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CAS No. : | 1762-42-1 | MDL No. : | MFCD06204732 |
Formula : | C16H16N2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CTXJVXIVHPUFIP-UHFFFAOYSA-N |
M.W : | 300.31 | Pubchem ID : | 12088573 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | 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 |
---|---|---|
91% | With sodium tetrahydroborate In ethanol for 3 h; Reflux | Sodium borohydride (1.87g, 49mmol) was added to a suspension of diethyl [2,2'-bipyridine]-4,4'-dicarboxylate 7 (567mg, 1.89mmol) dissolved in absolute ethanol (34mL). The solution was refluxed for 3h. After cooling to room temperature, a saturated ammonium chloride solution (24mL/g of NH4Cl) was added to decompose the excess of sodium borohydride. Ethanol was evaporated under vacuum and the resulting solid was dissolved in a minimum of water using ultrasonic bath. The solution was extracted with ethyl acetate (5×34mL), dried on sodium sulfate and concentrated under vacuum to give a white powder. Yield: 91percent, |
89% | With sodium tetrahydroborate In ethanol for 3 h; Reflux | to a suspension of the diester 4 ( 10.0 g, 33.3 mmol) in 300 ml of absolute ethanol was added sodium borohydride (25.19 g, 665.9 mmol) in one portion. The mixture was refluxed for 3 h and cooled to RT, and excess borohydride was decomposed by the dropwise addition saturated ammonium chloride solution (300 ml). Ethanol was removed under vacuum and the precipitated solid was filtered and the solid was dissolved in ethyl acetate (400 ml), washed with water ( 100 ml), dried over anhy. Na2S04and the solvent was removed under vacuum to yield the diol [2,2'-bipyridine]-4,4'-diyldimethanol 5 as awhite powder (5.9 g, 82percent). |
88% | With sodium tetrahydroborate In ethanol at 90℃; for 3 h; | Ligand 2(1.02 g, 3.40 mmol) was suspended in 200 proof ethanol (67 mL).Sodium borohydride (2.80 g, 74.0 mmol) was added and the suspension was refluxed at 90 C for 3 h. After cooling, saturated aqueous ammonium chloride (75 mL) was added and ethanol was removed in vacuo. Water was added until all white solid was dissolved.The aqueous layer was extracted with ethyl acetate (450 mL) and the combined organic layers were dried over anhydrous Na2SO4. The solvent was removed in vacuo to yielda white solid |
75% | With sodium tetrahydroborate In ethanol for 3 h; Reflux | To a suspension of compound 4 (6.0 g, 22.0 mmol) in 200 ml of absolute ethanol was added 16.4 g (0.434 mol) of sodium borohydride. The mixture was refluxed for 3 h and cooled to room temperature, and then 200 mL of an ammonium chloride saturated water solution was added to decompose the excess borohydride. The reaction mixture was evaporated to removed the ethanol, and a minimal amount of water was added to dissolve the precipitated solid. The resulting solution was extracted with ethyl acetate (5 × 200 mL), dried overMgSO4, and evaporated to dryness product 5 (3.56 g, 75percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sulfuric acid for 18h; Heating; | |
93% | With sulfuric acid | |
92% | With sulfuric acid Reflux; |
92% | With sulfuric acid for 96h; Reflux; | 1 2.2.1 Synthesis of diethyl [2,2'-bipyridine]-4,4'-dicarboxylate 7 [2,2'-bipyridine]-4,4'-dicarboxylic acid 6 (500mg, 2mmol) was added to absolute ethanol (40mL). Concentrated sulfuric acid (95%) (0.5mL) was added to the suspension and the mixture was refluxed for 4 days. The solution was cooled to room temperature, distilled water was added (40mL) and ethanol was then evaporated. The pH was adjusted to 7 using a 5% sodium hydroxide solution. The formed precipitate was filtrated and washed with water, leading to a white powder. Yield; 92% |
91.2% | With sulfuric acid for 120h; Reflux; | 4.3.2. [2,2'-Bipyridine]-4,4'-diethyl carboxylate Ligand 1(1.00 g, 4.11 mmol) was suspended in ethanol (80 mL). Concentrated sulfuric acid (1 mL) was added and the suspension was refluxed for 5 days, and then cooled to room temperature. Water (80 mL)was added and ethanol was removed in vacuo. The aqueous layer was neutralized with 10% aqueous NaOH solution to yielda white precipitate that was collected by vacuum filtration. The crude product was washed with water and dried to yield a white solid |
