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Triphenylphosphine

Triphenylphosphine

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Catalog Number

ACM603350-2

Product Name

Triphenylphosphine

Structure

CAS

603-35-0

Product Overview
Usage
Reviews

Synonyms

SCHEMBL1679860; triphenyl phophine; Trifenylfosfin; Triphenyl phosphine; Triphenylphosphine, ReagentPlus(R), 99%; 7817AH; Triphenyl phosphine pound>>Triphenyl phosphorous; Copolymer of styrene and divinylbenzene, diphenylphosphinated; Triphenylphosphine, ReagentPlus(R), >=98.5%;

IUPAC Name

triphenylphosphane;

Molecular Weight

262.292g/mol

Molecular Formula

C18H15P;(C6H5)3P;C18H15P;

Canonical SMILES

C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3;

InChI

InChI=1S/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H;

InChI Key

RIOQSEWOXXDEQQ-UHFFFAOYSA-N;

Melting Point

176 ° F (NTP, 1992);80.0°C;80.5 DEG C;80 °C;

Density

1.194 at 77 ° F (NTP, 1992);1.075 @ 80 DEG C/4 DEG C;1.1 g/cm3;

Solubility

Insoluble (NTP, 1992);FREELY SOL IN ETHER; SOL IN BENZENE, CHLOROFORM, GLACIAL ACETIC ACID; LESS SOL IN ALCOHOL; PRACTICALLY INSOL IN WATER;SOL IN CARBON TETRACHLORIDE;Solubility in water, mg/l at 25 °C: 0.09 (very poor);

Storage

Store at RT.

Color Form

MONOCLINIC PLATELETS OR PRISMS FROM ETHER;WHITE CRYSTALLINE SOLID;

Complexity

202

Covalently-Bonded Unit Count

EC Number

238-154-8

Exact Mass

262.091g/mol

Heavy Atom Count

ICSC Number

0700

Monoisotopic Mass

262.091g/mol

NSC Number

215203

Odor

ODORLESS;

Other Experimental

TRIBOLUMINESCENT;

Rotatable Bond Count

RTECS Number

SZ3500000

Topological Polar Surface Area

0A^2

UNII

26D26OA393

UN Number

3077

Vapor Pressure

Vapor pressure, Pa at 50 °C: 0.017;

Application

Triphenylphosphine serves multiple purposes across various fields. It is primarily used in organic synthesis, such as in the Wittig reaction, where it functions as a crucial reagent to produce alkenes. As a standard ligand in homogeneous catalysis, triphenylphosphine plays a vital role in facilitating reactions, including the hydroformylation of oils. Additionally, it acts as a stabilizer in the synthesis of rubbers and resins, as well as an antioxidant in polyvinyl chloride formulations. In the field of pharmaceuticals, triphenylphosphine contributes to the synthesis of Chlorambucil, a compound with cytotoxic effects on breast and pancreatic cancers, and in the preparation of α-Tocopherol analogues for monitoring antioxidant status. Furthermore, it is involved in the creation of organophosphorus pesticides through its role in the ester exchange method, producing intermediates like trimethyl phosphite. Triphenylphosphine also engages in other complex reactions, such as with hydrated ruthenium trichloride in methanol to yield specific ruthenium complexes, and it participates in the Heck reaction with 4-bromoanisole and ethyl acrylate in ionic liquids. Despite its wide range of applications, it is important to note that triphenylphosphine is reactive with oxidizing materials and is combustible, requiring careful handling.

January 12, 2025

A Versatile Catalyst for Efficient Synthesis

Triphenylphosphine from Alfa Chemistry is a remarkable asset in my research. Used it for Wittig synthesis and hydroformylation. Its stability and reactivity made a significant impact on my organophosphorus work results. Highly recommended!

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