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673293

Sigma-Aldrich

Pentamethylcyclopentadienylbis(triphenylphosphine)ruthenium(II) chloride

Synonym(s):

Cp*RuCl(PPh3)2, Chloro(pentamethylcyclopentadienyl)bis(triphenylphosphine)ruthenium(II)

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About This Item

Linear Formula:
[(C10H15)Ru(P((C6H5)3))2Cl]
CAS Number:
92361-49-4
Molecular Weight:
796.32
MDL number:
MFCD09038426
UNSPSC Code:
12161600
PubChem Substance ID:
24885155
NACRES:
NA.22

form

solid

Quality Level

100

reaction suitability

core: ruthenium
reagent type: catalyst
reaction type: click chemistry

mp

128 °C (D)

storage temp.

2-8°C

SMILES string

Cl[Ru].C[C]1[C](C)[C](C)[C](C)[C]1C.c2ccc(cc2)P(c3ccccc3)c4ccccc4.c5ccc(cc5)P(c6ccccc6)c7ccccc7

InChI

1S/2C18H15P.C10H15.ClH.Ru/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-6-7(2)9(4)10(5)8(6)3;;/h2*1-15H;1-5H3;1H;/q;;;;+1/p-1

InChI key

KLXKSZDVKAWYRT-UHFFFAOYSA-M

Related Categories

Application

Catalyst employed in the cycloaddtion of azides with acetylenes giving exclusively the 1,5-disubstitutedtriazoles in contrast to the 1,4-regiochemistry commonly observed with copper catalysis. Ruthenium catalysis also enables the use of internal acetylenes in these "click cycloaddtions".
Versatile catalyst for living radical polymerization

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Li Zhang et al.
Journal of the American Chemical Society, 127(46), 15998-15999 (2005-11-17)
Cp*RuCl(PPh3)2 is an effective catalyst for the regioselective "fusion" of organic azides and terminal alkynes, producing 1,5-disubstituted 1,2,3-triazoles. Internal alkynes also participate in this catalysis, resulting in fully substituted 1,2,3-triazoles.
Metal-catalyzed living radical polymerization.
M Kamigaito et al.
Chemical reviews, 101(12), 3689-3746 (2001-12-13)

Articles

Introduction to Click Chemistry

Click chemistry is an approach to the synthesis of drug-like molecules that can accelerate the drug discovery process by using a few practical and reliable reactions.

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