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CAS No. : | 52462-29-0 | MDL No. : | MFCD00064793 |
Formula : | C20H28Cl4Ru2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LAXRNWSASWOFOT-UHFFFAOYSA-J |
M.W : | 612.39 | Pubchem ID : | 10908223 |
Synonyms : |
|
Num. heavy atoms : | 26 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 104.97 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.26 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 5.25 |
Log Po/w (WLOGP) : | -6.8 |
Log Po/w (MLOGP) : | 6.33 |
Log Po/w (SILICOS-IT) : | 6.34 |
Consensus Log Po/w : | 2.23 |
Lipinski : | 2.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 4.0 |
Bioavailability Score : | 0.17 |
Log S (ESOL) : | -6.76 |
Solubility : | 0.000104 mg/ml ; 0.000000173 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -5.0 |
Solubility : | 0.00606 mg/ml ; 0.00001 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -8.3 |
Solubility : | 0.00000301 mg/ml ; 0.000000005 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.85 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P273-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H412 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere; | General procedure: A 50-mL round-bottom flask was charged with [Ru(p-cymene)Cl2]2 (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, 86percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | 0.3g (0.49mmol) of [Ru (p-cymene)2CI2]2 are added to 60 ml of DMF under nitrogen inert atmosphere at atmospheric pressure, to this solution 0,4g (0,98 mmol) of 4,4'-dinonyl-2,2'-pyridyl (dnbpy) are added and the resultant mixture is heated at 60C for 2h. Successively 0,24 g (0,98 mmol) of 4,4'-dicarboxy-2,2'-pyridyl (Hdcbpy2) are added and the reaction mixture is heated under reflux (160C) for 4h. 0.24g (0.98mmol) of Hdcbpy2 and 0.157g (3.9mmol) of NaOH are dissolved in 3ml of water and then added to reaction mixture then refluxed over further 2h.The reaction mixture is hot filtered and the solvent is removed under vacuum evaporation. Obtained solid is dissolved in basic NaOH solution and the product precipitated at pH = 2 by addition of aqueous HPF6 solution. The dissolution and precipitation procedures are repeated two times, the precipitate is washed with aqueous HPF6 solution and finally with ethyl ether. Yield 60%.The resulting product, without further purifications, is characterized by cyclic voltammetry (figure 20) and JV plot (figure 21) .Particularly, figure 20 shows cyclic voltammogramm of [cis-Ru (HDCBPy2)2(dnbpy)]2+ product obtained according to the conventional thermal synthesis under the following experimental conditions: electrolytic solution: L1CIO4 0.1N in acetonitrile, working electrode: glassy carbon, reference electrode: SCE.Figure 2 vshows DSSC JV plot for [cis-Ru (HDCBPy2)2 (dnbpy)]2+ dye obtained according to known art by thermal synthesis under following simulated experimental irradiation conditions (AM 1.5 75mW cm"2): Mediator/electrolyte: Co(DTB)3 (OTf)2 0.15M, Fe(DMB)3 (PF6)2 0,015M, Li (OTf) 0.5M in acetonitrile. (DTB = 4,4'-dimethyl-2,2'-bipyridyl, DMB = 4,4'- diterbutyl-2,2'-bipyridyl, OTf = p-toluenesulphonate). Cathode: potentiostatically (15s) electrocoated PEDOT (polyethylene dioxide thiophene) FTO. Transparent TiO2. Photovoltaic parameters corresponding to Figure 21 (Jsc, Voc, FF, e eta) are respectively: 2.56 mA cm"2 369 mV, 0.49 and 0.66%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.3% | In ethanol; at 50℃; for 3h; | 6-Fluoropyridine-2-carboxylic acid (HL3) (28 mg, 0.2 mmol) in ethanol (3 ml) was added to a solution of [Ru(eta6-p-cymene)Cl2]2 (61 mg, 0.1 mmol) in ethanol (5 ml) at 50 °C. The yellow solution was stirred for 3 h. The solvent was removed by one half under reduced pressure and the concentrated solution was placed in a fridge. Next day orange product was filtered off, washed with EtOH (5 ml) and dried in air. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.8% | In ethanol; at 20℃; for 2h; | To a warm solution of [Ru(eta6-p-cymene)Cl2]2 (61 mg, 0.1 mmol) in ethanol (5 ml) <strong>[6624-49-3]isoquinoline-3-carboxylic acid</strong> (HL7) (38 mg,0.2 mmol) in ethanol (3 ml) was added. The mixture was stirred at room temperature for 2 h. The yellow product was filtered off, washed with EtOH (5 ml) and dried in air. