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Chemical Structure| 52490-94-5
Chemical Structure| 52490-94-5
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Product Details of [ 52490-94-5 ]

CAS No. :52490-94-5 MDL No. :MFCD28144560
Formula : C28H29Cl2PRu Boiling Point : -
Linear Structure Formula :- InChI Key :ZMCNSVXDEFGLMT-UHFFFAOYSA-L
M.W : 568.48 Pubchem ID :121237570
Synonyms :

Safety of [ 52490-94-5 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P261-P270-P271-P264-P280-P362+P364-P301+P312+P330-P302+P352+P312-P304+P340+P312 UN#:
Hazard Statements:H302+H312+H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 52490-94-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 52490-94-5 ]

[ 52490-94-5 ] Synthesis Path-Downstream   1~85

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YieldReaction ConditionsOperation in experiment
91.3% In dichloromethane; at 20℃; for 17h;Schlenk technique; Inert atmosphere; A solution of [(p-cymene)RuCl 2 ] 2 (100 mg, 100 mol%, 0.16 mmol) and PPh 3 (90 mg, 210 mol%, 0.34 mmol) in CH 2 Cl 2 (6 ml) was stirred at room temperature in Schlenk tube under argon at- mosphere for 17 h. After this time the solution was reduced in vac- uum to ~1,5 ml. Hexanes (~8 ml) were added to yield an orange precipitate. Then it was filtered through a funnel with fritted disc. The solid was washed with hexanes (3 ml 3 times) and dried in vacuum to yield a red-brown solid (169.6 mg, 91.3% yield). 1 H NMR (400 MHz, CDCl 3 ) 7.87 -7.73 (m, 6H), 7.42 -7.28 (m, 9H), 5.18 (d, J = 5.9 Hz, 2H), 4.98 (d, J = 5.9 Hz, 2H), 2.84 (sept, J = 6.9 Hz, 1H), 1.85 (s, 3H), 1.08 (d, J = 6.9 Hz, 6H). 13 C NMR (101 MHz, CDCl 3 ) 134.4 (d, J = 9.3 Hz), 133.9 (d, J = 45.6 Hz), 130.3 (d, J = 2.4 Hz), 128.0 (d, J = 10.0 Hz), 111.2, 96.0, 89.1 (d, J = 3.2 Hz), 87.2 (d, J = 5.5 Hz), 30.3, 21.9, 17.8. 31 P NMR (162 MHz, CDCl 3 ) 24.2.
84% In toluene; for 1h;Inert atmosphere; Schlenk technique; Reflux; To a suspension of [Ru(p-cymene)Cl2]2 (100 mg, 0.163 mmol) in toluene (5 mL), triphenylphosphine (0.36 mmol, 2.2 equiv) was added at room temperature. The resulting mixture was heated to reflux for 1 h. After the mixture was cooled, the precipitate was filtered, washed with hexane (3×5 mL), and dried in vacuum, affording an orange solid (155.6 mg, 84%). 1H NMR (400 MHz, CD3Cl): δ=1.10 (d, J=6.1Hz, 6H), 1.80 (s, 3H), 2.80 (m, 1H), 4.92 (d, J=5.8Hz, 2H), 5.12 (d, J=5.8Hz, 2H), 7.20, 7.30, 7.76 (m, 15H); 13C NMR (400 MHz, CDCl3): δ=17.38, 21.52, 29.88, 86.78, 88.70, 95.62, 110.78, 127.54, 129.85, 134.03.
82% In hexane; for 5h;Reflux; 2.3.2.1 Synthesis of [RuIICl2(p-cymene)PPh3] (3) A suspension of (1) (0.55 g, 0.9 mmol) and PPh3 (0.6 g, 2.25 mmol) in hexane (30 ml) was heated under reflux during 5 h, keeping the stirring until it reached room temperature. The red precipitate result was filtered off, washed with hexane and dried under reduced pressure. Yield: 82%; M.S.[ESI]: m/z 586.1 {M-Cl}+; Anal. Calc. C28H29Cl2Ru: 59.16% C, 5.14% H; Anal. Exp.: 58.83% C, 5.04% H; 1H NMR [CDCl3]: δ 7.37-7.83 (m, 15H, PPh3), δa 5.18, δb 4.99 (2d, J(HH) ≈ 6.0 Hz, 4H, C-H{ring}), δ 2.85 (sep, J(HH) ≈ 7.0 Hz, H, CH(Me)2), δ 1.87 (s, 3H, CH3{ring}), δ 1.11 (d, J(HH) ≈ 7.0 Hz, 6H, CH(Me)2); 31P{1H}NMR [CDCl3]: δ 24.16 (s, PPh3); IR: 1091.21 (νP-C), 520.95 (πC-P-C).
79.2% In dichloromethane; for 3h;Reflux; Dichloro(p-cymene)ruthenium(II) dimer (0.509 g, 8.31 x 10-4 mol)was measured and added to triphenylphosphine (3.268 g, 1.25 x 10-2mol) in a round bottomed flask. Dichloromethane (50 mL) was added tothis vessel, and the reaction mixture was stirred under reflux (50 C) for3 h. No colour change occurred across the duration of this reaction,remaining a transparent dark red solution throughout. The solvent wasremoved in vacuo at 40 C to a highly concentrated solution (∼8 mL). Diethyl ether (50 mL) was added to this solution, causing the product toprecipitate out of solution, and the supernatant was subsequently decantedoff. This was repeated four more times until the decanted supernatantwas colourless. A dark red crystalline material was obtained,and was allowed to air dry for 1 h before proceeding with analysis andfurther reactions. A yield of 0.748 g (1.32 x 10-3 mol, 79.2%) was recorded.
