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

CAS: 246047-72-3 Cat. No.: G293909 Molecular Weight: 848.97 EC Number: 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

Overview

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

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]-

Specifications & Purity

≥99.95% metals basis

Storage

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

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99.95% metals basis

Names and Identifiers

• Canonical 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
• 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
• Isomeric 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 Germany: 3
• UN Number: 1325
• Molecular Weight: 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
    • Class Azolidines
      • Subclass Imidazolidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: 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
• Description: 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

Chemical and Physical Properties

• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly, Heated
• Sensitivity: air&light sensitive
• Melt Point(°C): 143.5-148.5°C
• Molecular Weight: 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

References

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2. Xiaoxue Lin, Jianjun Shi, Zaifeng Shi, Satomi Niwayama.  (2022)  Hydrophobic and antifouling modification of graphene oxide with functionalized polynorbornene by surface-initiated ring-opening metathesis polymerization.  NEW JOURNAL OF CHEMISTRY,  46  (12): (5806-5818).  [PMID:] [10.1039/D1NJ05935A]

3. Tingting Zhang, Jin He, Ning Xu, Wang Yin, Dongli Liu, Chang Liu, Meidong Lang.  (2025)  Glass fiber-reinforced modified PDCPD composites with improving mode I and mode II interlaminar fracture toughness and impact resistance: Effects of matrix properties.  COMPOSITES PART B-ENGINEERING,      [PMID:] [10.1016/j.compositesb.2025.112225]

4. Guangzeng Luo, Feng Xu, Kai Gong, Zhilu Gao, Qianqian Hou, Yintan Huang, Shuangshuang Hu, Chuanyong Zong, Lan Lei, Hui Li.  (2024)  Pressure-Responsive Self-Lubricating Ice-Phobic Organogel with High Mechanical Strength from Fluorinated Polynorbornene Networks.  ACS Applied Polymer Materials,      [PMID:] [10.1021/acsapm.4c01190]

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6. Zhe Wang, Wen-Cong Xu, Dachuan Zhang, Man Gao, Tao Chen, Youyi Sun, Shuofeng Liang, Si Wu.  (2025)  Molecular weight regulates reversible adhesion of azopolymers with photoswitchable glass transition temperatures.  Polymer Chemistry,      [PMID:] [10.1039/D5PY00606F]

7. Tingting Zhang, Ning Xu, Wang Yin, Dongli Liu, Chang Liu, Meidong Lang.  (2024)  Energy-efficient frontal polymerization of poly(DCPD-co-TCPD) with improving thermomechanical properties and chemical resistance.  Materials Today Communications,      [PMID:] [10.1016/j.mtcomm.2024.109494]

8. Guangzeng Luo, Zhilu Gao, Cuiping Zhou, Yintan Huang, Shuangshuang Hu, Yifan Hu, Chuanyong Zong, Lan Lei, Hui Li.  (2024)  Well-Tailored Norbornene-Based Fluorinated Copolymers toward Modulating Icephobicity and Mechanical Robustness.  LANGMUIR,      [PMID:38781461] [10.1021/acs.langmuir.4c01329]

9. Peipei Ji, Xiuwu Wang, Lianpei Zhou, Guiyang Zhou, Tao Chen.  (2025)  Compartmentalization of Brönsted Acid/Pybox-Ru(II) by Polymeric Micelles for One-Pot Tandem Catalysis.  ChemistrySelect,  10  (15): (e202501120).  [PMID:] [10.1002/slct.202501120]

10. Changhai Zhang, Zhiqi Zhou, Xue Zhang, Xu Tong, Chao Wang, Tiandong Zhang, Wenju Wu, Qingguo Chi.  (2025)  Synergistic enhancement of high-temperature dielectric energy storage in polyisopren-imide based polymers via fluorination and dual physical-chemical crosslinking.  Journal of Energy Storage,      [PMID:] [10.1016/j.est.2025.118941]

11. Nan Xiao, Qi Jiao, Jieqing Shen, Hengti Wang, Xin Yang, Lian Wang, Yongjin Li.  (2026)  Arraying calcium carbonate core-shell nanoparticles densely on carbon fibers by coordination effect for interfacial enhancement of polydicyclopentadiene/carbon fiber felt (PDCPD/CFF) composites.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2026.174578]