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To Dichloro-p-cymene ruthenium dimer (0.050 g, 0.090 mmol, 1.00 equiv.) dissolved in dry, degassed DMF (20 mL), under argon, and shielded from light was added donor ligand dnbpy 10 (0.073 g, 0.180 mmol, 2.00 equiv.). The mixture was stirred at 75 C for 5 h, cooled to room temperature, and stirred for 12 h. After adding dpbpy 7 (0.150 g, 0.360 mmol, 4 equiv.) the reaction mixture was refluxed for 4 h resulting in a dark-red solution. The solvent was removed in vacuo and the crude product purified by size exclusion chromatography on a Sephadex LH-20 column using water. Aqueous HCl (6 M, 25 mL) was added to the main fraction and the resulting solution was refluxed for 15 h. The black solution was purified by size exclusion chromatography on a Sephadex LH-20 yielding 4 (40.0 mg, 0.045 mmol, 28.0 %). | ||
In methanol; | General procedure: All compounds were synthesized using a similar procedure.[(h6-p-cymene)RuCl2]2 (e.g. 150 mg, 0.245 mmol) was dissolved in25e30 ml methanol and a calculated stoichiometric amount ofligand was added neat. After stirring for a minimum of 0.5 h (oruntil all ligand has dissolved) at ambient temperature the solventwas removed under vacuum on a rotary evaporator. The residuewas washed and stirred repeatedly with Et2O and each Et2O washphase was carefully decanted from the readily settling and insolubleproduct. The final product was dried under vacuum at RT e40 C; in all cases yields were 90%. Complexes Characterisationdata for individual complexes are reported in the following. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In ethanol; for 4h;Reflux; | Example 2 Synthesis of Ruthenium Complex K23 (0113) The complex K23 was synthesized by refluxing a mixture of 4,4?-dinonyl-2,2?-bipyridine (150 mg, 0.37 mmol) and dichloro(p-cymene)ruthenium(II) dimer (113 mg, 0.18 mmol) in argon degassed absolute ethanol (40 mL) for 4 h. Evaporation of the solvent leaded to dichloro(p-cymene)-4,4?-dinonyl-2,2?-bipyridine-ruthenium(II) complex as a brow-yellow oil in a quantitative yield. This intermediate complex was used without further purification for reacting with 4,4?-dicarboxy(phenylethenyl)-2,2?-bipyridine (0.36 mmol) in dry and argon degassed DMF (30 mL). The mixture was heated at 150 C. for 4 h and to the resulting dark purple solution was added NH4NCS (408 mg, 5.4 mmol) and the mixture heated at 150 C. for 4 h more. After evaporation of the DMF, the resulting purple residue was suspended in water (200 mL) and sonicated for 5 min. The pH was adjusted to 3 with HNO3 (0.02 M) and the mixture was let stand in the fridge overnight. The crude complex was dissolved in methanol containing two equivalents of tetrabutylammonium hydroxide. The concentrated solution was filtered through a sintered glass crucible and charged onto a LH-20 Sephadex column, which was prepared in methanol. The adsorbed complex was eluted using methanol as an eluent. The main band was collected and the solution pH was lowered to 3 using 0.02 M HNO3 acid. The precipitated complex was collected on a glass fit and air-dried. Yield 60 mg, 32%. The analytical and spectroscopic data are consistent with the structures shown in FIG. 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | General procedure: [RuCl2(p-cymene)]2 (0.12 g, 0.20 mmol), glycine (0.03 g,0.40 mmol) and potassium tert-butoxide (0.05 g, 0.40 mmol) wereadded to dry methanol (40 mL), and the resulting mixture wasrefluxed for 30 min under argon atmosphere. AgNO3 (0.14 g,0.80 mmol) and dcmb (0.23 g, 0.85 mmol) were then added andthe reaction mixture was refluxed for additional 14 h in the dark.The reaction mixture was cooled to room temperature and filteredthrough a fine porosity frit to remove precipitated AgCl andexceeding dcmb. The filtrate was evaporated to dryness, and theresidue was recrystallized from a mixture of chloroform and hexane(v/v = 2:1), and dried in a vacuum to afford complex 3 as deepblue powder in a yield of 0.16 