76% In tetrahydrofuran; at 20℃; for 3h;Inert atmosphere; General procedure: A 50-mL round-bottom flask was charged with [Ru(p-cymene) (0.2029 g, 0.331 mmol) and CH2Cl2(20 mL). To the orange solution was added P(C6H4F)3 (0.2199 g, 0.695 mmol), and the mixture was leftto stir for 3 h at room temperature. The volatiles were removed in vacuo to leave a dark red oil, andhexanes were added to precipitate a solid product. The resulting orange solid was collected by vacuumfiltration and dried in vacuo (0.3529 g, 86% yield).
In ethanol; at -20℃; for 32h;Inert atmosphere; Reflux; Synthesis 3 - Preparation of Dichloro(p-cymene)(triphenylphosphine)ruthenium[RuCl2(cymene)]2 was be added as a suspension in ethanol to a solution of 7 equivalents of the triphenylphosphine, also in ethanol. The mixture would be refluxed for 16 hours before the volume of the reaction was reduced by half in vacuo, filtered to remove excess phosphine and then chilled for 16 hours at -20C. The product crystallized out of the cold ethanol and was washed with hexane.The product was analysed by lH NMR (CDC13): 57.83 (m, 6H, PPh3), 57.37 (m, 9H, PPh3), 55.20 (d,2H, 6.23Hz), 54.99 (d, 2H, J=6.23Hz), 52.86 (septet, 1H, J=6.96Hz), 51.87 (s, 3H), 51.10 (d, 6H, J=6.96Hz). 31P NMR (CDCI3) 524.8 (s)
In ethanol; at -20℃; for 32h;Reflux; Synthesis 3Preparation ofDichloro(p-cymene)(triphenylphosphine)ruthenium10115] [RuC12(cymene)]2 was be added as a suspension in ethanol to a solution of 7 equivalents of the triphenylphosphine, also in ethanol. The mixture would be refluxed for 16 hours before the volume of the reaction was reduced by half in vacuo, filtered to remove excess phosphine and then chilled for 16 hours at -20 C. The product crystallized out of the cold ethanol and was washed with hexane.10116] The product was analysed by ‘H NMR (CDC13):ö7.83 (m, 6H, PPh3), ö7.37 (m, 9H, PPh3), ö5.20 (d, 2H, J=6.23 Hz), ö4.99 (d, 2H, J=6.23 Hz), ö2.86 (septet, 1H, J=6.96 Hz), ö1 .87 (s, 3H), ö1 .10 (d, 6H, J=6.96 Hz). 3’P NMR (CDC13) ö24.8 (s)
In methanol; for 2h;Heating; Inert atmosphere; Schlenk technique; A solution of 1.00 g of RuCl3·3H2O dissolved in methanol with 5 mL of α-phellandrene wasmaintained under reux during 5 h (see Figure 1). The solution was concentrated and theobtained dark red precipitate [(6-p-cymene)2Ru2Cl4] (a) was ltered o and vacuum dried[32]. The red solid [(6-p-cymene)Ru(PPh3)Cl2] (b) was obtained by placing 850 mg of a inmethanol with 804 mg of PPh3 under reduced pressure during 2 h. To 200 mg of b in 10 mLof toluene were added 121 mg of NH4PF6 and 3 mL of ethanol. The solution was stirred,slightly warmed for 10 min, and added by 132 mg of dppb. This solution was placed underreux for 3 h. Subsequently, the solution was cooled and the obtained yellow solid was lteredo, washed with diethylether, and vacuum dried. Yield: 76%.

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  • tetraphenylphosphonium tetrathiotungstate [ No CAS ]
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  • (4-methylisopropylbenzene)RuWS4(triphenylphosphine) [ No CAS ]
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  • sodium hexaflorophosphate [ No CAS ]
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  • {Ru(=C(OMe)CH2Ph)Cl(PPh3)(η6-p-cymene)}PF6 [ No CAS ]
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  • ammonium hexafluorophosphate [ No CAS ]
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  • ammonium hexafluorophosphate [ No CAS ]
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  • 1-phenyl-2-(diphenylphosphino)propanone [ No CAS ]
  • ((C6H5)2PCH(CH3)C(C6H5)O)2(P(C6H5)3)RuCl(1+)*PF6(1-)*0.5CH2Cl2=[((C6H5)2PCH(CH3)C(C6H5)O)2(P(C6H5)3)RuCl](PF6)*0.5CH2Cl2 [ No CAS ]
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  • [(cymene)ClRu(μ-Cl)3Ru((CH2)4(P(C6H5)2)2)]*(CH3)2CO [ No CAS ]
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  • ammonium hexafluorophosphate [ No CAS ]
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  • [[Ru(η6-p-cymene)Cl(PPh3)]2(μ-1,4-dicyanamidobenzene)](PF6)2 [ No CAS ]
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  • [[Ru(η6-p-cymene)Cl(PPh3)]2(μ-N,N'-dicyano-4-4'-diaminobiphenyl)](PF6)2 [ No CAS ]
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  • ammonium hexafluorophosphate [ No CAS ]
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  • trans,trans,trans-RuCl2(CO)(PPh3)[η2-Ph2PCH2C(tBu)=O]*2/3CH2Cl2 [ No CAS ]
