Grubbs catalyst 2nd generation

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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

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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)

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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

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 919764
Product name: Grubbs Catalyst® M204 ChemBeads
Packaging: 250MG
Price: $124
Updated: 2024/03/01

Sigma-Aldrich

Product number: 919764
Product name: Grubbs Catalyst® M204 ChemBeads
Packaging: 1G
Price: $311
Updated: 2024/03/01

Sigma-Aldrich

Product number: 569747
Product name: Grubbs Catalyst, 2nd Generation
Packaging: 2g
Price: $599
Updated: 2024/03/01

Sigma-Aldrich

Product number: 569747
Product name: Grubbs Catalyst, 2nd Generation
Packaging: 10g
Price: $2600
Updated: 2024/03/01

Sigma-Aldrich

Product number: 569747
Product name: Grubbs Catalyst, 2nd Generation
Packaging: 100mg
Price: $49.4
Updated: 2024/03/01

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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

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View Lastest Price from Grubbs catalyst 2nd generation manufacturers

Wuhan Circle Star Chem-medical Technology Co.,Ltd

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

Shanghai UCHEM Inc.

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

Henan Fengda Chemical Co., Ltd

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

246047-72-3, Grubbs catalyst 2nd generationRelated Search:

1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE Hoveyda-Grubbs Catalyst 2nd Generation Dichloro(p-cymene)ruthenium(II) dimer Rhodium(II) acetate dimer Ruthenium(II) chloride mesitylene dimer Tris(triphenylphosphine)rhodiu Rhodium(III) 2,4-pentanedionate Bis(tricyclohexylphosphine)nickel(II) chloride, 99% Ruthenium(III) chloride hydrate (1,5-CYCLOOCTADIENE)(PYRIDINE)(TRICYCLOHEXYLPHOSPHINE)IRIDIUM(I) HEXAFLUOROPHOSPHATE DICHLORO-[1,3-BIS(DIISOPROPYLPHENYL)IMIDAZOLYLIDENE]-(3-CHLOROPYRIDYL)PALLADIUM(II) Dichloro[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene](benzylidene)bis(3-bromopyridine)ruthenium(II) DICHLORO(O-ISOPROPOXYPHENYLMETHYLENE)(TRICYCLOHEXYLPHOSPHINE)RUTHENIUM(II) Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium Ruthenium Tricyclohexyl phosphine GRUBBS CATALYST 2ND GENERATION Tricyclohexylphosphine[3-phenyl-1H-inden-1-ylidene][1,3-bis(2,4,6-triMethylphenyl)-4,5-dihydroiMidazol-2-ylidene]rutheniuM(II)

1,3-Bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)(dichlorophenylmethylene)(tricyclohexylphosphine)ruthenium, Benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(tricyclohexylphosphine)ruthenium, (1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium

(1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-2-IMIDAZOLIDINYLIDENE)DICHLORO(PHENYLMETHYLENE)(TRICYCLOHEXYLPHOSPHINE)RUTHENIUM

RUTHENIUM,[1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-2-IMIDAZOLIDINYLIDENE]DICHLORO (PHENYLMETHYLENE) (TRICYCLOHEXYLPHOSPHINE)

Grubbs Catalyst, 2nd

RutheniuM,[1,3-bis(2,4,6-triMethylphenyl)-2-iMidazolidinylidene]dichloro(phenylMethylene)(tricyclohexylphosphine)-,(SP-5-41)-

Grubbs Gen 2nd

Catalyst, 2nd Generation

Tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]rut

Tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidine]Ruthenium(IV)dichloride

BENZYLIDENE[1,3-DIMESITYL-2-IMIDAZOL.]-C L2-(TRI-CHEX-P)-RU

Tricyclohexylphosphine1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-yli

GRUBBS CATALYST,2 ND GEN

Benzylidene(dichloro)(1,3-diMesityl-2-iMidazolidinylidene)rutheniuM - tricyclohexylphosphine (1:1)

(1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium

(SP-5-41)-[1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium

benzylidene-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichlororuthenium,tricyclohexylphosphane

Grubbs catalyst II

Grubbs Catalyst, 2nd Generation≥ 98% (NMR)

(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 [1

Grubb's second generation catalyst,97%

Grubbs Catalyst 2nd Generation,97+%

Benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene] dichloro(tricyclohexyl-phosphine) ruthenium

(1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium ,97%

(1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium ,95%

Grubbs Catalyst, 2nd Generation,(1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium, 1,3-Bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene

GRUBBS II

Grubbs2ndgenerationcatalyst

(1,3-DiMesityliMidazolin-2-ylidene)(tricyclohexylphosphine)rutheniuM dichloride

[1,3-bis(2,4,6-triMethylphenyl)iMidazolidin-2-ylidene](phenylMethylidene)(tricyclohexyl-$l^{5}-phosphanyl)rutheniuMbis(yliuM) dichloride

Grubbs Catalyst 2nd Generation Grubbs

2nd generation Grubbs catalyst

Grubb's II Catalyst

Grubbs (2nd generation)

Grubbs Catalyst, 2<SUP>nd</SUP> Generation

Grubb's second generation catalyst

GRUBBS CATALYST 2ND GENERATION

Grubbs Catalyst(TM) 2nd Generation

Grubbs 2nd

1,3-Bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)(dichlorophenyl -methylene)(tricyclohexylphosphine)ruthenium (II)

Tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-di...

Oxychlorination of Ethylene with Copper Chloride Catalyst*

(1,3-Dimesitylimidazolin-2-ylidene)

Grubbs G2

[1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-dichloro(benzylidene)(tricyclohexylphosphine)ruthenium(II)

Grubbs Catalyst??M204

[1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-dic

Grubb's Catalyst 2nd Generation

Grubbs' Catalyst 2nd Generation

Validamine Impurity 3

246047-72-3

C46H65Cl2N2PRu

Catalysis and Inorganic Chemistry

Metathesis Catalysts