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569747

Sigma-Aldrich

Grubbs Catalyst® M204

Grubbs Catalyst® M204

Umicore

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)

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About This Item

Empirical Formula (Hill Notation):
C46H65Cl2N2PRu
CAS Number:
246047-72-3
Molecular Weight:
848.97
MDL number:
MFCD03453237
UNSPSC Code:
12352302
PubChem Substance ID:
329758255
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

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

Application

Grubbs Catalyst® M204 can be used as a catalyst for ring-closing metathesis (RCM), cross-metathesis, and ring-opening metathesis polymerization (ROMP).[1][2][3] It is also used to synthesize trisubstituted olefins with excellent functional group tolerance and selectivity via cross-metathesis and ring closing metathesis reactions.[4][5]
It can also be used as a catalyst:

  • To synthesize coumarins from phenolic compounds via RCM.[1]
  • To cleave secondary (E)-allyl vic-diols to aldehydes.[6]
For small scale and high throughput uses, product is also available as ChemBeads (919764)

Learn more about our metathesis catalysts

Other Notes

Grubbs Catalyst® Technology for Olefin Metathesis by Aldrich
569755 Hoveyda-Grubbs Catalyst® 2nd Generation

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
GHS02

Signal Word

Warning

Hazard Statements

H228

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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Certificates of Analysis (COA)

Lot/Batch Number
0000413686
0000413686
0000413687
0000413687
0000408721

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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 coumarins by ring-closing metathesis using Grubbs? catalyst
Van Tuyen N, et al.
Tetrahedron Letters, 44(22), 4199-4201 (2003)
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
A modified three-field technique for breast treatment.
Svensson GK, et al.
International Journal of Radiation Oncology, Biology, Physics, 6(6), 689-694 (1980)
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)
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Questions

1–8 of 8 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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

    1 answer

    1. Commercial quantities are available directly from Materia.  Their phone number is 626-584-8400, or their e-mail address is [email protected].

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

    1 answer

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

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

    1 answer

    1. 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.

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

    1 answer

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

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

    1 answer

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

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

    1 answer

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

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