91% | With sulfuric acid for 96h; Reflux; Inert atmosphere; | |
90% | With sulfuric acid Reflux; | |
90% | With sulfuric acid for 4h; Reflux; | |
85% | With thionyl chloride for 16h; Reflux; | |
85% | With sulfuric acid Reflux; | |
84% | With sulfuric acid at 85℃; for 10h; | |
76% | With sulfuric acid for 24h; Reflux; | |
76% | With sulfuric acid at 85℃; Inert atmosphere; | |
72% | With sulfuric acid at 100℃; for 72h; Inert atmosphere; | |
71% | Stage #1: ethanol; 2,2'-Bipyridine-4,4'-dicarboxylic acid With sulfuric acid Reflux; Cooling with ice; Stage #2: With ammonia In water | |
69% | With thionyl chloride; triethylamine 1.) reflux, 44 h; 2.) tetrahydrofuran, 48 h; | |
63% | With sulfuric acid for 72h; Reflux; | |
60% | With sulfuric acid In neat (no solvent) | This compound was prepared by reaction of 4,4′-dicarboxy-2,2′-bipyridine in a mixture of sulfuric acid and absolute ethanol according a published procedure (Donnici et al. 1998). Yield 60%. 1H NMR (400 MHz, chloroform-d, 7.24 ppm):8.92 (d, 2H); 8.86 (d, 2H); 7.91 (dd, 2H); 4.45 (quartet,-CH2-), 1.44 (t, -CH3). |
55% | With sulfuric acid for 48h; Reflux; | |
With sulfuric acid | ||
With sulfuric acid for 4h; Heating; | ||
With sulfuric acid at 115℃; | ||
With thionyl chloride Reflux; | ||
6.8 g | With sulfuric acid for 48h; Reflux; Inert atmosphere; | |
With sulfuric acid Inert atmosphere; Reflux; | 1A.1 (Synthesis of the mononuclear ruthenium complex (M-1) [Ru(Etcbpy)2 (H2O)2 ](OTf)2) Example 1A-1 (Synthesis of the mononuclear ruthenium complex (M-1) [Ru(Etcbpy)2 (H2O)2 ](OTf)2) Under nitrogen atmosphere, into a 500 mL three-necked flask were placed commercially available H2dcbpy (5.44 g, 22.3 mmol), concentrated sulfuric acid (10 mL) and ethanol (130 mL). The mixture was refluxed overnight. After cooling down, the mixture was neutralized. The precipitate was collected by filtration, and washed with hot water. And then, the precipitate was recrystallized with ethanol/water (95:5) and collected by filtration, to provide Etcbpy (4.92 g). | |
4.92 g | With sulfuric acid Inert atmosphere; Reflux; | A2-A Synthesis of the mononuclear ruthenium complex (M-1); [Ru(Etcbpy)2(H2O)2] (OTf)2 H2dcbpy (5.44 g, 22.3 mmol), concentrated sulfuric acid (10 mL) and ethanol (130 mL). The mixture was refluxed and reacted overnight. The reaction solution was cooled down, and then the reaction solution was neutralized. The precipitate was collected by filtration, and washed with hot water. And then, the precipitate was recrystallized with ethanol/water (95:5). The resultant crystal was collected by filtration, and then dried under vacuum, to provide Etcbpy (4.92 g). |
With sulfuric acid | ||
With sulfuric acid for 4h; Inert atmosphere; Reflux; | ||
With thionyl chloride for 12h; Reflux; | ||
With sulfuric acid for 48h; Reflux; | ||
In sulfuric acid at 100℃; Reflux; Inert atmosphere; | ||
With sulfuric acid for 72h; Reflux; | ||
With sulfuric acid | ||
With sulfuric acid | ||
With sulfuric acid at 105℃; for 40h; | ||
964 mg | With sulfuric acid at 85℃; for 24h; Inert atmosphere; | |
With sulfuric acid Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium tetrahydroborate; In ethanol; for 3h;Reflux; | Sodium borohydride (1.87g, 49mmol) was added to a suspension of diethyl [2,2'-bipyridine]-4,4'-dicarboxylate 7 (567mg, 1.89mmol) dissolved in absolute ethanol (34mL). The solution was refluxed for 3h. After cooling to room temperature, a saturated ammonium chloride solution (24mL/g of NH4Cl) was added to decompose the excess of sodium borohydride. Ethanol was evaporated under vacuum and the resulting solid was dissolved in a minimum of water using ultrasonic bath. The solution was extracted with ethyl acetate (5×34mL), dried on sodium sulfate and concentrated under vacuum to give a white powder. Yield: 91%, |
