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Sigma-Aldrich

Hoveyda-Grubbs Catalyst® M720

Umicore, 97%

Synonym(s):

Hoveyda-Grubbs Catalyst® 2nd Generation, Hoveyda-Grubbs Catalyst® M72 (C627), (1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(o-isopropoxyphenylmethylene)ruthenium, Dichloro[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene](2-isopropoxyphenylmethylene)ruthenium(II), Grubbs Catalyst® C627

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100 MG
¥784.48

¥784.48

Available to ship on2025年4月27日Details

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100 MG
¥784.48

About This Item

Empirical Formula (Hill Notation):
C31H38Cl2N2ORu
CAS Number:
301224-40-8
Molecular Weight:
626.62
MDL number:
MFCD03701614
UNSPSC Code:
12161600
PubChem Substance ID:
24880520
NACRES:
NA.22

¥784.48

Available to ship on2025年4月27日Details

Request a Bulk Order

Quality Level

100

Assay

97%

form

solid

reaction suitability

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

mp

216-220 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C

InChI

1S/C21H26N2.C10H12O.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;1-8(2)11-10-7-5-4-6-9(10)3;;;/h9-12H,7-8H2,1-6H3;3-8H,1-2H3;2*1H;/q;;;;+2/p-2

InChI key

ZRPFJAPZDXQHSM-UHFFFAOYSA-L

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Application

It′s a phosphine free version of Grubbs 2nd Generation Catalyst with comparable reactivity, but initiates more readily at lower temperatures. Efficient for metathesis of electron-deficient substrates including fluorinated olefins. Demonstrated in multiple large-scale pharmaceutical applications.
It can be used as a catalyst for olefin cross-metathesis with fluorinated olefins (CM),[1] ring-closing metathesis (RCM),[2] ring-opening metathesis (ROM),[3] and a sequence of a metathesis reaction and subsequent dihydroxylation of the newly formed double bond.[4]

Learn more about our metathesis catalysts

Other Notes

Grubbs Catalyst® Technology for Olefin Metathesis by Aldrich

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

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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

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
    MKCX7110
    MKCX3517
    MKCV8404
    MKCW6535
    MKCT8210

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    Synthesis of the HCV protease inhibitor Vaniprevir (MK-7009) using ring-closing metathesis strategy.
    Kong J, et al.
    The Journal of Organic Chemistry, 77(8), 3820-3828 (2012)
    Structure activity relationships of 5-, 6-, and 7-methyl-substituted azepan-3-one cathepsin K inhibitors.
    Yamashita DS, et al.
    Journal of Medicinal Chemistry, 49(5), 1597-1612 (2006)
    Kevin M Kuhn et al.
    Organic letters, 12(5), 984-987 (2010-02-10)
    A series of ruthenium catalysts have been screened under ring-closing metathesis (RCM) conditions to produce five-, six-, and seven-membered carbamate-protected cyclic amines. Many of these catalysts demonstrated excellent RCM activity and yields with as low as 500 ppm catalyst loadings.
    Brian H White et al.
    Journal of the American Chemical Society, 125(48), 14901-14904 (2003-12-04)
    Ring-opening/ring-closing metathesis on cyclobutene-containing substrates with angular oxygen functionality provides a stereospecific introduction of 1,5-bis-dienes required for an anion-accelerated oxy-Cope rearrangement. The reaction sequence offers generally a stereocontrolled preparation of a variety of medium ring-containing bicyclic ring systems, while rearrangement
    S Imhof et al.
    Chemical communications (Cambridge, England), (17), 1692-1693 (2002-09-21)
    The E-selective cross metathesis (CM) of fluorinated olefins with various functionalised alkenes in good to excellent yields is reported.
    View All Related Papers

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    Grubbs Group – Prof. Product Portal

    Research focuses on ruthenium alkylidene complexes for versatile olefin metatheses catalysis in the Grubbs group.

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