10089-43-7

Usage

Uses

Used in Organic Synthesis:
Tris(4-methylphenyl)phosphane selenide is utilized as a reagent for the formation of carbon-phosphorus and carbon-selenium bonds, which is crucial in the development of new organic molecules and materials. Its unique structure and reactivity facilitate the synthesis of complex organic compounds that may have various applications in pharmaceuticals, materials science, and other fields.
Used in Catalysis:
tris(4-methylphenyl)phosphane selenide has been studied for its potential applications in catalysis, where it could serve as a catalyst or a catalyst precursor to enhance the efficiency of chemical reactions. Its ability to form and break bonds selectively can be harnessed to improve reaction yields and selectivity in various catalytic processes.
Used in Semiconductor Material Precursor:
Tris(4-methylphenyl)phosphane selenide is also considered as a precursor for semiconductor materials. Given the importance of phosphorus and selenium in the semiconductor industry, tris(4-methylphenyl)phosphane selenide could be a key component in the development of new semiconductor materials with improved electronic properties, contributing to advancements in electronics and optoelectronics.

Upstream product

• 1038-95-5 Tri(p-tolyl)phosphine 
• 106-38-7 para-bromotoluene 

Downstream Products

• 85543-81-3 (ZnI₂PSe(C₆H₄CH₃)3)2 
• 85543-84-6 (HgCl₂PSe(C₆H₄CH₃)3)2 
• 85543-85-7 (HgBr₂PSe(C₆H₄CH₃)3)2 
• 85543-86-8 (HgI₂PSe(C₆H₄CH₃)3)2 
• 85543-83-5 (CdI₂PSe(C₆H₄CH₃)3)2 

Relevant academic research and scientific papers

Palladium-Catalyzed Cross-Coupling of Silyl Electrophiles with Alkylzinc Halides: A Silyl-Negishi Reaction

We report the first example of a silyl-Negishi reaction between secondary zinc organometallics and silicon electrophiles. This palladium-catalyzed process provides direct access to alkyl silanes. The delicate balance of steric and electronic parameters of the employed DrewPhos ligand is paramount to suppressing isomerization and promoting efficient and selective cross-coupling.

Photoinduced Synthesis of P-Perfluoroalkylated Phosphines from Triarylphosphines and Their Application in the Copper-Free Cross-Coupling of Acid Chlorides and Terminal Alkynes

A practical synthesis yielding P-perfluoroalkylated phosphines from triarylphosphines and perfluoroalkyl iodides has been developed. The photoinduced reaction involves the substitution of aryl groups on the phosphorus atom with perfluoroalkyl groups to successfully afford P-perfluoroalkylated phosphines. In addition, the P-perfluoroalkylated phosphines were found to promote the Cu-free cross-coupling reaction of acid chlorides with terminal alkynes.

Rapid phosphorus(III) ligand evaluation utilising potassium selenocyanate

Oxidative addition of SeCN- to tertiary phosphine ligands has been investigated in methanol at 298 K by use of UV-Vis stopped-flow and conventional spectrophotometry. In most cases kobsvs. [SeCN -] plots were linear with zero intercepts corresponding to a rate expression of kobs = k1[SeCN-]. Reactions rates are dependent on the electron density of the phosphorus centre with k 1 varying by five orders of magnitude from 1.34 ± 0.02 × 10-3 to 51 ± 3 mol-1 dm3 s-1 for P(2-OMe-C6H4)3 to PCy3 respectively. Activation parameters range from 27 ± 1 to 49.0 ± 1.3 kJ mol-1 for ΔH? and -112 ± 9 to -140 ± 3 J K-1 mol-1 for ΔS ? supporting a SN2 mechanism in which the initial nucleophilic attack of P on Se is rate determining. Reaction rates are promoted by more polar solvents supporting the mechanistic assignment. Reasonable linear correlations were observed between log k1vs. pKa, 1JP-Se and χd values of the phosphines. The reaction rates are remarkably sensitive to the steric bulk of the substituents, and substitution of phenyl rings in the 2 position resulted in a decrease in the reaction rate. The crystal structures of SePPh2Cy and SePPhCy2 have been determined displaying Se-P bond distances of 2.111(2) and 2.1260(8) respectively. The Royal Society of Chemistry 2008.

STERIC AND ELECTRONIC DESTABILIZATION OF THE P-Se BOND IN TRIARYLPHOSPHINE SELENIDE SYSTEMS

Electronic and steric effects in SeP(Ar)3 compounds are discussed with the assistance of 1J(77Se-31P) correlations with d(P-Se) values and the pKa of the arylphosphines.