89% | With sodium tetrahydroborate; In ethanol; for 3h;Reflux; | to a suspension of the diester 4 ( 10.0 g, 33.3 mmol) in 300 ml of absolute ethanol was added sodium borohydride (25.19 g, 665.9 mmol) in one portion. The mixture was refluxed for 3 h and cooled to RT, and excess borohydride was decomposed by the dropwise addition saturated ammonium chloride solution (300 ml). Ethanol was removed under vacuum and the precipitated solid was filtered and the solid was dissolved in ethyl acetate (400 ml), washed with water ( 100 ml), dried over anhy. Na2S04and the solvent was removed under vacuum to yield the diol [2,2'-bipyridine]-4,4'-diyldimethanol 5 as awhite powder (5.9 g, 82%). |
88% | With sodium tetrahydroborate; In ethanol; at 90℃; for 3h; | Ligand 2(1.02 g, 3.40 mmol) was suspended in 200 proof ethanol (67 mL).Sodium borohydride (2.80 g, 74.0 mmol) was added and the suspension was refluxed at 90 C for 3 h. After cooling, saturated aqueous ammonium chloride (75 mL) was added and ethanol was removed in vacuo. Water was added until all white solid was dissolved.The aqueous layer was extracted with ethyl acetate (450 mL) and the combined organic layers were dried over anhydrous Na2SO4. The solvent was removed in vacuo to yielda white solid |
75% | With sodium tetrahydroborate; In ethanol; for 3h;Reflux; | To a suspension of compound 4 (6.0 g, 22.0 mmol) in 200 ml of absolute ethanol was added 16.4 g (0.434 mol) of sodium borohydride. The mixture was refluxed for 3 h and cooled to room temperature, and then 200 mL of an ammonium chloride saturated water solution was added to decompose the excess borohydride. The reaction mixture was evaporated to removed the ethanol, and a minimal amount of water was added to dissolve the precipitated solid. The resulting solution was extracted with ethyl acetate (5 × 200 mL), dried overMgSO4, and evaporated to dryness product 5 (3.56 g, 75% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In ethanol under N2; mixt. of Ru complex and ligand in EtOH refluxed for 6 h; solvent removed; purified by chromy. (SiO2, CH2Cl2-MeOH 10:1); | |
86% | In methanol at 60℃; for 4h; | |
85% | In methanol at 60℃; for 4h; | 14 4,4’-diethoxycarbonyl-2,2’-bipyridine (0.80 g, 2.68 mmol)and [Ru(p-cymene)C12]2 (0.82 g, 1.34 mmol) were added in a150 ml single neck bottle, followed by adding methanol (50 ml) and stirring at 60° C. for 4 hours to obtain a reaction mixture. The temperature ofthe reaction mixture was loweredto room temperature and a part of methanol was removed.Next, diethyl ether was added into the reaction mixture suchthat a solid product was precipitated. The solid product was collected using a suction filtration device, followed by washing the solid product using cold methanol and cold diethylether, thereby obtaining an orange solid product (0.69 g, 85%yield).The spectrum analysis for the orange solid product is: ‘H NMR (400 MHz, CDC13, 298K), ö (ppm): 10.17 (d, J=5.6 Hz, 2H), 8.64 (s, 2H), 8.28 (d, J=4.8 Hz, 2H), 6.48 (d, J=6.0 Hz,2H), 6.30 (d, J=6.0 Hz, 2H), 4.48 (q, J=7.2 Hz, 4H),2.742.68 (m, 1H), 1.81 (s, 3H), 1.43 (t, J=7.2 Hz, 6H), 1.03 (d, J=7.2 Hz, 6H). The chemical structure of the orange solidproduct is |
In methanol Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In not given with subsequent saponification; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 36% 2: 29% | In ethanol at 65℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 12% 2: 13% | In ethanol at 65℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 34% 2: 36% | In ethanol at 65℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 36% 2: 18% | In ethanol at 65℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.7% | Stage #1: bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III); 4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine In ethanol for 68h; Reflux; Stage #2: ammonium hexafluorophosphate In water; acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 4,4′-bis(2-hexylthiophene-5-yl)-2,2′-bipyridine