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  • sodium hexaflorophosphate [ No CAS ]
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  • [(η6-p-cymene)RuClPPh3]2(μ-4,4'-bipyridine)(BF4)2 [ No CAS ]
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  • [Ru(OCOC(CH2)NCOCH3)(CH3C6H4CH(CH3)2)(P(C6H5)3)]*CHCl3 [ No CAS ]
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  • 2-(N-acetylamino)cinnamic acid [ No CAS ]
  • [Ru(OCOC(CHC6H5)NCOCH3)(CH3C6H4CH(CH3)2)(P(C6H5)3)]*2.5CHCl3 [ No CAS ]
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  • ammonium hexafluorophosphate [ No CAS ]
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  • [(η(6)-p-cymene)Ru(PPh3)(1,2-phenylenediamine)](BF4) [ No CAS ]
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  • tin(ll) chloride [ No CAS ]
  • [(η(6).-cymene)Ru(SnCl3)Cl(triphenylphosphine)] [ No CAS ]
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  • ammonium hexafluorophosphate [ No CAS ]
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  • [(η6-p-cymeme)RuCl(PPh3)(η1-PPh2CCPPh2)]PF6*0.75CH2Cl2 [ No CAS ]
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  • ammonium hexafluorophosphate [ No CAS ]
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YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 70℃; for 16h;Sealed vial;Product distribution / selectivity; In-Situ Preparations of Olefin Metathesis Catalysts Using 1-(3,5-Dimethoxyphenyl)-1-Phenylprop-2-yn-1-ol Method 1 : A small conical vial equipped with a spin vane was charged with RuCkip- cymene)(PCy3) (50 mg, 0.085 mmol) and l-(3,5-dimethoxyphenyl)-l-phenylprop-2-yn-l -ol (5) (25 mg, 0.094 mmol, 1.1 equiv). THF was added to reach a total volume of 1.0 mL of dark orange solution. The vial was sealed, removed from the glove box, and heated at 70 C under stirring for 16 hours. The dark brown solution was used as is to catalyze ring-closing metathesis (RCM) reactions (see below). The dark brown solution features two main phosphorus-containing species in a -5/1 ratio according to 31P NMR spectroscopy. Major species: 3 lP{lH} NMR (THF-d8): δ 48.6 (s). Minor species: 31P{.H} NMR (THF-d8): δ 68.1 (s).
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  • ammonium hexafluorophosphate [ No CAS ]
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  • [ 209854-68-2 ]
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  • C79H106N13O16Pol [ No CAS ]
  • C107H136ClN13O16PRu [ No CAS ]
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  • [ 52490-94-5 ]
  • [ 7732-18-5 ]
  • [ 298-14-6 ]
  • Ru(2-O2CO)(PPh3)(p-cymene)*H2O [ No CAS ]
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  • [ 1609198-84-6 ]
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  • [ 75-09-2 ]
  • C29H36Cl3N3Ru2*0.5CH2Cl2 [ No CAS ]
  • [ 603-35-0 ]
  • [ 52490-94-5 ]
  • C19H22ClN3Ru*CH2Cl2 [ No CAS ]
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  • [ 5344-27-4 ]
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  • [RuIICl(p-cymene)(4-(2-EtOH))PPh3][PF6] [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With ammonium hexafluorophosphate; In methanol; for 19h;Reflux; A suspension of (3) (0.1 g, 0.18 mmol), NH4PF6 (0.03 g, 0.2 mmol) and <strong>[5344-27-4]4-(2-hydroxyethyl)pyridine</strong> (300 mul, 2.7 mmol) in methanol (30 ml) was heated under reflux during 7 h, keeping the stirring afterwards during 12 h more at room temperature. Solvent was removed under reduced pressure until a yellow oil was obtained. After the addition of some drops of DMSO, a brown precipitate was obtained with the addition of H2O. The precipitate obtained was filtered off, washed with deionized water and dried under reduced pressure. Yield: 69%; M.S.[ESI]: m/z 656.14 {M+}; Anal. Calc. C35H38ClF6NOP2Ru-NH4: 48.67% C, 4.74% H, 3.66% N; Anal. Exp.: 49.16% C, 4.66%, 3.57% N; 1H NMR [CDCl3]: delta 8.73 (d, J(HH) ? 6.3 Hz, 2H, C-H{4-(2-EtOH)Py}), delta 7.27-7.50 (m, 15H, PPh3), delta 7.02 (d, J(HH) ? 6.3 Hz, 2H, C-H{4-(2-EtOH)Py}), delta 5.93-5.25 (4d, J(HH) ? 6.0 Hz, 4H, C-H{ring}), delta 3.77 (m, J(HH) ? 7.0 Hz, 2H, CH2{4-(2-EtOH)Py}), delta 2.76 (t, J(HH) ? 6.0 Hz, 2H, CH2{4-(2-EtOH)Py}), delta 2.24 (sep, J(HH) ? 7.0 Hz, H, CH(Me)2), delta 1.66 (s, 3H, CH3{ring}), delta 1.10 (d, J(HH) ? 7.0 Hz, 6H, CH(Me)2); 31P{1H}NMR [CDCl3]: delta 37.1 (s, PPh3), delta - 144.1 (sep, J(PF) ? 713 Hz, PF6-), 19F{1H}NMR [CDCl3]: delta - 73 (d, J(FP) ? 713 Hz, PF6-); IR: 3533.84 (nuOH), 1093.69 (nuP-C), 840.42 (nuRu-N), 700.86 (nuP-F).