g (50percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | [RuCl2(p-cymene)]2 (0.12 g, 0.20 mmol) and 1,10-phenanthrolinemonohydrate (0.08 g, 0.40 mmol) were added to dry methanol(40 mL), and the resulting mixture was refluxed for 4 h under argonatmosphere. AgNO3 (0.14 g, 0.80 mmol) and dcmb (0.23 g,0.85 mmol) were then added and the reaction mixture was refluxedfor additional 14 h in the dark. The reaction mixture was cooled toroom temperature, concentrated to ~5 mL and filtered through afine porosity frit to remove precipitated AgCl and exceeding dcmb.A 2 mL methanol solution of NaClO4H2O (0.17 g, 1.20 mmol) wasadded into the filtrate, and the mixture was stirred vigorously atroomtemperature for 1 hto complete the anion exchange. The resultantsolid was collected by filtration through a medium porosity frit,washed with diethyl ether (3 10 mL), and dried in vacuo to affordcomplex 1 as red powder in a yield of 0.34 g (70percent). 1H NMR (DMSOd6,500 MHz, ppm) delta: 9.39 (d, J = 16.1 Hz, 4H), 8.86 (d, J = 8.2 Hz, 2H),8.42 (s, 2H), 8.16 (d, J = 5.0 Hz, 2H), 8.12 (d, J = 5.8 Hz, 2H), 7.91?7.87(m, 4H), 7.79 (d, J = 5.8 Hz, 2H), 7.75 (d, J = 5.7 Hz, 2H), 3.98 (d,J = 26.8 Hz, 12H). Positive ESI-MS in methanol (m/z): 413.5 [M]2+/2.Anal. Calc. for C40H32Cl2N6O16Ru: C, 46.89; H, 3.15; N, 8.20. Found:C, 46.68; H, 3.26; N, 8.01percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | [RuCl2(p-cymene)]2 (0.12 g, 0.20 mmol), glycine (0.03 g,0.40 mmol) and potassium tert-butoxide (0.05 g, 0.40 mmol) wereadded to dry methanol (40 mL), and the resulting mixture wasrefluxed for 30 min under argon atmosphere. AgNO3 (0.14 g,0.80 mmol) and dcmb (0.23 g, 0.85 mmol) were then added andthe reaction mixture was refluxed for additional 14 h in the dark.The reaction mixture was cooled to room temperature and filteredthrough a fine porosity frit to remove precipitated AgCl andexceeding dcmb. The filtrate was evaporated to dryness, and theresidue was recrystallized from a mixture of chloroform and hexane(v/v = 2:1), and dried in a vacuum to afford complex 3 as deepblue powder in a yield of 0.16 g (50percent). 1H NMR (DMSO-d6,500 MHz, ppm) delta: 9.66 (d, J = 5.4 Hz, 1H), 9.35 (s, 1H), 9.26 (s,1H), 9.15?9.10 (m, 2H), 8.38 (d, J = 5.3 Hz, 1H), 8.26 (d, J = 5.7 Hz,1H), 8.08 (d, J = 5.8 Hz, 1H), 7.99 (d, J = 5.6 Hz, 1H), 7.68 (d,J = 5.7 Hz, 1H), 7.63 (d, J = 4.7 Hz, 1H), 7.60 (d, J = 5.7 Hz, 1H),5.08 (s, 1H), 4.43 (s, 1H), 4.08 (d, J = 9.9 Hz, 6H), 3.98 (d,J = 13.1 Hz, 2H), 3.93 (s, 6H). Positive ESI-MS in methanol (m/z):720.3 [M]+. Anal. Calc. for C30H28N6O13Ru: C, 46.10; H, 3.61; N,10.75. Found: C, 46.31; H, 3.78; N, 10.56percent. Single crystals of complex3 suitable for X-ray diffraction measurement were grownfrom methanol by slow evaporation in air at room temperaturefor one week. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | General procedure: [RuCl2(p-cymene)]2 (0.12 g, 0.20 mmol), glycine (0.03 g,0.40 mmol) and potassium tert-butoxide (0.05 g, 0.40 mmol) wereadded to dry methanol (40 mL), and the resulting mixture wasrefluxed for 30 min under argon atmosphere. AgNO3 (0.14 g,0.80 mmol) and dcmb (0.23 g, 0.85 mmol) were then added andthe reaction mixture was refluxed for additional 14 h in the dark.The reaction mixture was cooled to room temperature and filteredthrough a fine porosity frit to remove precipitated AgCl andexceeding dcmb. The filtrate was evaporated to dryness, and theresidue was recrystallized from a mixture of chloroform and hexane(v/v = 2:1), and dried in a vacuum to afford complex 3 as deepblue powder in a yield of 0.16 g (50percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | General procedure: [RuCl2(p-cymene)]2 (0.12 g, 0.20 mmol), glycine (0.03 g,0.40 mmol) and potassium tert-butoxide (0.05 g, 0.40 mmol) wereadded to dry methanol (40 mL), and the resulting mixture wasrefluxed for 30 min under argon atmosphere. AgNO3 (0.14 g,0.80 mmol) and dcmb (0.23 g, 0.85 mmol) were then added andthe reaction mixture was refluxed for additional 14 h in the dark.The reaction mixture was cooled to room temperature and filteredthrough a fine porosity frit to remove precipitated AgCl andexceeding