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729353

Sigma-Aldrich

Grubbs Catalyst® M206

Umicore

Synonym(s):

Grubbs Catalyst® M2a SIPR (C933), Dichloro[1,3-bis(2,6-isopropylphenyl)-2-imidazolidinylidene](benzylidene)(tricyclohexylphosphine)ruthenium(II)

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About This Item

Empirical Formula (Hill Notation):
C52H77Cl2N2PRu
CAS Number:
Molecular Weight:
933.13
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

form

solid

mp

176-181 °C

storage temp.

2-8°C

SMILES string

C1CCC(CC1)P(C2CCCCC2)C3CCCCC3.CC(C)c4cccc(C(C)C)c4N5CCN(C5[Ru](Cl)(Cl)=Cc6ccccc6)c7c(cccc7C(C)C)C(C)C

InChI

1S/C27H39N2.C18H33P.C7H6.2ClH.Ru/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;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;;;/h9-14,17-21H,15-16H2,1-8H3;16-18H,1-15H2;1-6H;2*1H;/q;;;;;+2/p-2

InChI key

VWYWCKUDPDENIJ-UHFFFAOYSA-L

Application

  • Bulky NHC ligand results in faster initiation than the Grubbs 2nd Generation Catalyst.
  • Has enabled lower catalyst loadings in some applications.
Grubbs Catalyst® M2a SIPr is a second generation Grubb′s catalyst used to catalyze olefin metathesis which low catalyst loading. This is also used in synthesizing variety of highly active second generation fast-initiation Hoveyda type ruthenium 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

Precautionary 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


Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

729353-VAR:
729353-500MG:
729353-2G:
729353-BULK:
729353-100MG:


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Standard System of Characterization for Olefin Metathesis Catalysts
Ritter T. et al.
Organometallics, 25 (24), 5740-5745 (2006)
Towards Long-Living Metathesis Catalysts by Tuning the N-Heterocyclic Carbene (NHC) Ligand on Trifluoroacetamide-Activated Boomerang Ru Complexes
Clavier H et al.
European Journal of Organic Chemistry, 2009 (25), 4254-4265 (2009)
Fast-Initiating, Ruthenium-based Catalysts for Improved Activity in Highly E-Selective Cross Metathesis
Ahmed, Tonia S. and Grubbs, Robert H.
Journal of the American Chemical Society, 139 (4), 1532-1537 (2017)
High Turnover Numbers with Ruthenium-Based Metathesis Catalysts
Dinger, MB and Mol JC
Advanced Synthesis & Catalysis, 344 (6-7), 671-677 (2002)
Ruthenium-Olefin Complexes: Effect of Ligand Variation upon Geometry
Anderson DR, O'Leary DJ and Grubbs RH
Chemistry?A European Journal , 14 (25), 7536-7544 (2008)

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