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
- Molecular Weight:
- 848.98
- MDL Number:
- MFCD03453237
- MOL File:
- 246047-72-3.mol
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 |
FDA UNII | 6DHB6F3EXA |
EPA Substance Registry System | Ruthenium, [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)(tricyclohexylphosphine)-, (SP-5-41)- (246047-72-3) |
SAFETY
Risk and Safety Statements
Symbol(GHS) | GHS02 |
---|---|
Signal word | Warning |
Hazard statements | H228 |
Precautionary statements | P210-P240-P241-P280-P370+P378 |
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 |
Grubbs catalyst 2nd generation price More Price(32)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich | 919764 | Grubbs Catalyst® M204 ChemBeads | 246047-72-3 | 250MG | $124 | 2024-03-01 | Buy |
Sigma-Aldrich | 919764 | Grubbs Catalyst® M204 ChemBeads | 246047-72-3 | 1G | $311 | 2024-03-01 | Buy |
Sigma-Aldrich | 569747 | Grubbs Catalyst, 2nd Generation | 246047-72-3 | 2g | $599 | 2024-03-01 | Buy |
Sigma-Aldrich | 569747 | Grubbs Catalyst, 2nd Generation | 246047-72-3 | 10g | $2600 | 2024-03-01 | Buy |
Sigma-Aldrich | 569747 | Grubbs Catalyst, 2nd Generation | 246047-72-3 | 100mg | $49.4 | 2024-03-01 | Buy |
Grubbs catalyst 2nd generation Chemical Properties,Uses,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
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.
Uses
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].
Grubbs catalyst 2nd generation Preparation Products And Raw materials
Supplier | Tel | Country | ProdList | Advantage | |
---|---|---|---|---|---|
Win-Win chemical CO., Limited | +86-0086-577-64498589 +86-15355981851 | sales@win-winchemical.com | China | 14350 | 58 |
PT CHEM GROUP LIMITED | peter68@ptchemgroup.com | China | 35426 | 58 | |
Unibest Industrial Co.,Ltd. | +86-8657427855777 +86-18758850676 | info@unibestcn.com | China | 227 | 58 |
Shanghai UCHEM Inc. | +862156762820 +86-13564624040 | sales@myuchem.com | China | 7193 | 58 |
Henan Fengda Chemical Co., Ltd | +86-371-86557731 +86-13613820652 | info@fdachem.com | China | 20293 | 58 |
Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | sales@capotchem.com | China | 29798 | 60 |
Shanghai Daken Advanced Materials Co.,Ltd | +86-371-66670886 | info@dakenam.com | China | 18628 | 58 |
Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21667 | 55 |
Shanghai Time Chemicals CO., Ltd. | +86-021-57951555 +8617317452075 | jack.li@time-chemicals.com | China | 1807 | 55 |
Hangzhou FandaChem Co.,Ltd. | 008657128800458; +8615858145714 | fandachem@gmail.com | China | 9357 | 55 |
View Lastest Price from Grubbs catalyst 2nd generation manufacturers
Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
---|---|---|---|---|---|---|---|---|
2024-09-20 | Grubbs Catalyst 2nd Generation
246047-72-3
|
US $0.00 / KG | 1KG | ≥99% | 100mt/year | Jinan Finer Chemical Co., Ltd | ||
2024-09-12 | Grubbs catalyst 2nd generation
246047-72-3
|
US $132.00-459.00 / g | 5g | 0.98 | 10kg | Shanghai UCHEM Inc. | ||
2024-04-28 | GRUBBS CATALYST 2ND GENERATION
246047-72-3
|
US $10.00-2.00 / KG | 1KG | 99% | g-kg-tons, free sample is available | Henan Fengda Chemical Co., Ltd |
- Grubbs Catalyst 2nd Generation
246047-72-3
- US $0.00 / KG
- ≥99%
- Jinan Finer Chemical Co., Ltd
- Grubbs catalyst 2nd generation
246047-72-3
- US $132.00-459.00 / g
- 0.98
- Shanghai UCHEM Inc.
- GRUBBS CATALYST 2ND GENERATION
246047-72-3
- US $10.00-2.00 / KG
- 99%
- Henan Fengda Chemical Co., Ltd
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