Aldrich

Tetrabutylammonium bromide

Green Alternative

ACS reagent, ≥98.0%

  • CAS Number 1643-19-2

  • Linear Formula (CH3CH2CH2CH2)4N(Br)

  • Molecular Weight 322.37

  •  Beilstein/REAXYS Number 3570983

  •  EC Number 216-699-2

  •  MDL number MFCD00011633

  •  PubChem Substance ID 24866693

  •  NACRES NA.21

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Properties

Related Categories 12 Principles Aligned Products, Ammonium Salts, Chemical Synthesis, Chemicals for the synthesis of candidate COVID-19 treatments, Essential Chemicals,
Quality Level   200
grade   ACS reagent
assay   ≥98.0%
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

Packaging

100 g in poly bottle

25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
WarningDanger
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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