CAS 1530-32-1 Ethyltriphenylphosphonium bromide

Synonyms

Triphenylethylphosphonium bromide

IUPAC Name

ethyl(triphenyl)phosphanium;bromide

Molecular Weight

371.25

Molecular Formula

C20H20BrP

Canonical SMILES

CC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-];

InChI

JHYNXXDQQHTCHJ-UHFFFAOYSA-M

InChI Key

InChI=1S/C20H20P.BrH/c1-2-21(18-12-6-3-7-13-18,19-14-8-4-9-15-19)20-16-10-5-11-17-20;/h3-17H,2H2,1H3;1H/q+1;/p-1

Melting Point

203-205 °C(lit.)

Flash Point

200 °C

Purity

98%

Appearance

Solid

Storage

Store below +30°C.

Complexity

247

Covalently-Bonded Unit Count

EC Number

216-223-3

Exact Mass

370.049g/mol

H-Bond Acceptor

Heavy Atom Count

Isomeric SMILES

CC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]

Monoisotopic Mass

370.049g/mol

NSC Number

60660

Physical State

Off-white solid

Rotatable Bond Count

Topological Polar Surface Area

0A^2

UNII

R85V84UL5V

Application

Ethyltriphenylphosphonium bromide serves as a versatile chemical tool primarily used as a phase transfer catalyst to enhance the curing process of phenolic-based epoxy resins, fluoroelastomer resins, and thermosetting powder coatings. It aids in the synthesis of various organic compounds and acts as an intermediate in pharmaceuticals. In addition to its catalytic role, it participates in the synthesis of D-amino acids from L-cysteine-derived thiazolidines and is employed in aldol reactions as well as Horner-Wadsworth-Emmons olefination. Notably, it also facilitates the preparation of cycloalkanoindolines through diastereoselective intramolecular inimo-ene reactions. Ethyltriphenylphosphonium bromide finds application in the solid-state metathesis polycondensation to produce alkyl-dipropenylthiophene monomers, and it is involved in complex reactions like Mizoroki-Heck cyclization and cascading Tsuji-Trost cyclization processes. Additionally, it is recognized for its antiviral activity and functions as a Wittig reagent in chemical transformations.

February 3, 2025

Exceptional Catalyst for Research Applications

Ethyltriphenylphosphonium bromide from Alfa Chemistry has been invaluable in my research. As a phase transfer catalyst, it enhanced the Suzuki reaction and facilitated efficient synthesis of D-amino acids, elevating my lab's productivity and results.