Grubbs second generation catalyst

Manufactured by Merck Group

Sourced in Australia, United States

Grubbs second-generation catalyst is a ruthenium-based olefin metathesis catalyst. It is a homogeneous catalyst used in organic chemistry for the formation and rearrangement of carbon-carbon double bonds.

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Lab products found in correlation

8 protocols using grubbs second generation catalyst

Peptide Synthesis and Modification Protocols

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Fmoc-Aib-OH, Boc-Aib-OH, Boc-Ser-OH, Fmoc-OSu,
2-chlorotrityl chloride polystyrene resin, 1-hydroxy-7-azabenzotrizole
(HOAt) and 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl
uronium hexafluorophosphate methanaminium (HATU) were purchased from
GL Biochem (Shanghai) Ltd., China. Dichloromethane (DCM), diethyl
ether (Et₂O), ethyl acetate (EtOAc), methanol and ethanol
were purchased from Ajax Finechem Pty Ltd. (Australia). Piperidine,
acetonitrile, propan-2-ol and N,N-dimethylformamide (DMF) were purchased from Merck, Australia. Anhydrous N,N-dimethylformamide (DMF), dimethyl sulfoxide
(DMSO), tetrahydrafuran (THF), Second-generation Grubbs’ catalyst,
Pd/C catalyst, ethyl vinyl ether, 2,2,2-trifluoroethanol (TFE), trifluoroacetic
acid (TFA), 4 M HCl/dioxane solution, N,N′-dicyclohexylcarbodiimide (DCC), dimethylaminopyridine (DMAP),
cysteamine and diisopropylethylamine (DIPEA) were purchased from Sigma-Aldrich,
Australia. NaOH was purchased from Chem Supply, Australia. Single-walled
carbon nanotubes (P2-SWCNTs) were purchased from Carbon Solutions,
Inc., USA. Boc-Ser(Al)-OH^{24 (link)} and ferrocenylmethylamine^{25 ,26} were prepared as published. All solvents and reagents were used
without purification unless noted.

Horsley J.R., Yu J., Moore K.E., Shapter J.G, & Abell A.D. (2014). Unraveling the Interplay of Backbone Rigidity and Electron Rich Side-Chains on Electron Transfer in Peptides: The Realization of Tunable Molecular Wires. Journal of the American Chemical Society, 136(35), 12479-12488.

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Facile Synthesis of Polymer Composites

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Dicyclopentadiene (DCPD), 5-ethylidene-2-norbonene (ENB), second-generation Grubbs’ catalyst (GC2), phenylcyclohexane (PCH), allyl chloride, urea, sodium hydroxide (NaOH), hydrochloric acid (HCl), and decylamine were purchased from Sigma-Aldrich and used as received. Tannic acid was obtained from Alfa Aesar and used without modification. Tributyl phosphite inhibitor (TBP) was purchased from TCI-Sejin CI. Acetone (99.5%) was purchased from Dae Jung Chemical and used without further purification. Cellulose nanocrystal (CNC) was acquired from Nanografi Nano Technology and used as received. A 26V-65W FX-8801 HAKO soldering iron was used to trigger FP. ISTEK Multimeter CP-500L was used to adjust pH levels. 15 × 150 mm glass test tubes (Tube 2, 15150) were purchased from Dai Han Scientific. 1.5 × 80 mm Borokapillaren capillary tubes were purchased from Muller GmbH. T-type welded thermocouples were purchased from Omega Engineering. TM947SD digital thermometer from Lutron Instruments was used to record temperature values during the FP reaction.

Park J, & Kwak S.Y. (2022). Frontal polymerization-triggered simultaneous ring-opening metathesis polymerization and cross metathesis affords anisotropic macroporous dicyclopentadiene cellulose nanocrystal foam. Communications Chemistry, 5, 119.

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Synthesis and Characterization of Oxonorbornene Monomers

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Reagent-grade maleic acid anhydride, furan, 1-butanol, 4-(dimethylamino)pyridine, dicyclohexyl carbodiimide, and N-Boc-ethanolamine, which were used for oxonorbornene monomer synthesis, were purchased from Sigma-Aldrich and used as received. Solvents needed for the synthesis including toluene (dry), tetrahydrofurane (dry), dichloromethane (freshly distilled from CaH₂), and n-hexane were purchased from Carl Roth. A Grubbs second-generation catalyst was purchased from Sigma-Aldrich; it was reacted with pyridine to form a Grubbs third-generation catalyst using a previously reported procedure.^{26 (link) 1}H NMR spectra were recorded on a Bruker 250 MHz spectrometer (Bruker, Madison, WI) to confirm the molecular structure of the oxonorbornene monomers and polymers. The molecular mass and mass distribution of the polymers were studied by gel permeation chromatography (GPC) using an Agilent GPC system with chloroform as eluent, PSS SDV columns (PSS, Mainz, Germany), and poly(methyl methacrylate) standards.

Zheng Z., Saar J., Zhi B., Qiu T.A., Gallagher M.J., Fairbrother D.H., Haynes C.L., Lienkamp K, & Rosenzweig Z. (2018). Structure–Property Relationships of Amine-rich and Membrane-Disruptive Poly(oxonorbornene)-Coated Gold Nanoparticles. Langmuir : the ACS journal of surfaces and colloids, 34(15), 4614-4625.

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Grubbs Catalyst Polymerization Protocol

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The Grubbs first-generation catalyst [benzylidene-bis(tricyclohexylphosphino)-dichlororuthenium], 1, Grubbs second-generation catalyst [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphino)ruthenium], 2, and other solid reagents and solvents used in this study
were purchased from Sigma-Aldrich and were used without further purification.
Solvents were dried through a small column of activated neutral alumina
(10% v/v) prior to use. All of the preparations were carried out under
Schlenk conditions or in a glovebox.

