Grubbs catalyst 2nd generation
Description Reference- Product Name
- Grubbs catalyst 2nd generation
- CAS No.
- 246047-72-3
- Chemical Name
- Grubbs catalyst 2nd generation
- Synonyms
- GRUBBS II;Grubbs 2nd;Grubbs catalyst II;Grubbs Gen 2nd;2nd generation Grubbs catalyst;(1,3-DiMesityliMidazolin-2-ylidene)(tricyclohexylphosphine)rutheniuM dichloride;Benzylidene(dichloro)(1,3-diMesityl-2-iMidazolidinylidene)rutheniuM - tricyclohexylphosphine (1:1);benzylidene-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichlororuthenium,tricyclohexylphosphane;(1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium;Grubbs G2
- CBNumber
- CB4322469
- Molecular Formula
- C46H65Cl2N2PRu
- Formula Weight
- 848.98
- MOL File
- 246047-72-3.mol
Grubbs catalyst 2nd generation Property
- 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
- 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
- EPA Substance Registry System
- Ruthenium, [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)(tricyclohexylphosphine)-, (SP-5-41)- (246047-72-3)
Safety
- Hazard Codes
- F
- Risk Statements
- 36/37/38-11
- Safety Statements
- 26-36/37/39
- RIDADR
- 1325
- WGK Germany
- 3
- F
- 10-23
- HazardClass
- 4.1
- PackingGroup
- Ⅱ
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H228Flammable solid
- Precautionary statements
-
P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P240Ground/bond container and receiving equipment.
P241Use explosion-proof electrical/ventilating/lighting/…/equipment.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P370+P378In case of fire: Use … for extinction.
N-Bromosuccinimide Price
- Product number
- 919764
- Product name
- Grubbs Catalyst® M204 ChemBeads
- Packaging
- 250MG
- Price
- $124
- Updated
- 2024/03/01
- Product number
- 919764
- Product name
- Grubbs Catalyst® M204 ChemBeads
- Packaging
- 1G
- Price
- $311
- Updated
- 2024/03/01
- Product number
- 569747
- Product name
- Grubbs Catalyst, 2nd Generation
- Packaging
- 2g
- Price
- $599
- Updated
- 2024/03/01
- Product number
- 569747
- Product name
- Grubbs Catalyst, 2nd Generation
- Packaging
- 10g
- Price
- $2600
- Updated
- 2024/03/01
- Product number
- 569747
- Product name
- Grubbs Catalyst, 2nd Generation
- Packaging
- 100mg
- Price
- $49.4
- Updated
- 2024/03/01
Grubbs catalyst 2nd generation Chemical Properties,Usage,Production
Description
Grubbs catalysts are a series of transition metal carbene complexes used as catalyst for olefin metathesis.1 The Grubbs catalysts are based on a ruthenium atom surrounded by five ligands: two neutral electron-donating entities (e.g., trialkylphosphines, N-heterocyclic carbenes), two monoanionic groups (e.g., halides), and one alkylidene moiety (e.g., unsubstituted and substituted methylidenes). L2X2Ru=CHR complexes (where L is a phosphine ligand) were discovered first and are referred to as the first-generation Grubbs catalyst. (L)(L’)X2Ru=CHR complexes (where L is a phosphine ligand and L’ a saturated N-heterocyclic carbene or NHC ligand) are referred to as the second-generation Grubbs catalysts.
The first-generation Grubbs catalysts show attractive functional-group tolerance and handling properties and have been widely used as highly efficient promoters for ring opening metathesis polymerizations, ring-closing metathesis reactions to make disubstituted olefins, ethenolysis (i.e., cleavage of the carbon–carbon double bond), cross-metathesis of terminal olefins, and the preparation of 1,3-dienes via enyne metathesis. These catalysts and analogues are still widely used in important processes, including the ethenolysis of feedstocks derived from bio-renewable seed oils and the manufacture of macrocyclic hepatitis C therapeutics. Nevertheless, the first-generation Grubbs catalysts show limitations with electron-poor and electron-rich double bonds as well as with sterically hindered systems. The second-generation Grubbs catalysts with excellent metathesis activity while retaining the handling characteristics and broad functional-group tolerance of the earlier Grubbs catalysts are thereby developed. At the same time, the second-generation catalysts are stable against moisture and air.
Reference
[1] M. L. Crawley, B. M. Trost, Applications of Transition Metal Catalysis in Drug Discovery and Development, 2012, ISBN 978-0-470-63132-4.
[2] J.I. du Toit, H.C.M. Vosloo, C.G.C.E. van Sittert. “Metal carbenes in homogeneous alkene metathesis: Computational investigations.” Journal of Organometallic Chemistry 738 (2013): Pages 76-91.
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.
Uses
suzuki reaction
Uses
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.
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].
reaction suitability
reagent type: catalyst
core: ruthenium
reaction type: Ring-Opening Polymerization
Grubbs catalyst 2nd generation Preparation Products And Raw materials
Raw materials
Preparation Products
Grubbs catalyst 2nd generation Suppliers
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View Lastest Price from Grubbs catalyst 2nd generation manufacturers
- Product
- GRUBBS CATALYST 2ND GENERATION 246047-72-3
- Price
- US $0.00-0.00/g
- Min. Order
- 1g
- Purity
- 98
- Supply Ability
- 1000
- Release date
- 2025-01-07
- Product
- Grubbs catalyst 2nd generation 246047-72-3
- Price
- US $132.00-459.00/g
- Min. Order
- 5g
- Purity
- 0.98
- Supply Ability
- 10kg
- Release date
- 2023-12-13
- Product
- GRUBBS CATALYST 2ND GENERATION 246047-72-3
- Price
- US $10.00-2.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2024-04-28