Grubbs Catalyst, 2nd Generation - ≥99.95% metals basis , CAS No.246047-72-3

CAS: 246047-72-3 Cat. No.: G293909 Summenformel: C₄₆H₆₅Cl₂N₂PRu Molekulargewicht: 848.97 EG-Nummer: 688-322-3

GRADE & PURITY ≥99.95% metals basis

Synonyms

246047-72-3|Grubbs Catalyst 2nd Generation|(1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium|Grubbs Catalyst, 2nd Generation|benzylidene-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Übersicht

Grubbs 2nd Generation Catalyst Generally more active compared to 1st generation catalysts and with a broader substrate scope, including sterically demanding or deactivated olefins such as 1,1-disubstituted olefins and α,β-unsaturated carbonyls

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.

Product class
M-P, Homogeneous Catalysts, N-Heterocyclic Carbene Ligands, M-C, Grubbs Catalyst® 2nd Generation, Carbene Ligands, SIMes, Phosphorus Ligands - Achiral

Reaction type
Alkene Metathesis, Acyclic Diene Metathesis, Cross Metathesis, Ring Arrangement Metathesis , Ring Closing Metathesis, Ring Opening Metathesis, Ring Opening Metathesis Polymerization, Self Metathesis

Chemical properties

Chemical formula

C46H65Cl2N2PRu

Empirical formula

(SIMes)Ru(PCy3)(benzylidene)Cl2

Molecular weight

848.97

Metal

Ru

Theoretical metal content

12

Physical state

powder

Color

orange-brown

Metal purity

99.95

Applications & references

Asymmetric synthesis of new cyclic fluorinated amino-acids

Reference: European Journal of Organic Chemistry, March 2018

Photoinduced strain-assisted synthesis of a stiff-stilbene polymer by ring-opening metathesis polymerization.

Reference: Chem. Eur. J. 2020 (10.1002/chem.20200418)

Facile synthetic route to [3.n]thiacyclophanes via ring-closing metathesis.

Reference: Eur. J. Org. Chem. 2020 (10.1002/ejoc.202000697)

RCM-Based Total Synthesis of the Antibiotic Disciformycin B.

Reference: Angew. Chem. Int. Ed. 2020 (doi.org/10.1002/anie.202004589)

Sequential two-fold Claisen Rearrangement, One-pot Ring Closing Metathesis and Cross-metathesis as a Route to Substituted Benzo[b]azepine-2-one, Benzo[b]azepine and Benzo[b]oxepine Derivatives.

Reference: Helv Chem Acta 2020 ASAP (doi.org/10.1002/hlca.202000216)

Sequence-regulated vinyl polymers via iterative atom transfer radical additions and acyclic diene metathesis polymerization.

Reference: Polym Chem 2020 ASAP (doi.org/10.1039/D0PY01564D)

Specifications

Synonyme

246047-72-3 | Grubbs Catalyst 2nd Generation | (1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium | Grubbs Catalyst, 2nd Generation | benzylidene-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-

Spezifikationen & Reinheit

≥99.95% metals basis

Storage

Store at 2-8°C,Protected from light,Argon charged

Verschickt in

Wet ice

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Reinheit

≥99.95% metals basis

Namen und Kennungen

Pubchem Sid

508810576

Kanonisches Lächeln

CC1=CC(=C(C(=C1)C)N2CCN(C2=[Ru](=CC3=CC=CC=C3)(Cl)Cl)C4=C(C=C(C=C4C)C)C)C.C1CCC(CC1)P(C2CCCCC2)C3CCCCC3

IUPAC Name

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

InChIKey

FCDPQMAOJARMTG-UHFFFAOYSA-L

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

Isomere SMILES

CC1=CC(=C(C(=C1)C)N2CCN(C2=[Ru](=CC3=CC=CC=C3)(Cl)Cl)C4=C(C=C(C=C4C)C)C)C.C1CCC(CC1)P(C2CCCCC2)C3CCCCC3

WGK Deutschland

3

UN-Nummer

1325

Molekulargewicht

848.97

Reaxy-Rn

14310434

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=14310434&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Klasse Azolidines
      • Subclass Imidazolidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Klasse: Azolidines
• Subclass: Imidazolidines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylimidazolidines
• Alternative Parents: Aniline and substituted anilines Organic phosphines and derivatives Organic transition metal salts Azacyclic compounds Organotransition metal compounds Hydrocarbon derivatives Amines
• Molecular Framework: Not available
• Substituents: Phenylimidazolidine - Aniline or substituted anilines - Monocyclic benzene moiety - Benzenoid - Phosphine - Azacycle - Organic metal salt - Organic transition metal salt - Organophosphorus compound - Organonitrogen compound - Organometallic compound - Organic transition metal moeity - Hydrocarbon derivative - Amine - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as phenylimidazolidines. These are polycyclic compounds containing an imidazoline substituted by a phenyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemische und physikalische Eigenschaften

• Löslichkeit: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly, Heated
• Empfindlichkeit: air&light sensitive
• Schmelzpunkt (°C): 143.5-148.5°C
• Molekulargewicht: 849.000 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 848.331 Da
• Monoisotopic Mass: 848.331 Da
• Topological Polar Surface Area: 6.500 Ų
• Heavy Atom Count: 52
• Formal Charge: 0
• Complexity: 927.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3