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199982

Sigma-Aldrich

Tris(triphenylphosphine)rhodium(I) chloride

Synonym(s):

NSC 124140, RhCl(PPh3)3, Rhodium(I) tris(triphenylphosphine) chloride, Wilkinson’s catalyst

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About This Item

Linear Formula:
[(C6H5)3P]3RhCl
CAS Number:
14694-95-2
Molecular Weight:
925.22
Beilstein:
4581440
EC Number:
238-744-5
MDL number:
MFCD00010016
UNSPSC Code:
12352300
PubChem Substance ID:
24851950
NACRES:
NA.22

Quality Level

200

reaction suitability

core: rhodium
reagent type: catalyst

SMILES string

Cl[Rh].c1ccc(cc1)P(c2ccccc2)c3ccccc3.c4ccc(cc4)P(c5ccccc5)c6ccccc6.c7ccc(cc7)P(c8ccccc8)c9ccccc9

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;/q;;;;+1/p-1

InChI key

IXAYKDDZKIZSPV-UHFFFAOYSA-M

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General description

Tris(triphenylphosphine)rhodium(I) chloride is used as a decarbonylation reagent and as a cocatalyst in Heck reaction.

Application

Hydrosilylation Catalysts

Catalyst used for many organic reactions including:
  • Chemoselective allylic alkylations
  • Stoichiometric activation of Si-H bonds and hydrosilylations
  • Inter- and intramolecular hydroacylation of alkenes along with a cocatalyst
  • Polymerization of diorganostannanes

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317 - H413

Hazard Classifications

Aquatic Chronic 4 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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The Journal of Organic Chemistry, 57, 5075-5075 (1992)
Chemical Reviews, 91, 1179-1179 (1991)
Effect of catalytic hydrogenation of cellular lipid and fatty acid on the susceptibility of tumor cells to humoral immune killing.
S I Schlager
Methods in enzymology, 73(Pt B), 191-199 (1981-01-01)
V P Shevchenko et al.
Bioorganicheskaia khimiia, 36(2), 283-288 (2010-06-10)
1,2-Tritium-labeled 3-(O-carboxypropyl)- and 3-(O-carbomethoxypropyl)-oximes of 6alpha-methyl-16alpha,17alpha-cyclohexanopregn-4-ene-3,20-diones were obtained by the homogeneous catalytic hydrogenation of 1,2-dehydroprecursors with gaseous tritium and the subsequent separation of the resulting mixtures by HPLC. The specific radioactivities of 50-55 Ci/mmol were prepared using tris-(triphenylphosphine)-rhodium chloride.
P Andrew Evans et al.
Journal of the American Chemical Society, 124(30), 8782-8783 (2002-07-26)
Transition metal-catalyzed cycloaddition reactions represent powerful methods for the construction of complex polycyclic systems. We have developed a new intermolecular metal-catalyzed [4 + 2 + 2] cycloaddition of heteroatom-tethered enyne derivatives with 1,3-butadiene. This study demonstrates that excellent selectivity can
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Articles

Alkyne Hydrosilylation

Vinyl-metal reagents play a pivotal role in organic synthesis. Among the vinyl-metal reagents available, silicon-based reagents are of increasing importance. This is largely due to their low cost, minimal toxicity, ease of handling, and the simplicity of byproduct removal.

Hydrosilylation Catalyst

A Highly Efficient Hydrosilylation Catalyst, sigma-aldrich is pleased to offer [Cp*Ru(MeCN)3]PF6, as well as a number of other catalysts for hydrosilylation.

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