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Merck
CN

205036

Tris(triphenylphosphine)rhodium(I) chloride

99.9% trace metals basis

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
UNSPSC Code:
12161600
NACRES:
NA.22
PubChem Substance ID:
24852305
EC Number:
238-744-5
Beilstein/REAXYS Number:
4581440
MDL number:
MFCD00010016

Key Documents

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Product Name

Tris(triphenylphosphine)rhodium(I) chloride, 99.9% trace metals basis

InChI key

IXAYKDDZKIZSPV-UHFFFAOYSA-M

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

SMILES string

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

assay

99.9% trace metals basis

reaction suitability

core: rhodium
reagent type: catalyst

Quality Level

100

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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
Useful catalyst for the efficient cross-coupling of activated alkenyl tosylates with arylboronic acids. Also used to catalyze the cleavage of allyl phenolic ethers to phenols with DABCO.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317,H413

Hazard Classifications

Aquatic Chronic 4 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW7688
MKCR6299
MKCM3707
MKBV8261V
MKBG0912V

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Sonsoles Rodriguez Aristegui et al.
Organic letters, 8(26), 5927-5929 (2006-12-15)
[Structure: see text] 2-morpholin-4-yl-4-oxo-4H-chromen-8-yl 2,2,2-trifluoromethanesulfonate is a key intermediate for the synthesis of the DNA-dependent protein kinase (DNA-PK) inhibitor 8-dibenzothiophen-4-yl-2-morpholin-4-yl-chromen-4-one (NU7441). Two improved methods for the synthesis of this triflate have been developed: (A) in 35% overall yield, through modification
European Journal of Organic Chemistry, 5260-5260 (2006)
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.
Johannes Kiefer et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 9(15), 2207-2213 (2008-09-16)
Homogeneous catalysis in room-temperature ionic liquids (ILs) constitutes a most interesting field of research with high potential in technical applications. As concerns the hydrogenation of unsaturated hydrocarbons, Wilkinson's compound RhCl(PPh(3))(3) represents a catalyst that provides high selectivity and activity. Herein
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Articles

Rhodium Catalyzed Asymmetric Suzuki Related Cross Coupling Reactions

Discover the role of boronic acids in enantioenriched C(sp2)–C(sp2) product synthesis, specifically the rhodium-catalyzed Suzuki–Miyaura-type arylations of allylic halides and cyclobutenes.

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