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YieldReaction ConditionsOperation in experiment
78% In methanol; at 35℃; for 2h; 2.3.2.6 Synthesis of [RuIICl(p-cymene)(PPh3)2][PF6] (8) A suspension of (3) (0.1 g, 0.18 mmol), KPF6 (0.04 g, 0.2 mmol) and PPh3 (0.1 g, 0.4 mmol) in methanol (30 ml) was stirred during 2 h at 35 C. Solvent was removed at room temperature under reduced pressure until a yellow oil was obtained. With the addition of hexane a yellow precipitate was obtained, which was filtered off, washed with ethanol/hexane 1:2 and dried under reduced pressure. Yield: 78%; M.S.[ESI]: m/z 795.16 {M+}; Anal. Calc. C46H44ClF6P3Ru: 58.76% C, 4.72% H; Anal. Exp.: 58.56% C, 4.79% H; 1H NMR [CDCl3]: δ 7.45-7.22 (m, 30H, 2PPh3), δ 5.60-5.00 (2d, J(HH) ≈ 6.4 Hz, 4H, C-H{ring}), δ 2.70 (sep, J(HH) ≈ 7.0 Hz, H, CH(Me)2), δ 1.22 (d, J(HH) ≈ 7.0 Hz, 6H, CH(Me)2), δ 1.10 (s, 3H, CH3{ring}); 31P{1H}NMR [CDCl3]: δ 20.67 (s, PPh3), δ - 144.1 (sep, J(PF) ≈ 713 Hz, PF6-), 19F{1H}NMR [CDCl3]: δ - 73 (d, J(FP) ≈ 713 Hz, PF6-); IR: 1089.04 (νP-C), 831.44 (νRu-N), 699.03 (νP-F), 516.46 (πC-P-C).
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  • [RuIICl(p-cymene)(3-picoline)PPh3][PF6] [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In methanol; at 20℃; for 24h; A suspension of (3) (0.1 g, 0.18 mmol), KPF6 (0.04 g, 0.2 mmol) and3-methylpyridine (3-picoline, 400 μl, 4.0 mmol) in methanol (30 ml)was stirred during 24 h at room temperature. Solvent was removedunder reduced pressure until a yellow oil was obtained.With the additionof diethyl ether a yellow precipitate was obtained, which wasfiltered off, washed with diethyl ether and dried under reducedpressure.Yield: 78%;M.S.[ESI]: m/z 626.13 {M+}; Anal. Calc. C34H36ClF6NP2Ru:52.96% C, 4.71% H, 1.82% N; Anal. Exp.: 53.13% C, 4.83, 1.82% N; 1HNMR[CDCl3]: δ 8.76 (d, J(HH)≈5.0 Hz, H, C-H{3-picoline}), δ 8.53 (s, H,C-H{3-picoline}), δ 7.27-7.57 (m, 16H, PPh3, 3-picoline), δ 7.04 (d, J(HH)≈ 2.0 Hz, H, C-H{3-picoline}), δ 5.95-5.30 (4d, J(HH) ≈ 5.0 Hz, 4H,C-H{ring}), δ 2.18 (sep, J(HH) ≈ 6.4 Hz, H, CH(Me)2), δ 2.12 (s, 3H,CH3{3-picoline}), δ 1.65 (s, 3H, CH3{ring}), δ 1.10 (2d,J(HH) ≈ 7.0 Hz, 6H, CH(Me)2); 31P{1H}NMR [CDCl3]: δ 37.3 (s, PPh3),δ -144.1 (sep, J(PF) ≈ 713 Hz, PF6-), 19F{1H}NMR [CDCl3]: δ -73(d, J(FP) ≈ 713 Hz, PF6-); IR: 1093.02 (νP-C), 840.39 (νRu-N), 700.75(νP-F).
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  • [RuIICl(p-cymene)(3-picoline)PPh3][PF6] [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In methanol; at 20℃; for 19h;Reflux; A suspension of (3) (0.1 g, 0.18 mmol), KPF6 (0.04 g, 0.2 mmol) and 3,4-dimethylpyridine (3,4-lutidine, 200 μl, 1.8 mmol) in methanol (30 ml)was heated under reflux during 7 h, keeping the stirring afterwardsduring 12 h more at room temperature. Solvent was removed underreduced pressure until an orange oil was obtained. With the additionof diethyl ether an orange precipitate was obtained, which was filteredoff, washed with diethyl ether and dried under reduced pressure.Yield: 84%;M.S.[ESI]:m/z 640.15 {M+}; Anal. Calc. C35H38ClF6NP2Ru-H2O: 52.34 %C, 5.02% H, 1.74% N; Anal. Exp.: 52.39% C, 4.60% H, 1.84% N;1H NMR [CDCl3]: δ 8.60 (d, J(HH)≈5.3 Hz, H, C-H{3,5-lutidine}), δ 8.35(s, H, C-H{3,5-lutidine}), δ 7.26-7.5 (m, 15H, PPh3), δ 6.90 (d, J(HH)≈ 5.3 Hz, H, C-H{3,5-lutidine}), δ 5.98-5.28 (4d, J(HH) ≈ 5.7 Hz, 4H,C-H{ring}), δ 2.21 (sep, J(HH) ≈ 7.0 Hz, H, CH(Me)2), δ 2.15 (s, 3H,CH3{3,5-lutidine}), δ 1.99 (s, 3H, CH3{3,5-lutidine}), δ 1.64 (s, 3H, CH3{ring}), δ 1.11 (2d, J(HH) ≈ 5.0 Hz, 6H, CH(Me)2); 31P{1H}NMR[CDCl3]: δ 37.7 (s, PPh3), δ -144.1 (sep, J(PF) ≈ 713 Hz, PF6-), 19F{1H}NMR [CDCl3]: δ -73 (d, J(FP) ≈ 713 Hz, PF6-); IR: 1092.35 (νP-C),840.39 (νRu-N), 700.30 (νP-F).
