CAS 14694-95-2 Tris(triphenylphosphine)rhodium(I) chloride

Synonyms

Chlorotris-(triphenylphosphino)-rhodium

IUPAC Name

rhodium;triphenylphosphane;chloride;

Molecular Weight

925.21

Molecular Formula

C54H45ClP3Rh

Canonical SMILES

C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh]

InChI

InChI=1S/3C18H15P.ClH.Rh/c3*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h3*1-15H;1H;/p-1

InChI Key

QBERHIJABFXGRZ-UHFFFAOYSA-M

Melting Point

245-250 °C

Purity

98%

Appearance

Magenta crystal

Storage

2-8°C

Complexity

202

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

EC Number

238-744-5

Exact Mass

924.14776

Formal Charge

-1

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

924.14776

Rotatable Bond Count

Topological Polar Surface Area

0 Å²

UNII

0FV534BKEV

Application

Tris(triphenylphosphine)rhodium(I) chloride, also known as Wilkinson's catalyst, serves a versatile role in organic synthesis due to its effectiveness as a homogeneous hydrogenation catalyst that operates under mild conditions. This compound, recognized for its magenta crystals, is primarily utilized to catalyze the hydrogenation of alkenes. Beyond hydrogenation, it proves essential in the catalytic hydroboration of alkenes when combined with catecholborane and pinacolborane, as well as in the selective 1,4-reduction of α, β-unsaturated carbonyl compounds. The catalyst is instrumental in the decarbonylation of aldehydes and supports regio- and stereoselective allylic substitution reactions, enhancing its utility in complex organic transformations. It also facilitates alkyne hydro-phosphorylation, Heck-type reactions with α,β-unsaturated esters, and alkyne arylation. Moreover, it aids in allylic alcohol-olefin coupling, the formation of terminal alkenes from ketones, and the Rh-catalyzed isomerization of α-aryl propargyl alcohols to indanones, while also enabling the reductive deprotection of silyl groups.

February 19, 2025

Exceptional Catalyst with Versatile Applications

I used Alfa Chemistry's Tris(triphenylphosphine)rhodium(I) chloride in our lab for catalytic reactions. Its effectiveness in hydrogenation and Suzuki coupling was impressive, enhancing reaction yields significantly. A truly reliable catalyst for advanced research projects.