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919764

Sigma-Aldrich

Grubbs Catalyst® M204 ChemBeads

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
UNSPSC Code:
12352103

form

solid

Quality Level

100

composition

~ 4 wt.% loading of catalyst

reaction suitability

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

storage temp.

2-8°C

SMILES string

CC1=CC(C)=CC(C)=C1N(CCN2C3=C(C=C(C=C3C)C)C)[C-2]2=[Ru+6](P(C4CCCCC4)(C5CCCCC5)C6CCCCC6)([Cl-])([Cl-])=[C-2]C7=CC=CC=C7

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

Related Categories

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.

ChemBeads are chemical coated glass beads. ChemBeads offer improved flowability and chemical uniformity perfect for automated solid dispensing and high-throughput experimentation. The method of creating ChemBeads uses no other chemicals or surfactants allowing the user to accurately dispense sub-milligram amounts of chemical.
Learn more about ChemBeads products

For larger scale uses, product is also available in powdered form (569747)

Other Notes

569755 Hoveyda-Grubbs Catalyst 2nd Generation

Grubbs Catalyst Technology for Olefin Metathesis by Aldrich

High-Throughput Reaction Screening with Nanomoles of Solid Reagents Coated on Glass Beads

Versatile Methods to Dispense Sub-Milligram Quantities of Solids using Chemical Coated Beads for High-Throughput Experimentation

ChemBead Enabled High-Throughput Cross-Electrophile Coupling Reveals a New Complementary Ligand

Legal Information

Grubbs Catalyst is a registered trademark of Umicore AG & Co. KG

pictograms

FlameHealth hazard
GHS02,GHS08

signalword

Danger

Hazard Classifications

Carc. 1B Inhalation - Flam. Sol. 2

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Unusual influence of substituents on ring-opening metathesis reactions
Wright D L, et al.
Organic Letters, 3(26), 4275-4277 (2002)
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)
Reversible inhibition/activation of olefin metathesis: a kinetic investigation of ROMP and RCM reactions with Grubbs' catalyst
P'Poo SJ and Schanz H-J
Journal of the American Chemical Society, 129(46), 14200-14212 (2007)
Synthesis of coumarins by ring-closing metathesis using Grubbs' catalyst
Van Tuyen N, et al.
Tetrahedron Letters, 44(22), 4199-4201 (2003)
Ana L Aguirre et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 27(51), 12981-12986 (2021-07-08)
High-throughput experimentation (HTE) methods are central to modern medicinal chemistry. While many HTE approaches to C-N and Csp2 -Csp2 bonds are available, options for Csp2 -Csp3 bonds are limited. We report here how the adaptation of nickel-catalyzed cross-electrophile coupling of

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