  • 58
  • [ 17084-13-8 ]
  • [ 591-22-0 ]
  • [ 52490-94-5 ]
  • [RuIICl(p-cymene)(3-picoline)PPh3][PF6] [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% In methanol; at 20℃; for 19h;Reflux; A suspension of (3) (0.1 g, 0.18 mmol), KPF6 (0.04 g, 0.2 mmol) and 3,4-dimethylpyridine (3,4-lutidine, 200 μl, 1.8 mmol) in methanol (30 ml)was heated under reflux during 7 h, keeping the stirring afterwardsduring 12 h more at room temperature. Solvent was removed underreduced pressure until an orange oil was obtained. With the additionof diethyl ether an orange precipitate was obtained, which was filteredoff, washed with diethyl ether and dried under reduced pressure.Yield: 84%;M.S.[ESI]:m/z 640.15 {M+}; Anal. Calc. C35H38ClF6NP2Ru-H2O: 52.34 %C, 5.02% H, 1.74% N; Anal. Exp.: 52.39% C, 4.60% H, 1.84% N;1H NMR [CDCl3]: δ 8.60 (d, J(HH)≈5.3 Hz, H, C-H{3,5-lutidine}), δ 8.35(s, H, C-H{3,5-lutidine}), δ 7.26-7.5 (m, 15H, PPh3), δ 6.90 (d, J(HH)≈ 5.3 Hz, H, C-H{3,5-lutidine}), δ 5.98-5.28 (4d, J(HH) ≈ 5.7 Hz, 4H,C-H{ring}), δ 2.21 (sep, J(HH) ≈ 7.0 Hz, H, CH(Me)2), δ 2.15 (s, 3H,CH3{3,5-lutidine}), δ 1.99 (s, 3H, CH3{3,5-lutidine}), δ 1.64 (s, 3H, CH3{ring}), δ 1.11 (2d, J(HH) ≈ 5.0 Hz, 6H, CH(Me)2); 31P{1H}NMR[CDCl3]: δ 37.7 (s, PPh3), δ -144.1 (sep, J(PF) ≈ 713 Hz, PF6-), 19F{1H}NMR [CDCl3]: δ -73 (d, J(FP) ≈ 713 Hz, PF6-); IR: 1092.35 (νP-C),840.39 (νRu-N), 700.30 (νP-F).
  • 59
  • [ 6629-04-5 ]
  • [ 52490-94-5 ]
  • [ 1615243-50-9 ]
  • 60
  • [ 52490-94-5 ]
  • [ 533-75-5 ]
  • [(η6-p-Cymene)Ru(κ2-O,O-tropolone)PPh3]Cl [ No CAS ]
  • 61
  • [ 100928-22-1 ]
  • [ 603-35-0 ]
  • [ 52490-94-5 ]
  • 62
  • [ 52490-94-5 ]
  • 3C23H30N6*3C14H17N3O3 [ No CAS ]
  • [ 2923-28-6 ]
  • ME3·[BA{Ru(p-cymene)(PPh3)Cl}+]3·3CF3SO3- [ No CAS ]
  • 63
  • [ 52490-94-5 ]
  • [ 101547-20-0 ]
  • C41H34Cl2P2Ru [ No CAS ]
  • 64
  • [ 52490-94-5 ]
  • [ 101547-20-0 ]
  • [ 143-66-8 ]
  • C15H18ClRu(1+)*C24H20B(1-) [ No CAS ]
  • 65
  • [ 52490-94-5 ]
  • [ 218900-77-7 ]
  • C54H64Cl3GePRu [ No CAS ]
  • 66
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 52490-94-5 ]
  • [ 7688-25-7 ]
  • [(η6-p-cymene)Ru(1,4-bis(diphenylphosphine)butane)Cl]PF6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In ethanol; toluene;Inert atmosphere; Schlenk technique; Reflux; A solution of 1.00 g of RuCl3·3H2O dissolved in methanol with 5 mL of α-phellandrene wasmaintained under reux during 5 h (see Figure 1). The solution was concentrated and theobtained dark red precipitate [(6-p-cymene)2Ru2Cl4] (a) was ltered o and vacuum dried[32]. The red solid [(6-p-cymene)Ru(PPh3)Cl2] (b) was obtained by placing 850 mg of a inmethanol with 804 mg of PPh3 under reduced pressure during 2 h. To 200 mg of b in 10 mLof toluene were added 121 mg of NH4PF6 and 3 mL of ethanol. The solution was stirred,slightly warmed for 10 min, and added by 132 mg of dppb. This solution was placed underreux for 3 h. Subsequently, the solution was cooled and the obtained yellow solid was lteredo, washed with diethylether, and vacuum dried. Yield: 76%. Anal. Calcd forC38H42ClF6P3Ru·H2O; C, 53.06; H, 5.16. Found: C, 53.49; H, 4.74. IR (KBr, cm-1): ν(C-H), 3069;ν(C=C), 1479; ν(P-F), 841; ν(Ru-P), 512; ν(Ru-Cl), 295. 1H NMR [(CD3)2CO], δ(ppm) (m, I):7.73-7.53 (m, 20H, Phdppb), 6.06 (d, 2H, JHH = 5.18 Hz, 3-CHp-cymene), 5.31 (d, 2H, JHH = 5.35 Hz,4-CHp-cymene), 3.56 (m, 2H, a-CH2dppb), 2.62 (sep, 1H, JHH = 6.91 Hz, 6-CHp-cymene). 2.27 (m, 2H,d-CH2dppb), 1.94 (m, 2H, b-CH2dppb), 1.59 (m, 2H, c-CH2dppb), 1.19 (s, 3H, 1-CH3p-cymene), 1.04(d, 6H, JHH = 6.95 Hz, 7-CH3p-cymene). 31P{1H} NMR [(CD3)2CO] δ(ppm) (m, I): 31.19 (s, dppb),-144.10 (sep, PF6). 13C{1H} NMR [(CD3)2CO] δ(ppm) (m, I): 134.12 (t, CH-Phdppb), 132.81(t, CH-Phdppb), 132.46 (s, C-Phdppb), 131.31 (s, C-Phdppb), 129.94 (t, CH-Phdppb), 129.32(t, CH-Phdppb), 99.23 (s, C-2p-cymene), 97.05 (s, CH-3p-cymene), 91.76 (s, CH-4p-cymene), 31,27(s, CH-6p-cymene), 30.25 (s, a-CH2dppb), 28.31 (s, d-CH2dppb), 28.21 (s, b-CH2dppb), 28.12 (s, c-CH2dppb),23.28 (s, CH3-7p-cymene), 21.35 (s, CH3-7p-cymene), 15,29 (s, CH3-1p-cymene).
