569755

Sigma-Aldrich

Hoveyda-Grubbs Catalyst® M720

Umicore, 97%

Synonym(s):
Grubbs Catalyst® C627, Hoveyda-Grubbs Catalyst® 2nd Generation, (1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(o-isopropoxyphenylmethylene)ruthenium, Hoveyda-Grubbs Catalyst® M72 (C627), Dichloro[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene](2-isopropoxyphenylmethylene)ruthenium(II)
Empirical Formula (Hill Notation):
C31H38Cl2N2ORu
CAS Number:
Molecular Weight:
626.62
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

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

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), ring-closing metathesis (RCM), ring-opening metathesis (ROM), and a sequence of a metathesis reaction and subsequent dihydroxylation of the newly formed double bond.

Packaging

2, 10, 25 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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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)
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.
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...
Sequential catalysis: a metathesis/dihydroxylation sequence.
Samuel Beligny et al.
Angewandte Chemie (International ed. in English), 45(12), 1900-1903 (2006-02-14)
Vougioukalakis, G. C.; Grubbs, R. H.
Chemical Reviews, 1746-1746 (2010)

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