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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:
12161600
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)
Stereochemistry of tris (triphenylphosphine) rhodium chloride decarbonylation of aldehydes
HM Walborsky et al.
Journal of the American Chemical Society, 93, 5465-5468 (1971)
Palladium (II) acetate- Tris (triphenylphosphine) rhodium (I) chloride: a novel catalytic couple for the intramolecular heck reaction
Donald B
The Journal of Organic Chemistry, 64, 3461-3466 (1999)
Chemical Reviews, 91, 1179-1179 (1991)
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.
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Trost group's protocol yields α-vinylsilanes from terminal acetylenes using [Cp*Ru(MeCN)3]PF6 catalyst and others for hydrosilylation.

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