dcmb. The filtrate was evaporated to dryness, and theresidue was recrystallized from a mixture of chloroform and hexane(v/v = 2:1), and dried in a vacuum to afford complex 3 as deepblue powder in a yield of 0.16 g (50percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | General procedure: [RuCl2(p-cymene)]2 (0.12 g, 0.20 mmol) and 1,10-phenanthrolinemonohydrate (0.08 g, 0.40 mmol) were added to dry methanol(40 mL), and the resulting mixture was refluxed for 4 h under argonatmosphere. AgNO3 (0.14 g, 0.80 mmol) and dcmb (0.23 g,0.85 mmol) were then added and the reaction mixture was refluxedfor additional 14 h in the dark. The reaction mixture was cooled toroom temperature, concentrated to ~5 mL and filtered through afine porosity frit to remove precipitated AgCl and exceeding dcmb.A 2 mL methanol solution of NaClO4H2O (0.17 g, 1.20 mmol) wasadded into the filtrate, and the mixture was stirred vigorously atroomtemperature for 1 hto complete the anion exchange. The resultantsolid was collected by filtration through a medium porosity frit,washed with diethyl ether (3 10 mL), and dried in vacuo to affordcomplex 1 as red powder in a yield of 0.34 g (70percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Ruthenium (II) p-cymene Dimer (3) (10mg, 0.016 mmol) was dissolved in 5 ml ofmethanol in 25 mL RB flask placed on a magnetic stirrer and stirred for 30 min.Subsequently, Pyridine-2-carboxaldehyde (1)& <strong>[6945-68-2]2-amino-5-bromo-3-nitropyridine</strong> (2q) (2:2 equivalent with respect to the ruthenium dimer) was addedto reaction mixture and then stirred continuously for 24 h at room temperature. Ammonium hexafluorophosphate (1:1) was added, colourchange was observed from deep yellow to deep red. Then we performed the TLC in1% methanol in ethyl acetate. After completion of the reaction we haveevaporated the methanol by using rotator evaporator. The crude product was recrystallizedfrom 5% methanol in diethyl ether; fine brown crystal was obtained with 90%yield. Spectral DataYield: 90 %, Mp: 146-148C, Rf (1% MeOH in EthylAcetate):0.26. 1H NMR (DMSO-d6, 400 MHz): delta 1.04-1.18 (m, 6H, Cymene CH3),1.12(s, 3H, Cymene CH3), 2.69-2.80 (m, 1H, J = 12 Hz, Cymene CH), 5.60-5.63 (m, 1H, Cymene ArH), 5.75-5.82 (m,2H, Cymene ArH), 5.91-5.95 (m, 1H, Cymene ArH), 7.71-7.76 (m, 1H, ArH), 7.89 (brs, 1H, ArH),7.98-8.04 (m, 1H, ArH), 8.46-8.48 (m, 2H, ArH), 8.69-8.74 (m, 1H, ArH), 9.23(brs, 1H, imine CH); 13C NMR (DMSO-d6, 400MHz): delta 21.4 (CH3), 21.4 (CH3), 21.8 (CH3),30.4 (CH), 80.0, 81.0, 82.4, 82.5, 101.0, 103.6, 124.2, 125.2, 127.1, 128.1,136.2, 139.6, 141.4, 141.6, 152.4, 153.7, 156.4, 170.5 (-C=N); 31P NMR (DMSO-d6, 400 MHz): delta -157.30 (m, PF6);19F NMR (DMSO-d6, 400 MHz): delta -71.00 (6F, PF6);ESI-MS (MeOH): m/z: 545 [M]+, 547 [M+2]+; HRMS(ESI): m/z calcd for C21H21N4BrClRu+:544.9682 [M]+; found: 544.9686 [M]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | General procedure: 0.851 g of ruthenium (III) chloride hydrate and 40 ml of N-methylpyrrolidone were added to the first reactor(4,4'-dinonyl-2,2'bipyridine) was added thereto while stirring and the mixture was stirred for 0.5 hour. In the second reactor, ligand 2(2,2'-bipyridine-4,4'-dicarboxylic acid) and 60 ml of N-methylpyrrolidone were placed and maintained at 140 to 150 C. The mixed solution of the first reactor was added to the second reactor,Stirring was continued for 1.5 hours while maintaining the temperature at 140 to 150 C, and ammonium thiocyanate5.16 g was added and stirred for 1 hour and then the reactor was cooled. The reaction mixture was poured into distilled water to precipitate a solid. The solid was dissolved in methanol40 ml and NaOH were used to maintain the pH of 10 to 11, After purification by column using Sephadex resin,the solution was adjusted to pH 4.8 with nitric acid to give a solid to give the desired compound. Instead of ruthenium (III) chloride hydrate, [RuCl2 (p-cymene)] 2 Except that the complex compound was used, a heteroleptic ruthenium complex dye was synthesized in the same manner. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium acetate; In dichloromethane; at 20℃; for 20h;Inert atmosphere; Schlenk technique; | Dichloromethane (10 mL) was added to dichloro(pcymene)ruthenium(II) dimer (0.16 mmol) in a round bottom flask. To this solution were added, L6 (0.33 mmol) followed by potassium acetate(0.38 mmol). The reaction mixturewas stirred at room temperature for 20 h. Then the solvent was evaporated and the residue leftbehind was dissolved in dichloromethane and the mixture wasfiltered. The filtratewas then added to large volume of diethyl etherresulting in a precipitate which was filtered and washed withdiethyl ether and dried. (90 mg, 60percent yield) 1H NMR (CDCl3,400 MHz): delta 0.80 (3H, d, J 6.8 Hz, isopropyl), 0.94 (3H, d,J 6.8 Hz, isopropyl), 2.08 (3H, s, methyl), 2.31 (1H, m, isopropyl),4.10 (3H, s, N-methyl), 5.14 (1H, d, J 5.9 Hz, cymene), 5.36 (1H, d,J 5.9 Hz cymene), 5.70 (1H, d, J 5.9 Hz, cymene), 5.84 (1H, d,J 5.9 Hz, cymene) 7.07 (1H, m, ArH), 7.21 (1H, m, ArH), 7.40 (3H, m,ArH), 7.80 (1H, m, ArH), 7.9 (1H, d, J 7.6 Hz, ArH), 8.33 (1H, d,J 7.6 Hz, ArH). 13C NMR (CDCl3, 100 MHz): delta 19.42, 22.36, 23.08,31.35, 32.41, 81.77, 82.17, 89.26, 89.77, 99.43, 101.55, 110.27, 117.49,122.89, 123.48, 123.61, 124.80,129.36, 134.62, 136.74, 140.99, 141.84,158.86, 183.66. Elemental analysis for C24H25Cl1N2Ru, calcd. (percent) C,60.31; H, 5.27; N, 5.86. Found: C, 60.16; H, 5.14; N, 5.90. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40.32% | In toluene; at 100℃; for 3h; | 2.2.2 Synthesis of [Ru(eta6-p-cymene)(N-PrIm)Cl2] (2) The [Ru(eta6-p-cymene)(N-PrIm)Cl2] was synthesized following the literature method of Vock et al [10] . To a suspension of [Ru-(eta6-p-cymene)Cl2]2 (0.199?g, 0.326?mmol) in toluene (30?mL), <strong>[35203-44-2]N-Propylimidazole</strong> (0.0756?mL, 0.652?mmol) was added at room temperature. The resulting mixture was heated and refluxed for 3?h. After, the mixture was cooled, and the precipitate was filtered. Crystals suitable for X-ray structure analysis were obtained from toluene filtrate (109.5?mg, yield: 40.32percent). Melting point?=?198?°C. Anal. Cal. for C16H24N2Cl2Ru (Mw?=?416.34) C: 46.16, H: 5.81, N: 6.73; found: C: 46.66, H: 5.69, N: 6.58percent. 1HNMR (200?MHz, CDCl3): delta(ppm) 0.93 (t, 3H, 3"-H3), 1.28 (d, 6H, 1-CH(CH3)2), 1.70-1.89 (m, 2H, 2"-H2), 2.19 (s, 3H, 4-CH3), 2.97 (sept, 1H, 1-CH(CH3)2), 3.85 (t, 2H, 1"-H2), 5.24 (d, 2H, 2-H, 6-H), 5.44 (d, 2H, 3-H, 5-H), 6.88 (t, 1H, 4'-H), 7.32 (t, 1H, 5'-H), 7.90 (t, 1H, 2'-H). 13CNMR (50?MHz, CDCl3): delta(ppm) 11.02 (C-3"), 18.51 (4-CH3), 22.28 (1-CH(CH3)2), 23.92 (1-CH(CH3)2), 30.71 (C-2"), 49.89 (C-1"), 81.39 (C-2, C-6), 82.67 (C-3, C-5), 97.36 (C-4), 102.54 (C-1), 119.36 (C-4'), 132.16 (C-5'), 139.78 (C-2'). IR (KBr, pellet): nu (cm-1) 3143, 3110, 3044 (nu=CH), 2958, 2931, 2874 (nuCH), 1618 (nuC=N), 1533, 1520, 1498 (nuC=C). UV-Vis (H2O, C?=?10-4 M): lambdamax/nm (epsilon/L mol-1 cm-1): 254 (3005.21), 307 (1865.98) and 393 (1123.65). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.72 g | Step A)0.31 g of p-cymene dichloride dimer,0.41g<strong>[142646-58-0]4,4'-dinonyl-2,2'-bipyridine</strong>And 50 mL of N,N-dimethylformamide was placed in a three-necked flask, and the solution was stirred for 15 minutes in an atmosphere of light and Ar gas, and then heated to 80.C, reaction for 4 hours. Then cooled to room temperature;Step B)0.30 g was added to the three-necked flask after the reaction in the step A)2,2'-bipyridyl-4,4'-dicarboxylic acid diethyl ester,The solution was stirred for 15 minutes in an atmosphere of light and Ar gas, and then heated to 130 C for 5 hours.Then cooled to room temperature;Step C)0.97 g of NH4NCS was added to the three-necked flask after the reaction in the step B), in the dark and Ar gas atmosphere,After the solution was stirred for 15 minutes, it was heated to 120 C and reacted for 4 hours. After cooling to room temperature,The N,N-dimethylformamide was evaporated to dryness on a rotary evaporator. Add 150 mL of water to the remaining liquid.It was extracted three times with 150 mL of chloroform, and the obtained chloroform solution was washed three times with water, and then dried over anhydrous magnesium sulfate.After filtering, the