Ethyltriphenylphosphonium bromide CAS Number: 1530-32-1

Chemical Properties

White to off-white crystalline powder

Uses

suzuki reaction

Uses

PTC catalyst

Uses

Ethyltriphenylphosphonium Bromide is used as a wittig reagent. Ethyltriphenylphosphonium Bromide and other phosphonium salts show antiviral activity.

Uses

Ethyltriphenylphosphonium Bromide (ETPB) is a phase transfer catalyst, used to accelerate the cure of phenolic-based epoxy resins, certain fluoroelastomer resins and thermosetting powder coatings. It is also used as catalysts in the synthesis of certain organic compounds and as a pharmaceutical intermediate.

1. Ethyltriphenylphosphonium bromide acts as a reactant in the synthesis of D-amino acids from L-cysteine-derived thiazolidines, Leiodolide A through aldol reactions and Horner-Wadsworth-Emmons olefination.
2. It is also used in the preparation of cycloalkanoindolines through diastereoselective intramolecular inimo-ene reactions.
3. it is used as a reagent in solid-state metathesis polycondensation to prepare alkyl-dipropenylthiophene monomers.
4. Mizoroki-Heck cyclization and cascading Tsuji-Trost cyclization reactions.

Flammability and Explosibility

Not classified

reaction suitability

reaction type: C-C Bond Formation

Synthesis

74-96-4

603-35-0

1530-32-1

In a 1500 mL three-necked flask, 54 g (0.5 mol) of ethyl bromide, 210 g (0.8 mol) of triphenylphosphine and 1000 mL of toluene were added sequentially. A reflux condenser tube was installed, magnetic stirring was turned on and the reaction was heated to reflux state and kept at reflux for 10 hours. Upon completion of the reaction, the reaction system was naturally cooled to 50 °C and a large amount of white solid was observed to precipitate. The solid product was collected by filtration through a Brinell funnel and the filter cake was washed with toluene three times (50 mL each time). The resulting solid was transferred to a vacuum drying oven and dried at 50 °C until constant weight, resulting in 170.4 g of ethyltriphenylphosphonium bromide in 91.8% yield.

Purification Methods

Recrystallise it from H2O and dry it in high vacuum at 100o. IR has bands at 1449, 1431 and 997cm-1 . [Wittig & Wittenberg Justus Liebigs Ann Chem 606 1 1957, Bergmann & Dusza J Org Chem 23 1245 1958, Beilstein 16 IV 982.]

References

[1] Journal of Fluorine Chemistry, 2002, vol. 113, # 2, p. 177 – 183
[2] Pharmazie, 1999, vol. 54, # 1, p. 26 – 30
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1989, vol. <2> 38, # 12, p. 2553 – 2556
[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, vol. <2> 38, # 12, p. 2789 – 2792
[5] Journal of the American Chemical Society, 1980, vol. 102, p. 2437