Grubbs catalyst 2nd generation
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)
- CAS NO.:246047-72-3
- Empirical Formula: C46H65Cl2N2PRu
- Molecular Weight: 848.98
- MDL number: MFCD03453237
- EINECS: 688-322-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2026-02-28 15:23:14
What is Grubbs catalyst 2nd generation?
Chemical properties
pink-brown to red-purple crystals or powder
Characteristics
Grubbs catalyst is a kind of coordination compound used in olefin metathesis reaction, and the ligand in it has a great influence on the catalytic performance and stability of the catalyst. Grubbs second-generation catalysts are more active than first-generation catalysts and have a wider substrate range, including sterically demanding or deactivated olefins such as 1,1-disubstituted olefins and α,β-non- Saturated carbonyl compounds.
The Uses of Grubbs catalyst 2nd generation
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.
The Uses of Grubbs catalyst 2nd generation
suzuki reaction
Definition
Adlhart and Chen found that ligand rotation is the difference between the activity of the first and second-generation Grubbs catalysts. This difference is brought about by a difference in the symmetry of the ligands. The phosphine ligand has a threefold symmetry, which causes a high barrier in the middle of the reaction coordinate, which is forced by the need for rotation of the phosphine. However, the barrier is absent for the second-generation Grubbs catalyst, with twofold symmetry of the NHC ligand. The rate-limiting step for second-generation catalysts is always phosphine dissociation[2].
Properties of Grubbs catalyst 2nd generation
| Melting point: | 143.5-148.5 °C(lit.) |
| storage temp. | 2-8°C |
| solubility | Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly, Heated) |
| form | Solid |
| color | Brown to Very Dark Brown to Very Dark Red |
| EPA Substance Registry System | Ruthenium, [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)(tricyclohexylphosphine)-, (SP-5-41)- (246047-72-3) |
Safety information for Grubbs catalyst 2nd generation
| Signal word | Warning |
| Pictogram(s) |
![]() Flame Flammables GHS02 |
| GHS Hazard Statements |
H228:Flammable solids |
| Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P240:Ground/bond container and receiving equipment. P241:Use explosion-proof electrical/ventilating/lighting/…/equipment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P370+P378:In case of fire: Use … for extinction. |
Computed Descriptors for Grubbs catalyst 2nd generation
| InChIKey | FCDPQMAOJARMTG-UHFFFAOYSA-L |
| SMILES | P(C1CCCCC1)(C1CCCCC1)(C1CCCCC1)[Ru+6](=[C-2]1N(C2C(=CC(C)=CC=2C)C)CCN1C1C(=CC(C)=CC=1C)C)([Cl-])([Cl-])=[C-2]C1C=CC=CC=1 |
Grubbs catalyst 2nd generation manufacturer
ALS India Life Sciences Pvt. Ltd
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