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Grubbs Catalyst® M204

Umicore

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Synonym(s):
(1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium, Benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(tricyclohexylphosphine)ruthenium, Dichloro[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene](benzylidene)(tricyclohexylphosphine)ruthenium(II), Grubbs Catalyst® 2nd Generation, Grubbs Catalyst® M2a (C848)
Empirical Formula (Hill Notation):
C46H65Cl2N2PRu
CAS Number:
Molecular Weight:
848.97
PubChem Substance ID:
NACRES:
NA.22

Quality Level

form

solid

reaction suitability

core: ruthenium
reagent type: catalyst
reaction type: Ring-Opening Polymerization

mp

143.5-148.5 °C

storage temp.

2-8°C

SMILES string

CC1=CC(C)=CC(C)=C1N2CCN(C3=C(C)C=C(C)C=C3C)C2=[Ru](Cl)(Cl)=CC4=CC=CC=C4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7

InChI

1S/C21H26N2.C18H33P.C7H6.2ClH.Ru/c1-14-9-16(3)20(17(4)10-14)22-7-8-23(13-22)21-18(5)11-15(2)12-19(21)6;1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-7-5-3-2-4-6-7;;;/h9-12H,7-8H2,1-6H3;16-18H,1-15H2;1-6H;2*1H;/q;;;;;+2/p-2

InChI key

FCDPQMAOJARMTG-UHFFFAOYSA-L

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This Item
682330579726682365
reaction suitability

core: ruthenium, reagent type: catalyst
reaction type: Ring-Opening Polymerization

reaction suitability

core: ruthenium, reagent type: catalyst
reaction type: Ring-Opening Polymerization

reaction suitability

core: ruthenium, reagent type: catalyst
reaction type: Ring-Opening Polymerization

reaction suitability

core: ruthenium, reagent type: catalyst
reaction type: Olefin Metathesis

mp

143.5-148.5 °C

mp

140 °C (dec.)

mp

153 °C (dec.)

mp

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

Application

Grubbs Catalyst® M204 can be used as a catalyst for ring-closing metathesis (RCM), cross-metathesis, and ring-opening metathesis polymerization (ROMP). It is also used to synthesize trisubstituted olefins with excellent functional group tolerance and selectivity via cross-metathesis and ring closing metathesis reactions.
It can also be used as a catalyst:

  • To synthesize coumarins from phenolic compounds via RCM.
  • To cleave secondary (E)-allyl vic-diols to aldehydes.
For small scale and high throughput uses, product is also available as ChemBeads (919764)

Learn more about our metathesis catalysts

Legal Information

Product of Umicore

Product License
This product, its manufacturing or use, is the subject of one or more issued or pending U.S. Patents (and foreign equivalents) owned or controlled by Umicore PMC. The purchase of this product from Umicore PMC through Sigma-Aldrich, its affiliates or their authorized distributors conveys to the buyer a limited, one-time, non-exclusive, non-transferable, non-assignable license. Buyer′s use of this product may infringe patents owned or controlled by third parties. It is the sole responsibility of buyer to ensure that its use of the product does not infringe the patent rights of third parties or exceed the scope of the license granted herein.

For any further information on product please refer to your local Umicore PMC contact at http://www.pmc.umicore.com
Grubbs Catalyst is a registered trademark of Umicore AG & Co. KG

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Hazard Classifications

Flam. Sol. 2

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis of coumarins by ring-closing metathesis using Grubbs? catalyst
Van Tuyen N, et al.
Tetrahedron Letters, 44(22), 4199-4201 (2003)
Reversible inhibition/activation of olefin metathesis: a kinetic investigation of ROMP and RCM reactions with Grubbs' catalyst
P'Poo SJ and Schanz H-J
Journal of the American Chemical Society, 129(46), 14200-14212 (2007)
A modified three-field technique for breast treatment.
Svensson GK, et al.
International Journal of Radiation Oncology, Biology, Physics, 6(6), 689-694 (1980)
D L Wright et al.
Organic letters, 3(26), 4275-4277 (2002-01-11)
The ring-opening cross-metathesis of oxabicyclo[3.2.1]octene derivatives provides a convenient method for preparing differentially substituted 4-pyrones. The major competing reaction is the ring-opening metathesis polymerization of the bridged olefin. Studies on this reaction have shown that substituents on the bicyclic alkene
Novel cleavage of (E)-allyl vic-diols to aldehydes using the 2nd-generation Grubbs catalyst
H Chunguang and U Daisuke
Tetrahedron Letters, 49(49), 6988-6990 (2008)

Protocols

TPGS-750-M, a second generation surfactant, may be used in water at room temperature for Buchwald-Hartwig Amination, Suzuki-Miyaura reactions, Heck reactions, Sonogashira reactions, Negishi reactions, and olefin metathesis.

Related Content

Research in the Grubbs group has centered on the development and application of a suite of highly active, selective, and bench stable ruthenium alkylidene complexes capable of catalyzing versatile olefin metatheses.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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