  • 67
  • [ 52490-94-5 ]
  • [(η6-p-cymene)Ru(μ-Cl)3RuCl2(κP-PPh3)] [ No CAS ]
  • 68
  • [Ru(κ<SUP>2</SUP>O,O'-salCO<SUB>2</SUB>)(PPh<SUB>3</SUB>)(η<SUP>6</SUP>-p-cymene)] [ No CAS ]
  • [ 7647-14-5 ]
  • [ 52490-94-5 ]
YieldReaction ConditionsOperation in experiment
In dimethylsulfoxide-d6; water-d2; at 37℃; for 72h; General procedure: DMSO-d6/D2O 9:1 v/v or DMSO-d6/D2O 9:1 v/v + NaCl (0.11 M) solutions were used for the stability experiments. Dimethyl sulfone (Me2SO2, 5.610-3 M) was added to each solutionas a reference for 1H NMR spectra (δ = 2.97 ppm in DMSO-d6/D2O9:1) [39]. Complexes 1-3 and 5 were dissolved in the selectedDMSO-d6/D2O mixture (0.6 mL; [Ru] = 1.510-2 M) and the resultingorange solutions were analyzed by 1H/31P{1H} NMR shortlythereafter (t < 10 min). The solutions were then maintained at 37 Cfor 72 h and periodically analysed by NMR upon brief cooling toroom temperature. Results are compiled in Tables 2 and 3; percentvalues of compounds in solution are based on 1H NMR spectroscopyand refer to identified compounds only.
  • 69
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 52490-94-5 ]
  • [ 314746-86-6 ]
  • C39H39ClN2O3PRuS(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: The precursors and acylthiourea ligands were synthesized according to previous reports [25,50,51].The acylthiourea ligand (0.190 mmol) was added to 50 mL of methanolic solution of [Ru(η6-p-cymene)(PPh3)Cl2] (0.180 mmol; 0.100 g). The mixture was kept under inert atmosphere and was stirred for 1 h and then NH4PF6 (0.300 mmol; 0.050 g) was added. The reaction mixture was concentrated under reduced pressure, until precipitation of an orange solid. The solid was filtered off, washed with water (3 * 5 mL), cold methanol (3 * 5 mL) and dried under vacuum.
  • 70
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 52490-94-5 ]
  • [ 314746-86-6 ]
  • C39H38N2O3PRuS(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: The acylthiourea ligand (0.190 mmol) was dissolved in 25 mL methanolicsolution of [Ru(η-6-p-cymene)(PPh3)Cl2] (0.180 mmol;0.100 g). After stirring for 0.5 h, under inert atmosphere, 25 mL ofdeaerated water was added. The mixture was kept under inert atmosphereand reflux, and was stirred for 3 h. For precipitation of a yellowsolid, NH4PF6 (0. 300 mmol; 0.050 g) was added. The solid was filteredoff, washed with water (3×5 mL) and dried under vacuum.
  • 71
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 52490-94-5 ]
  • N-(2-thiophenecarbonyl)-N’-(2-thiophenemethyl)thiourea [ No CAS ]
  • C39H39ClN2OPRuS3(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: The precursors and acylthiourea ligands were synthesized according to previous reports [25,50,51].The acylthiourea ligand (0.190 mmol) was added to 50 mL of methanolic solution of [Ru(η6-p-cymene)(PPh3)Cl2] (0.180 mmol; 0.100 g). The mixture was kept under inert atmosphere and was stirred for 1 h and then NH4PF6 (0.300 mmol; 0.050 g) was added. The reaction mixture was concentrated under reduced pressure, until precipitation of an orange solid. The solid was filtered off, washed with water (3 * 5 mL), cold methanol (3 * 5 mL) and dried under vacuum.
