Benzyltriethylammonium bromide Chemical Properties

Melting point:

193-195 °C (dec.) (lit.)

Density 

1.2838 (rough estimate)

refractive index 

1.5260 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Powder

color 

Off-white

Water Solubility 

soluble

Sensitive 

Hygroscopic

BRN 

3739113

CAS DataBase Reference

5197-95-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38-36/37/38

Safety Statements 

26-36-37/39

RIDADR 

UN 2811

WGK Germany 

3

F 

3-10

HS Code 

29239000

MSDS

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Benzyltriethylammonium bromide Usage And Synthesis

Description

Benzyltriethylammonium bromide is a versatile quaternary ammonium salt widely utilized in various chemical and industrial applications.

Chemical Properties

white to light yellow crystal powde

Uses

Benzyltriethylammonium bromide is recognized for its effectiveness as a phase transfer catalyst, facilitating the transfer of ions between immiscible phases, which enhances reaction rates in organic synthesis. Its ability to solubilize organic compounds in aqueous solutions makes it invaluable in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals. Researchers often leverage its properties in the preparation of quaternary ammonium compounds, surfactants, and as a reagent in organic reactions, such as alkylation and acylation processes.

Application

Benzyltriethylammonium bromide has been used in various applications, including:
Phase transfer catalysis: The compound has been employed as a phase transfer catalyst in organic synthesis reactions, facilitating the transfer of reactants between aqueous and organic phases.
Biomedical research: Benzyltriethylammonium bromide has been used as a selective inhibitor of certain enzymes, such as protein kinase C.
Pharmaceutical applications: The compound has been investigated as a potential excipient in pharmaceutical formulations, due to its ability to enhance the solubility and stability of certain drugs.

Synthesis

GENERAL METHOD: Benzyl halide (1 eq.) was dissolved in THF (50 mL/g benzyl halide) with reference to the method described in Ref. 4, to which 1.5 eq. of triethylamine (33 wt% ethanol solution) was subsequently added. The reaction mixture was stirred at room temperature for 24 h. The product precipitated as a white solid during the reaction. The resulting suspension was cooled to 0 °C, filtered, and the filter cake was washed with ice-cold ether and finally dried under vacuum to afford the target product benzyltriethylammonium bromide in a yield consistent with literature reports.

References

[1] Synlett, 2016, vol. 27, # 13, p. 1963 - 1968
[2] Journal of the American Chemical Society, 1980, vol. 102, # 21, p. 6463 - 6465
[3] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1715 - 1723
[4] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 9, p. 1881 - 1888
[5] Roczniki Chemii, 1965, vol. 39, p. 1223 - 1231

Benzyltriethylammonium bromide(5197-95-5)Related Product Information

• Benzyltriethylammonium chloride
• Tetrapropylammonium bromide
• Sodium bromate
• Benzyltributylammonium bromide
• Ethidium bromide
• Tetrabutylammonium bromide
• Tetraethylammonium bromide
• Ammonium bromide
• Rocuronium bromide
• Allyl bromide
• Triethylmethylammonium chloride
• Benzyltripropylammonium chloride
• BENZYL TRIFLUOROMETHYL SULFIDE
• Benzyltrimethylammonium tribromide
• BENZYLTRIMETHYLAMMONIUM DICHLOROIODATE
• Benzyltrimethylammonium chloride
• BENZYLTRIMETHYLAMMONIUM TETRACHLOROIODATE
• Benzyltrimethylammonium bromide