Tetrapropylammonium bromide
[CAS# 1941-30-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: Tetrapropylammonium bromide
• Synonyms: TPABr
• Molecular Formula: C₁₂H₂₈N.Br
• Molecular Weight: 266.26
• CAS Registry Number: 1941-30-6
• EC Number: 217-727-6
• SMILES: CCC[N+](CCC)(CCC)CCC.[Br-]

Properties

• Melting point: 270 °C (decomp.) (Expl.)
• Water solubility: 100 g/L

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovery and Applications

Tetrapropylammonium bromide (C12H28NBr) is a quaternary ammonium salt consisting of a tetrapropylammonium cation (C3H7)4N+ and a bromide anion (Br−). It is typically synthesized through the reaction of propylamine with 1-bromopropane. This compound is a colorless to pale yellow liquid that is soluble in polar organic solvents such as water, alcohols, and acetone.

Tetrapropylammonium bromide is primarily used as a phase-transfer catalyst in organic synthesis. In phase-transfer catalysis, it facilitates the migration of anions from an aqueous phase to an organic phase, thereby increasing the reactivity of certain reactions that involve immiscible solvents. This property is particularly valuable in nucleophilic substitution reactions, where it enhances the efficiency of reactions between reagents in different phases. Tetrapropylammonium bromide has been employed in various industrial and laboratory processes to accelerate reactions such as the alkylation of phenols and the synthesis of ethers.

In addition to its use in phase-transfer catalysis, tetrapropylammonium bromide has been utilized in the synthesis of other organic compounds and materials. It is involved in the preparation of surfactants, polymerization catalysts, and in the formation of ionic liquids, which have applications in electrochemical systems, including batteries and capacitors.

Tetrapropylammonium bromide is also used in the preparation of other quaternary ammonium salts with specific applications in catalysis and as an intermediary in chemical synthesis. Its properties, such as solubility and its ability to facilitate the transfer of ions, make it an effective reagent in these applications.

In conclusion, tetrapropylammonium bromide is an important chemical compound with applications in organic synthesis, particularly as a phase-transfer catalyst. It plays a significant role in improving reaction rates and facilitating the efficient transfer of reactants between different phases. Its versatility in chemical synthesis makes it a valuable tool in various research and industrial applications.

References

2024. Facile synthesis of hierarchical H-[B]-ZSM-5 aggregates via design-optimized desilication for enhanced methanol-to-propylene conversion. Research on Chemical Intermediates.
DOI: 10.1007/s11164-024-05399-y

2024. Template-Free Synthesis of ZSM-5: Effect of Precursor Composition on the Crystallinity and Crystal Morphology. Petroleum Chemistry, 64(9).
DOI: 10.1134/s0965544124060033

2013. Synthesis and catalytic applications of hierarchical mesoporous AlPO/ZnAlPO for direct hydroxylation of benzene to phenol using hydrogen peroxide. Journal of Materials Chemistry A, 1(11).
DOI: 10.1039/c3ta00113j