filtrate is distilled off with a rotary evaporator, and the obtained solid is dried.Obtaining 1.08 g of the esterified product of Z907, the purity is 81.9%;Step D)1.08 g of the esterified product of Z991 obtained in step C) was dissolved in ethyl acetate.The mixture was purified by silica gel column chromatography using a mixture of ethyl acetate and n-hexane.The collected product solution, distilled off the solvent, and dried.Obtaining 0.72 g of the esterified product of Z907, the purity is 96.2%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.93 g | Step A)0.31 g of p-cymene dichloride dimer,0.82 g of 4,4'-bis(5-octylthiophene[3,2b]thiophen-2-yl)-2,2'-bipyridine and 50 mLN,N-dimethylformamide was placed in a three-necked flask in an atmosphere of light and Ar gas.After the solution was stirred for 15 minutes, it was heated to 70 ° C and reacted for 5 hours. Then cooled to room temperature;Step B)To the three-necked flask after the reaction of the step A), 0.27 g of dimethyl 2,2'-bipyridyl-4,4'-dicarboxylate was added.The solution was stirred for 15 minutes in an atmosphere of light and Ar gas, and then heated to 130 ° C for 4 hours.Then cooled to room temperature;Step C)0.97 g of NH4NCS was added to the three-necked flask after the reaction in the step B), in the dark and Ar gas atmosphere,After the solution was stirred for 15 minutes, it was heated to 120 ° C and reacted for 4 hours. After cooling to room temperature,The N,N-dimethylformamide was evaporated to dryness on a rotary evaporator. Add 150 mL of water to the remaining liquid.Extracted three times with 150 mL of chloroform, and the obtained chloroform solution was washed three times with water.It was then dried over anhydrous magnesium sulfate. After filtration, the filtrate was evaporated to dryness on a rotary evaporator.After drying the obtained solid, 1.22 g of the esterified product of C104 was obtained, and the purity was 81.2percent;Step D)1.22 g of the esterified product of C104 obtained in step C) was dissolved in ethyl acetate.The mixture was purified by silica gel column chromatography using a mixture of ethyl acetate and n-hexane of 18:1.The collected product solution, distilled off the solvent, and dried.Obtaining 0.93 g of the esterified product of C106, the purity is 96.2percent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.85 g | Step A)0.31 g of p-cymene dichloride dimer,0.55 g of 4,4'-bis(5-hexylthiothiophen-2-yl)-2,2'-bipyridine and 50 mLN,N-dimethylformamide was placed in a three-necked flask in an atmosphere of light and Ar gas.After the solution was stirred for 15 minutes, it was heated to 70 ° C and reacted for 5 hours. Then cooled to room temperature;Step B)To the three-necked flask after the reaction of the step A), 0.27 g of dimethyl 2,2'-bipyridyl-4,4'-dicarboxylate was added.The solution was stirred for 15 minutes in an atmosphere of light and Ar gas, and then heated to 130 ° C for 4 hours.Then cooled to room temperature;Step C)0.97 g of NH4NCS was added to the three-necked flask after the reaction in the step B), in the dark and Ar gas atmosphere,After the solution was stirred for 15 minutes, it was heated to 120 ° C and reacted for 4 hours. After cooling to room temperature,The N,N-dimethylformamide was evaporated to dryness on a rotary evaporator. Add 150 mL of water to the remaining liquid.Extracted three times with 150 mL of chloroform, and the obtained chloroform solution was washed three times with water.It was then dried over anhydrous magnesium sulfate. After filtration, the filtrate was evaporated to dryness on a rotary evaporator.After drying the obtained solid, 1.10 g of the esterified product of C106 is obtained, and the purity is 80.5percent;Step D)1.10 g of the esterified product of C106 obtained in step C) was dissolved in ethyl acetate.The mixture was purified by silica gel column chromatography using a mixture of ethyl acetate and n-hexane of 18:1.The collected product solution, distilled off the solvent, and dried.Obtaining 0.85 g of the esterified product of C106, the purity is 96.3percent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.82 g | Step A)0.31 g of