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667234

Sigma-Aldrich

Chloro(pentamethylcyclopentadienyl)(cyclooctadiene)ruthenium(II)

Synonym(s):

Cp*RuCl(cod), 1,5-Cyclooctadiene, ruthenium complex, Chloro(1,5-cyclooctadiene)(η5-pentamethylcyclopentadienyl)ruthenium, Chloro(1,5-cyclooctadiene)(pentamethylcyclopentadienyl)ruthenium

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About This Item

Empirical Formula (Hill Notation):
C18H27ClRu
CAS Number:
92390-26-6
Molecular Weight:
379.93
MDL number:
MFCD07369035
UNSPSC Code:
12161600
PubChem Substance ID:
24884896
NACRES:
NA.22

reaction suitability

core: ruthenium
reagent type: catalyst

mp

143-147 °C

storage temp.

−20°C

SMILES string

Cl[Ru].C1CC=CCCC=C1.C[C]2[C](C)[C](C)[C](C)[C]2C

InChI

1S/C10H15.C8H12.ClH.Ru/c1-6-7(2)9(4)10(5)8(6)3;1-2-4-6-8-7-5-3-1;;/h1-5H3;1-2,7-8H,3-6H2;1H;/q;;;+1/p-1/b;2-1-,8-7-;;

InChI key

MQMQNIQJGNBEMG-ONEVTFJLSA-M

Application

Chloro(pentamethylcyclopentadienyl)(cyclooctadiene)ruthenium(II) is a homogeneous catalyst for the formation of carbon-carbon and carbon-heteroatom bonds.
It can be used:
  • To catalyze cyclotrimerization of alkynylboronates, propargyl alcohols, and terminal alkynes to form arylboronate, which in turn undergoes palladium(II)-catalyzed carbonylation to form highly substituted phthalides.
  • To catalyze C-C coupling of norbornenes and norbornadiene with alkynes to form [2 + 2] cycloadducts.
  • In combination with 2-diphenylphosphinoethylamine-potassium tertiary butoxide to form a ternary catalyst system that can catalyze fast racemization of chiral non-racemic sec-alcohols.
  • To synthesize new organoruthenium complexes with phosphorus-based ligands such as bis(phosphino)amines.
  • To catalyze the addition of organic disulfides to alkenes leading to vic-dithioethers.

pictograms

Flame
GHS02

signalword

Danger

hcodes

H261

Hazard Classifications

Water-react 2

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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[2+ 2] Cycloaddition of norbornenes with alkynes catalyzed by ruthenium complexes
Mitsudo T-A, et al.
Angewandte Chemie (International ed. in English), 33(5), 580-581 (1994)
First Transition-Metal Complex Catalyzed Addition of Organic Disulfides to Alkenes Enables the Rapid Synthesis of v icinal-Dithioethers
Kondo T, et al.
Journal of the American Chemical Society, 121(2), 482-483 (1999)
The versatility of molecular ruthenium catalyst RuCl(COD)(C5Me5)
D'erien S and Dixneuf PH
Journal of Organometallic Chemistry, 689(8), 1382-1392 (2004)
Cp*RuCl-catalyzed formal intermolecular cyclotrimerization of three unsymmetrical alkynes through a boron temporary tether: Regioselective four-component coupling synthesis of phthalides
Yamamoto Y, et al.
Journal of the American Chemical Society, 127(26), 9625-9631 (2005)
Rapid racemization of chiral non-racemic sec-alcohols catalyzed by (η5-C5(CH3)5)Ru complexes bearing tertiary phosphine-primary amine chelate ligands
Ito M, et al.
Tetrahedron Letters, 44(40), 7521-7523 (2003)
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