569747

Sigma-Aldrich

Grubbs Catalyst® M204

Umicore

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

Quality Level

reaction suitability

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

mp

143.5-148.5 °C

storage temp.

2-8°C

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.

Packaging

2, 10 g in glass bottle
100, 500 mg in glass bottle

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

pictograms

Flame

signalword

Warning

hcodes

hazcat

Flam. Sol. 2

storage_class_code

4.1B - Flammable solid hazardous materials

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What benefits does Product 569747, Grubbs Catalyst, 2nd Generation, have over other olefin metathesis catalysts?

    Grubbs' Catalysts are extraordinarily versatile.  They tolerate other functional groups in the alkene and are compatible with a wide range of solvents.

  4. What types of reactions is Product 569747, Grubbs Catalyst, 2nd Generation, used in?

    It is often used in organic synthesis to achieve olefin cross-metathesis, ring-opening metathesis polymerization (ROMP), and ring-closing metathesis.

  5. What is the difference between the First and Second Generation Grubbs Catalyst?

    The Second Generation Catalyst has the same uses in organic synthesis as the First Generation Catalyst, but it has a higher activity.

  6. How do I order larger quantities of Product 569747, Grubbs Catalyst, 2nd Generation?

    Commercial quantities are available directly from Materia.  Their phone number is 626-584-8400, or their e-mail address is info@materia-inc.com.

  7. Is it necessary to handle Product 569747, Grubbs Catalyst, 2nd Generation, under inert atmosphere?

    The Grubbs Catalyst is air sensitive.  Therefore, we do recommend to handle and store under nitrogen atmosphere.

  8. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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...
Highly selective cross-metathesis with phenyl vinyl sulphone using the `second generation?Grubbs? catalyst
Grela K and Bieniek M
Tetrahedron Letters, 42(36), 6425-6428 (2001)
Synthesis of symmetrical trisubstituted olefins by cross metathesis
Chatterjee AK, et al.
Organic Letters, 4(11), 1939-1942 (2002)
Total synthesis of amphidinolide Y by formation of trisubstituted (E)-double bond via ring-closing metathesis of densely functionalized alkenes
Jin Jian, et al.
Organic Letters, 9(13), 2585-2588 (2007)
Synthesis of coumarins by ring-closing metathesis using Grubbs? catalyst
Van Tuyen N, et al.
Tetrahedron Letters, 44(22), 4199-4201 (2003)
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