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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 Registry Number 3570983

  •  EC Number 216-699-2

  •  MDL number MFCD00011633

  •  PubChem Substance ID 24866693

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Properties

Related Categories 12 Principles Aligned Products, Ammonium Salts, Chemical Synthesis, Essential Chemicals, Greener Alternative Products,
grade   ACS reagent
InChI Key   JRMUNVKIHCOMHV-UHFFFAOYSA-M
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.)

Description

Packaging

100 g in poly bottle

25 g in glass bottle

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

General description

Sigma Life Science is committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for energy efficiency. Find details here.

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.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
Flash Point(F) 
212 °F
Flash Point(C) 
100 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles
Peer-Reviewed Papers
15

References

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