p-cymene dichloride dimer,0.56 g of 4,4'-bis(4-hexyloxystyryl)-2,2'-bipyridine and 50 mLN,N-dimethylformamide was placed in a three-necked flask in an atmosphere of light and Ar gas.After the solution was stirred for 15 minutes, it was heated to 80 C and reacted for 4 hours. Then cooled to room temperature;Step B)To the three-necked flask after the reaction of the step A), 0.27 g of dimethyl 2,2'-bipyridyl-4,4'-dicarboxylate was added.The solution was stirred for 15 minutes in an atmosphere of light and Ar gas, and then heated to 130 C for 4 hours.Then cooled to room temperature;Step C)0.97 g of NH4NCS was added to the three-necked flask after the reaction in the step B), in the dark and Ar gas atmosphere,After the solution was stirred for 15 minutes, it was heated to 120 C and reacted for 4 hours.After cooling to room temperature, the N,N-dimethylformamide was evaporated to dryness using a rotary evaporator.150 mL of water was added to the remaining liquid, and extracted with 150 mL of chloroform for 3 times.The obtained chloroform solution was washed three times with water and then dried over anhydrous magnesium sulfate.After filtering, the filtrate is distilled off with a rotary evaporator, and the obtained solid is dried.Obtaining 1.12 g of the esterified product of K19, the purity is 81.9%;Step D)1.12 g of the esterified product of K19 obtained in step C) was dissolved in ethyl acetate.The mixture was purified by silica gel column chromatography using a mixture of ethyl acetate and n-hexane of 18:1.The collected product solution, distilled off the solvent, and dried.Obtaining 0.82 g of the esterified product of K19, the purity is 96.1%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.84 g | Step A)0.31 g of p-cymene dichloride dimer,0.51 g of 4,4'-bis(4-tert-butoxystyryl)-2,2'-bipyridine and 50 mLN,N-dimethylformamide was placed in a three-necked flask in an atmosphere of light and Ar gas.After the solution was stirred for 15 minutes, it was heated to 80 ° C and reacted for 4 hours. Then cooled to room temperature;Step B)To the three-necked flask after the reaction of the step A), 0.27 g of dimethyl 2,2'-bipyridyl-4,4'-dicarboxylate was added.The solution was stirred for 15 minutes in an atmosphere of light and Ar gas, and then heated to 130 ° C for 4 hours.Then cooled to room temperature;Step C)0.97 g of NH4NCS was added to the three-necked flask after the reaction in the step B), in the dark and Ar gas atmosphere,After the solution was stirred for 15 minutes, it was heated to 120 ° C and reacted for 4 hours.After cooling to room temperature, the N,N-dimethylformamide was evaporated to dryness using a rotary evaporator.150 mL of water was added to the remaining liquid, and extracted with 150 mL of chloroform for 3 times.The obtained chloroform solution was washed three times with water and then dried over anhydrous magnesium sulfate.After filtering, the filtrate is distilled off with a rotary evaporator, and the obtained solid is dried.Obtaining 1.13 g of the esterified product of K77, the purity is 81.7percent;Step D)1.13 g of the esterified product of K77 obtained in step C) was dissolved in ethyl acetate.The mixture was purified by silica gel column chromatography using a mixture of ethyl acetate and n-hexane.The collected product solution, distilled off the solvent, and dried.Obtaining 0.84 g of the esterified product of K77, the purity is 96.1percent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.9 g | Step A)0.31 g of p-cymene dichloride dimer,0.73g 2,2'-bipyridyl-4,4'-dicarboxylic acid)-(4,4'-bis(5-(5-hexylthiothiophen-2-yl)thiophen-2-yl)-2 , 2'-bipyridineAnd 50 mL of N,N-dimethylformamide in a three-necked flask,The solution was stirred for 15 minutes in an atmosphere of light and Ar gas, and then heated to 80 ° C for 4 hours.Then cooled to room temperature;Step B)To the three-necked flask after the reaction of the step A), 0.27 g of dimethyl 2,2'-bipyridyl-4,4'-dicarboxylate was added.The solution was stirred for 15 minutes in an atmosphere of light and Ar gas, and then heated to 130 ° C for 4 hours.Then cooled to room temperature;Step C)0.97 g of NH4NCS was added to