  • 72
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 52490-94-5 ]
  • N-(2-thiophenecarbonyl)-N’-(2-furfuryl)thiourea [ No CAS ]
  • C39H39ClN2O2PRuS2(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: The precursors and acylthiourea ligands were synthesized according to previous reports [25,50,51].The acylthiourea ligand (0.190 mmol) was added to 50 mL of methanolic solution of [Ru(η6-p-cymene)(PPh3)Cl2] (0.180 mmol; 0.100 g). The mixture was kept under inert atmosphere and was stirred for 1 h and then NH4PF6 (0.300 mmol; 0.050 g) was added. The reaction mixture was concentrated under reduced pressure, until precipitation of an orange solid. The solid was filtered off, washed with water (3 * 5 mL), cold methanol (3 * 5 mL) and dried under vacuum.
  • 73
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 52490-94-5 ]
  • N-(2-furoyl)-N’-piperonylthiourea [ No CAS ]
  • C42H41ClN2O4PRuS(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: The precursors and acylthiourea ligands were synthesized according to previous reports [25,50,51].The acylthiourea ligand (0.190 mmol) was added to 50 mL of methanolic solution of [Ru(η6-p-cymene)(PPh3)Cl2] (0.180 mmol; 0.100 g). The mixture was kept under inert atmosphere and was stirred for 1 h and then NH4PF6 (0.300 mmol; 0.050 g) was added. The reaction mixture was concentrated under reduced pressure, until precipitation of an orange solid. The solid was filtered off, washed with water (3 * 5 mL), cold methanol (3 * 5 mL) and dried under vacuum.
  • 74
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 52490-94-5 ]
  • N-(2-furoyl)-N’-piperonylthiourea [ No CAS ]
  • C42H40N2O4PRuS(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: The acylthiourea ligand (0.190 mmol) was dissolved in 25 mL methanolicsolution of [Ru(η-6-p-cymene)(PPh3)Cl2] (0.180 mmol;0.100 g). After stirring for 0.5 h, under inert atmosphere, 25 mL ofdeaerated water was added. The mixture was kept under inert atmosphereand reflux, and was stirred for 3 h. For precipitation of a yellowsolid, NH4PF6 (0. 300 mmol; 0.050 g) was added. The solid was filteredoff, washed with water (3×5 mL) and dried under vacuum.
  • 75
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 52490-94-5 ]
  • N-(2-thiophenecarbonyl)-N’-piperonylthiourea [ No CAS ]
  • C42H41ClN2O3PRuS2(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: The precursors and acylthiourea ligands were synthesized according to previous reports [25,50,51].The acylthiourea ligand (0.190 mmol) was added to 50 mL of methanolic solution of [Ru(η6-p-cymene)(PPh3)Cl2] (0.180 mmol; 0.100 g). The mixture was kept under inert atmosphere and was stirred for 1 h and then NH4PF6 (0.300 mmol; 0.050 g) was added. The reaction mixture was concentrated under reduced pressure, until precipitation of an orange solid. The solid was filtered off, washed with water (3 * 5 mL), cold methanol (3 * 5 mL) and dried under vacuum.
  • 76
  • germanium(II) chloride dioxane [ No CAS ]
  • [ 52490-94-5 ]
  • [(η6-p-cymene)Ru(PPh3)Cl(trichlorogermyl)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% In dichloromethane; for 0.25h;Glovebox; Inert atmosphere; Schlenk technique; Dichloro(p-cymene)ruthenium(II) dimer (0.509 g, 8.31 x 10-4 mol)was measured and added to triphenylphosphine (3.268 g, 1.25 x 10-2mol) in a round bottomed flask. Dichloromethane (50 mL) was added tothis vessel, and the reaction mixture was stirred under reflux (50 C) for3 h. No colour change occurred across the duration of this reaction,remaining a transparent dark red solution throughout. The solvent wasremoved in vacuo at 40 C to a highly concentrated solution (∼8 mL). Diethyl ether (50 mL) was added to this solution, causing the product toprecipitate out of solution, and the supernatant was subsequently decantedoff. This was repeated four more times until the decanted supernatantwas colourless. A dark red crystalline material was obtained,and was allowed to air dry for 1 h before proceeding with analysis andfurther reactions. A yield of 0.748 g (1.32 x 10-3 mol, 