Swart M.R., Marais C, & Erasmus E. (2021). Comparison of the Spectroscopically Measured Catalyst Transformation and Electrochemical Properties of Grubbs’ First- and Second-Generation Catalysts. ACS Omega, 6(43), 28642-28653.

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Synthesis of Functionalized Norbornene Derivatives

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Example 1

Materials: The following materials were purchased and used as received.

Dimethyl 5-norbornene-2,3-dicarboxylate (C3) was purchased from Alfa Aesar,

Dichloromethane (DCM) was stored over activated Alumina and purged with Argon before use, Isopropyl alcohol (IPA), dicyclopentadiene (DCPD), 1H,1H,2H-Perflouro-1-octene (PF6), 1H,1H,2H-Perflouro-1-dodecene (PF10), toluene, thionyl chloride, ethylacetate, dimethylformamide (DMF), Maleimide, furan, diisopropylazodicarboxylate (DIAD), triphenylphosphine (Ph₃P), 1-haxadecanol, tetrahydrofuran (THF), ethyl acetate, N-phenylMaleimide, acetonitrile, methanol, Grubbs second generation catalyst, 3-bromopyridine, and pentane were obtained from Sigma-Aldrich Co. and used without further treatment. Dichloropentane, also obtained from Sigma-Aldrich Co., was treated with basic alumina before use. Cyclooctadiene (COD) was purified by vacuum distillation from boron trifluoride and used fresh.

US10213750B2. Hydrophilically modified fluorinated membrane (I) (2019-02-26). Pall Corporation [US]. Inventors: Khaled Abdel-Hakim Helmy Aamer [US], Jian Qiu [US], Hassan Ait-Haddou [US].

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Synthesis of Norbornene-Functionalized ROMP BBNs

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ROMP BBNs were synthesized by polymerizing norbornene-functionalized macromonomers (250 mg) with varied amounts of cross-linker. BBNs were all polymerized using either Grubbs’ second-generation catalyst (Sigma) or Grubbs’ third-generation catalyst at varied M/Is. For a typical reaction, the macromonomer and cross-linker were first dissolved in 1 mL of dried dichloromethane (DCM) in a 20 mL vial before adding 1 mL of catalyst/DCM solution. The reaction was allowed to run overnight before being quenched with three drops of ethyl vinyl ether (EVE, Sigma). Grubbs’ third-generation catalyst was synthesized using 2-bromopyridine from published protocols.³⁶

Nakada Y., Jiang Y., Nishijyo T., Itoh Y, & Lu C.D. (2001). Molecular Characterization and Regulation of the aguBA Operon, Responsible for Agmatine Utilization in Pseudomonas aeruginosa PAO1. Journal of Bacteriology, 183(22), 6517-6524.

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Organometallic Heterocycle Synthesis

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Furan, maleic anhydride, 3-bromopropylamine hydrobromide, 1-bromohexane, 3-aminomethyl pyridine, triphenylphosphine, cysteamine, hydrogen tetrachloroaurate(III), sodium borohydride, ethylvinyl ether, 3-bromopyridine, acetic anhydride, petroleum ether, diethyl ether,
N,N-dimethylformamide (DMF),
N,N-dimethylacetamide (DMAc), dichloromethane (DCM), chloroform, pentane, dimethyl sulfoxide (DMSO) were purchased from Sigma Aldrich and used as received. Ethyl acetate and hexane were distilled by conventional techniques. Grubbs second generation catalyst was purchased from Sigma Aldrich. Grubbs third generation catalyst [(H₂-Imes)(3-Br-py)₂-(Cl)₂Ru=CHPh] was freshly prepared according to the previously reported procedure [38]. Phosphate buffered saline (PBS) was obtained from Sigma Aldrich in tablet form. Mueller–Hinton broth (MHB) and Mueller–Hinton agar (MHA) media (both from Dıfco, BD Diagnostic Systems, United States) were used for microbiological tests.
Staphylococcus aureusATCC 25923 strain and
Escherichia coliATCC 25922 strain were acquired from the department of Molecular Biology and Genetics Department (Yildiz Technical University, Turkey) and used as representative of Gram-positive and Gram-negative bacteria, respectively (ATCC is the registered trademark of American Type Culture Collection).

SÜER N.C., ARASOĞLU T., CANKURTARAN H., OKUTAN M., GALLEI M, & EREN T. (2021). Detection of bacteria using antimicrobial polymer derived via ring-opening metathesis (romp) pathway. Turkish Journal of Chemistry, 45(4), 986-1003.

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Synthesis and Characterization of PEG-based Nanomaterials

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Methoxy-PEG-amine (750 Da and 2 kDa), methoxy PEG (5 kDa), albumin–fluorescein isothiocyanate (BSA-FITC), and Grubbs second-generation catalyst were purchased from Sigma-Aldrich while Methoxy-PEG-amine, HCl salt (3 kDa) was obtained from JenKem Technology USA. DiO dye (3,3′-dioctadecyloxacarbocyanine perchlorate) was purchased from Biotium and poly(lactic acid) (6.7 kDa and 14.3 kDa) from LACTEL. PEG-MM^{30 (link)} and N-(hydroxyethyl)-cis-5-norbornene-exo-2,3-dicarboximide^{55 (link)} were prepared according to previously reported procedures. All other solvents and reagents were purchased from commercial suppliers and used without additional purification unless otherwise noted.

Grundler J., Shin K., Suh H.W., Zhong M, & Saltzman W.M. (2021). Surface Topography of Polyethylene Glycol Shell Nanoparticles Formed from Bottlebrush Block Copolymers Controls Interactions with Proteins and Cells. ACS nano, 15(10), 16118-16129.

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