the three-necked flask after the reaction in the step B), in the dark and Ar gas atmosphere,After the solution was stirred for 15 minutes, it was heated to 120 ° C and reacted for 4 hours.After cooling to room temperature, the N,N-dimethylformamide was evaporated to dryness using a rotary evaporator.150 mL of water was added to the remaining liquid, and extracted with 150 mL of chloroform for 3 times.The obtained chloroform solution was washed three times with water and then dried over anhydrous magnesium sulfate.After filtering, the filtrate is distilled off with a rotary evaporator, and the obtained solid is dried.Obtaining 1.21 g of the esterified product of CYC-B11 with a purity of 81.6percent;Step D)2.21 g of the esterified product of CYC-B11 obtained in step C) was dissolved in ethyl acetate.It was purified by silica gel column chromatography using a 20:1 mixture of ethyl acetate and n-hexane.The collected product solution, distilled off the solvent, and dried.Obtaining 0.90 g of the esterified product of CYC-B11 with a purity of 96.0percent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.78 g | Step A)0.31 g of p-cymene dichloride dimer,0.72 g of 4,4'-bis(5-(5-octylthiophen-2-yl)thiophen-2-yl)-2,2'-bipyridine and 50 mLN,N-dimethylformamide was placed in a three-necked flask in an atmosphere of light and Ar gas.After the solution was stirred for 15 minutes, it was heated to 90 C and reacted for 4 hours. It was then cooled to room temperature.Step B)To the three-necked flask after the reaction of the step A), 0.27 g of dimethyl 2,2'-bipyridyl-4,4'-dicarboxylate was added.The solution was stirred for 15 minutes in an atmosphere of light and Ar gas, and then heated to 100 C for 3 hours.It was then cooled to room temperature.Step C)0.97 g of NH4NCS was added to the three-necked flask after the reaction in the step B), in the dark and Ar gas atmosphere,After the solution was stirred for 15 minutes, it was heated to 120 C and reacted for 4 hours. After cooling to room temperature,The N,N-dimethylformamide was evaporated to dryness on a rotary evaporator. Add 150 mL of water to the remaining liquid.It was extracted three times with 150 mL of chloroform, and the obtained chloroform solution was washed three times with water, and then dried over anhydrous magnesium sulfate.After filtering, the filtrate is distilled off with a rotary evaporator, and the obtained solid is dried.The esterified product of Z991 was obtained in 1.15 g, and the purity was 79.5%. Step D)1.15 g of the esterified product of Z991 obtained in step C) was dissolved in ethyl acetate.It was purified by silica gel column chromatography using a 20:1 mixture of ethyl acetate and n-hexane.The collected product solution, distilled off the solvent, and dried.The esterified product of Z991 was obtained in an amount of 0.78 g, and the purity was 93.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Among them, "·" represents a boron hydrogen bond B-H. n-BuLi (1.6 M) in n-hexane solution (1.00 mL, 1.6 mmol) was slowly added dropwise to a solution of the ortho-carborane o-C2B10H10 (92.0 mg, 0.64 mmol) in tetrahydrofuran at -78 C. After stirring at this temperature for 30 minutes, the mixture was slowly warmed to room temperature and the reaction was continued for 1 hour, then bromobenzimidazole (126.7 mg, 0.64 mmol) was added, and the reaction was continued at room temperature for 6 hours.Then, the binuclear ruthenium compound [(p-cymene)RuCl2]2 (256.0 mg, 0.32 mmol) was added to the reaction system for further reaction for 3 hours.After the reaction was completed, the mixture was allowed to stand for filtration, and the solvent was evaporated under reduced pressure.The obtained crude product was subjected to column chromatography (petroleum ether / tetrahydrofuran = 6:1)The orange-red target product ruthenium (II) complex Ru (254.4 mg, yield 75%) was obtained. |
Tags: 52462-29-0 synthesis path| 52462-29-0 SDS| 52462-29-0 COA| 52462-29-0 purity| 52462-29-0 application| 52462-29-0 NMR| 52462-29-0 COA| 52462-29-0 structure
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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