79.2%) wasrecorded.This product, [Ru(η6-p-cymene)Cl2(PPh3)], (0.300 g, 5.28 x 10-4mol) was added to a Schlenk flask within a glovebox under an inert N2atmosphere. Germanium(II) chloride dioxane complex (1:1) (0.129 g,5.55 x 10-4 mol) was then added to this vessel, which was then sealedand placed on a Schlenk line. Dried and degassed dichloromethane(20 mL) was added to this vessel. This reaction mixture was allowed tostir for 15 min. The solution went from a transparent cabernet red to atransparent amber solution in approximately 1 min. This solvent wasthen concentrated in vacuo at 40 C to form a highly concentrated solution(∼5 mL), until the point of insipience was reached. This solutionwas allowed to rest, before decanting the supernatant off, leaving behindan orange-red semi-crystalline residue. This material was thendried in vacuo for 15 min at room temperature. Soluble in dichloromethane, sparingly soluble in chloroform anddimethyl sulfoxide. Air stable. 0.238 g of orange-red solid (63%).Melting Point: 124 C+dec.1H NMR: (300.1 MHz, CHCl3-d1, 25 C): δ= 7.66 - 7.23 (m, 15H, PPh3), 6.10 (d, 3J(H,H) = 6.1 Hz, 1H, η6-C6H4),5.68 (d, 3J(H,H)=5.9 Hz, 1H, η6-C6H4), 5.39 (d, 3J(H,H)=5.9 Hz, 1H,η6-C6H4), 4.79 - 4.77 (m, 1H, η6-C6H4), 2.70 (sept, 3J(H,H) = 6.9 Hz,1H CH(CH3)2), 1.52 (s, 3H, CH3), 1.21 (d, 3J(H,H) = 6.9 Hz, 3H, CH(CH3)2A), 1.16 (d, 3J(H,H) = 6.9 Hz, 3H, CH(CH3)2B). 13C{1H}NMR:(75.5 MHz, CHCl3-d1, 26 C, ppm): δ = 133.4 (d, xJ(C,P) = 9.9 Hz, C2,6or C3,5 PPh3), 132.6 (d, 1J(C,P) = 48.0 Hz, C1 PPh3), 129.6 (d, 4J(C,P)= 2.5 Hz, C4 PPh3), 127.3 (d, xJ(C,P) = 10.3 Hz, C2,6 or C3,5 PPh3),98.0 (s, η6-C6H4), 94.2 (d, 2J(C,P)=3.4 Hz, η6-C6H4), 92.7 (s, η6-C6H4),88.0 (s, η6-C6H4), 87.4 (s, η6-C6H4), 87.3 (s, η6-C6H4), 29.3 (s, CH(CH3)2), 21.2 (s, CH(CH3)2A), 20.7 (s, CH(CH3)2B), 15.9 (s, CH3). 31P{1H}NMR: (121.5 MHz, CHCl3-d1, 26 C): δ = 28.9 (s). 31P{1H}NMR:(121.5 MHz, DMSO-d6, 26 C, ppm): δ=32.9 (s, exchanged, 30%), 29.3(s, product, 70%). HRMS (ESI (+)) = 706.99000 (2%), 682.02768(16%), 668.99667 (100%), 641.00159 (16%), 574.10092 (6%),533.07416 [M-GeCl3]+ (calc 533.07388) (24%), 279.09349 (6%).ATR-FTIR: ν(cm-1) = 2988 (m), 2970 (m), 2901 (m, Alkyl C-HStretching), 2872 (m), 2361 (m), 2322 (m), 1977 (w), 1558 (w), 1541(w), 1506 (m, Aromatic C=H Bending), 1487 (w), 1472 (m), 1456 (m),1433 (s), 1395 (w), 1375 (m), 1339 (w), 1314 (w), 1260 (m), 1182 (w),1159 (w), 1090 (vs), 1059 (s), 1028 (s), 1001 (m), 972 (w), 924 (w),901 (w), 860 (m), 845 (w), 799 (s, Aromatic C=C Bending), 746 (vs),691 (vs), 669 (m, P-C), 631 (s), 617 (w). TGA: (C, Weight % decrease):222 - 254 (12%), 254 - 287 (4%), 287 - 373 (19%), 373 - 493 (16%).UV/Vis λmax (dichloromethane): 358.0 nm.
  • 77
  • [ 17084-13-8 ]
  • [ 52490-94-5 ]
  • [ 7732-18-5 ]
  • C28H31ClOPRu(1+)*F6P(1-) [ No CAS ]
  • 78
  • [ 52490-94-5 ]
  • [ 23593-75-1 ]
  • hexafluorophosphate salt [ No CAS ]
  • [RuCl(clotrimazole)(η6-p-cymene)(PPh3)]PF6 [ No CAS ]
  • 79
  • [ 52490-94-5 ]
  • ketoconazole [ No CAS ]
  • hexafluorophosphate salt [ No CAS ]
  • [RuCl(ketoconazole)(η6-p-cymene)(PPh3)]PF6 [ No CAS ]
  • 80
  • [ 52490-94-5 ]
  • [ 86386-73-4 ]
  • hexafluorophosphate salt [ No CAS ]
  • [RuCl(fluconazole)(η6-p-cymene)(PPh3)]PF6 [ No CAS ]
  • 81
  • [ 52490-94-5 ]
  • sodium dihydro(2-mercaptopyridyl)borate [ No CAS ]
  • C33H29BN3PRuS3 [ No CAS ]
  • C20H20B2N4RuS4 [ No CAS ]
  • 82
  • [ 52490-94-5 ]
  • Na dihydrobis(2-mercapto-benzothiazolyl)borate [ No CAS ]
  • C28H20B2N4RuS8 [ No CAS ]
  • C39H29BN3PRuS6 [ No CAS ]
  • 83
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 52490-94-5 ]
  • [ 29511-50-0 ]
  • [Ru(η6-p-cymene)(PPh3)(N’,N’-dimethyl-N’-benzoylthiourea)Cl](PF6) [ No CAS ]
  • 84
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 52490-94-5 ]
  • [ 29511-50-0 ]
  • [Ru(η6-p-cymene)(PPh3)(N’,N’-dimethyl-N’-benzoylthiourea)](PF6) [ No CAS ]
  • 85
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 52490-94-5 ]
  • [ 58328-36-2 ]
  • [Ru(η6-p-cymene)(PPh3)(N’,N’-diethyl-N’benzoylthiourea)Cl](PF6) [ No CAS ]
Same Skeleton Products
Historical Records