Verification code

Benzyltriphenylphosphonium bromide

Catalog Number
ACM1449463-2
Product Name
Benzyltriphenylphosphonium bromide
Structure
CAS
1449-46-3
Category
Quaternary Phosphonium Compounds; Chemical Intermediate
Synonyms
(Phenylmethyl)triphenylphosphonium bromide
IUPAC Name
benzyl(triphenyl)phosphanium;bromide;
Molecular Weight
433.32
Molecular Formula
C25H22PBr
Canonical SMILES
C1=CC=C(C=C1)C[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Br-];
InChI
InChI=1S/C25H22P.BrH/c1-5-13-22(14-6-1)21-26(23-15-7-2-8-16-23,24-17-9-3-10-18-24)25-19-11-4-12-20-25;/h1-20H,21H2;1H/q+1;/p-1;
InChI Key
WTEPWWCRWNCUNA-UHFFFAOYSA-M;
Purity
99%
Active Content
95%
Physical State
Off-white solid
Topological Polar Surface Area
0A^2

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Case Study

Benzyltriphenylphosphonium Bromide as a Phase Transfer Catalyst in the Wittig Reaction for Stilbene Synthesis

Wang, Maw-Ling, Shaw-Rong Lay, and Jing-Jer Jwo. Journal of the Chinese Institute of Engineers 12.3 (1989): 293-300.

Benzyl Triphenyl Phosphonium Bromide as a High-Efficiency Corrosion Inhibitor for Mild Steel in Sulfuric Acid Media

Bhrara, Kalpana, and Gurmeet Singh. Applied Surface Science 253.2 (2006): 846-853.

Benzyl triphenyl phosphonium bromide (BTPPB) has been evaluated as an effective corrosion inhibitor for mild steel in aerated 0.5 M H2SO4. Using galvanostatic and potentiostatic polarization methods, the inhibitory performance of BTPPB was investigated across varying concentrations (10⁻²-10⁻⁷ M) and temperatures (298-338 K). The studies revealed that inhibition efficiency increases with concentration, achieving up to 99.3% at 10⁻² M, indicating strong adsorption on the steel surface.
BTPPB was synthesized via the reaction of triphenylphosphine with benzyl bromide, purified, and characterized using FTIR spectroscopy. Electrochemical results demonstrated significant reduction in corrosion current, while the effective activation energy and heat of adsorption were determined to elucidate the adsorption mechanism. Surface characterization via scanning electron microscopy (SEM) confirmed the formation of a protective inhibitor layer, corroborating the electrochemical findings. Quantum chemical calculations, including PM3 and further optimization using HyperChem, provided insight into molecular geometry and electron distribution, supporting the proposed adsorption model.
FTIR analysis suggested that adsorption occurs through interactions between the phosphonium group and the mild steel surface, forming a stable protective film. The combination of electrochemical, spectroscopic, and computational data demonstrates that BTPPB effectively inhibits both anodic and cathodic corrosion processes, highlighting its potential as a high-performance corrosion inhibitor in acidic industrial environments.
This study establishes BTPPB as a reliable chemical additive for corrosion protection, providing a mechanistic understanding that can guide its practical application in metal protection and industrial acid systems.

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