25361-69-7

Usage

Uses

Used in Organic Chemistry:
(2-Ethoxyethyl)triphenylphosphonium bromide is used as a phase-transfer catalyst for facilitating the transfer of organic molecules between immiscible phases. This makes it a valuable tool in various synthetic processes such as nucleophilic substitutions and alkylations.
Used in Laboratory and Industrial Settings:
Due to its versatile and important role in organic synthesis, (2-Ethoxyethyl)triphenylphosphonium bromide is widely used in both laboratory and industrial settings for a range of chemical reactions and processes.

InChI:InChI=1/C22H24OP/c1-2-23-18-19-24(20-12-6-3-7-13-20,21-14-8-4-9-15-21)22-16-10-5-11-17-22/h3-17H,2,18-19H2,1H3/q+1

Upstream product

• 64-17-5 ethanol 
• 592-55-2 2-Bromoethyl ethyl ether 
• 603-35-0 triphenylphosphine 
• 7237-34-5 2-(hydroxyethyl)triphenylphosphonium bromide 
• 141-52-6 sodium ethanolate 
• 22409-83-2 (2-phenoxyethyl)triphenylphosphonium bromide 

Downstream Products

• 111088-66-5 (S)-3-{4-[4-Benzenesulfonyloxy-3-((E)-3-ethoxy-propenyl)-phenoxy]-3,5-diiodo-phenyl}-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester 

Relevant academic research and scientific papers

SUBSTITUTED BICYCLIC COMPOUNDS

Disclosed are compounds of Formulas (I), (II), (III), (IV), and (V) and/or a salt thereof, wherein R1 is OH or OP(O)(OH)2, and X1, X2, X3, R2, R2a, Ra, Rb, and Rc are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

ALKALINE HYDROLYSIS OF β AND γ-FUNCTIONAL PHOSPHONIUM SALTS

A model study of alkaline hydrolysis of β- and γ-heterosubstituted phosphonium salts has been made and used as a synthetic method to obtain diphosphine dioxides affording additional coordination sites in an alkyl chain linked to phosphorus.After synthesis of the corresponding salts, anomalous fragmentations, such as inversion in cleavage selectivity or participation of the reaction solvent, have been pointed out in alkaline hydrolysis of β-functional phosphonium salts.A mechanism is suggested to account for the presence of all compounds detected.In the case of γ-functional phosphonium salts, the alkaline hydrolysis leads only to predicted compounds corresponding to the usual selective cleavage of one phenyl group.The results observed have been used to synthesize symmetric and asymmetric diphosphine dioxides with ether substituted side chains. - Key words: Phosphonium salt, phosphine oxide, diphosphine dioxides, alkaline hydrolysis, cleavage, mechanism.

Thyroid Hormone Analogues. Synthesis of 3'-Substituted 3,5-Diiodo-L-thyronines and Quantitative Structure-Activity Studies of in Vivo Thyromimetic Activities in Rat Liver and Heart

Twenty-nine 3'-substituted derivatives of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3) have been synthesized by using established methods and by new route involving manipulation of a 3'-formyl intermediate.In vitro hormone receptor binding (to intact nuclei) and in vivo thyromimetic activity (induction of mitochondrial 3-phosphoglycerate oxidoreductase, GPDH) were measured in rat liver and heart for these new analogues and for the 18 previously reported 3'-substituted 3,5-diiodo-L-thyronines.Analysis of the binding data using theoretical conformational and quantitative structure-affinity methods implies that the 3'-substituent recognition site on the thyroid hormone receptor is hydrophobic and limited in depth to the length of the natural iodo substituent, but has sufficient width to accomodate a phenyl or cyclohexyl group.Receptor binding is reduced by approximately 10-fold in 3'-acyl derivatives which form strong intramolecular acceptor hydrogen bonds with the ajacent 4'-hydroxyl.The compounds studied showed no differences in their relative affinities for heart and liver nuclei, suggesting that receptors in these tissues are similar.However, the relationships between thyromimetic activity (induction of GPDH) and nuclear binding showed some tissue differences.A high correlation between activity and binding is observed for full agonists in the heart, but an equally significant correlation for the liver data is only seen when 3'-substituent bulk (molar reactivity) is included in the analysis.These results suggest the possibility that differential tissue penetration or access to receptors may occur in vivo.

SYNTHESE DE SELS DE VINYLPHOSPHONIUMS β-SUBSTITUES ET DE SELS D'ALKYLPHOSPHONIUMS β-DISUBSTITUES

Vinylene-1,2 bisphosphoniums salts react, in the presence of a base, with compounds ZH having a mobile hydrogen, to give a way of sysnhesis of β-substituted vinylphosphoniums salts 2 or β-disubstituted alkylphosphoniums salts 3.We have studied the limits of these synthesis depending on the experimental conditions and the nature of compounds ZH (alcohols, phenols, thiols, phosphines, amines).