In methanol at 60℃; for 4h; Inert atmosphere; Stage #2: 4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine In N,N-dimethyl-formamide at 140℃; for 4h; Darkness; Stage #3: 5,5’-bis(trifluoromethyl)-2H,2’H-3,3’-bipyrazole In toluene for 8h; Reflux; Inert atmosphere; | 3 Example 3 Example 3 [0064] Dichloro(p-cymene) ruthenium(II) dimer (100 mg, 0.163 mmol) and 4,4′-bis(5-hexylthiophen-2-yl)-2,2′-bipyridine (159 mg, 0.326 mmol) were disposed in a 150 ml reaction flask, followed by adding 50 ml methanol and heating at 60° C. for 4 hours under a nitrogen gas atmosphere. After the reaction was finished, the reaction mixture was cooled to room temperature, followed by reduced pressure distillation to remove methanol. Next, the mixture was added with 4,4′-diethoxycarbonyl-2,2′-bipyridine (97.879 mg, 0.326 mmol) and 50 ml dimethylformamide, followed by heating at 140° C. for 4 hours under a dark condition. After the reaction was finished, the reaction mixture was cooled to room temperature, followed by reduced pressure distillation to remove dimethylformamide. Thereafter, the product of Synthesis Example 2 (92.5 mg, 0.343 mmol), sodium acetate (0.134 g, 1.63 mmol) and 50 ml toluene were added in the reaction flask, followed by heating under reflux for 8 hours under a nitrogen gas atmosphere. After the reaction was finished, the mixture was cooled to room temperature and toluene was removed by virtue of reduced pressure distillation. Next, 100 ml dichloromethane and 100 ml deionized water were added to perform partition extraction, and the dichloromethane layer was collected and further added with 100 ml deionized water, followed by repeating the partition extraction step three times. The collected dichloromethane layer was subjected to column chromatography, in which a mixture of ethyl acetate and hexane (ethyl acetate:hexane=1:1) was used as an eluent to obtain a black solid product (0.173 g, 0.15 mmol, 46% yield). [0065] The black solid product (0.1 g, 0.086 mmol) was dissolved in 50 ml acetone, followed by adding 5 ml of a sodium hydroxide solution (2M) and stirring at room temperature for 8 hours. Next, acetone was removed by means of reduced pressure distillation, followed by adding 20 ml deionized water and adjusting pH of the reaction mixture to about 3 using a hydrogen chloride solution (2N). A filtration process was conducted and a filter cake was collected, followed by washing the filter cake using deionized water and dichloromethane to obtain a dark brown solid product (80.9 mg, 0.073 mmol, 85% yield) (hereinafter referred to as ruthenium complex A-3). [0066] The spectrum analysis for the ruthenium complex A-3 is: 1H NMR (400 MHz, d6-dimethyl sulfoxide, 294K), δ (ppm): 8.77 (s, 2H), 8.73 (s, 1H), 8.68 (s, 1H), 7.87 (br.s, 1H), 7.77 (d, 3JHH=6 Hz, 1H), 7.72 (d, 3JHH=6 Hz, 1H), 7.627.49 (m, 6H), 7.32 (br.s 1H), 6.95 (m, 2H), 6.55 (s, 1H), 6.53 (s, 1H), 2.842.80 (m, 6H), 1.291.26 (m, 16H), 0.850.84 (m, 6H); 19F-{1H} NMR (470 MHz, d6-dimethyl sulfoxide, 298K), δ (ppm): -57.3 (s, CF3), -57.4 (s, CF3). [0067] The chemical structure of the ruthenium complex A-3 is |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 4,4′-bis(2-hexylthiophene-5-yl)-2,2′-bipyridine In methanol at 60℃; for 4h; Inert atmosphere; Stage #2: 4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine In N,N-dimethyl-formamide at 140℃; for 4h; Darkness; Stage #3: C6H2F6N6 In toluene for 8h; Reflux; Inert atmosphere; | 4 Example 4 Example 4 [0068] Dichloro(p-cymene) ruthenium(II) dimer (100 mg, 0.163 mmol) and 4,4′-bis(5-hexylthiophen-2-yl)-2,2′-bipyridine (159 mg, 0.326 mmol) were disposed in a 150 ml reaction flask, followed by adding 50 ml methanol and heating at 60° C. for 4 hours under a nitrogen gas atmosphere. After the reaction was finished, the reaction mixture was cooled to room temperature, followed by reduced pressure distillation to remove methanol. Next, the mixture was added with 4,4′-diethoxycarbonyl-2,2′-bipyridine (97.879 mg, 0.326 mmol) and 50 ml dimethylformamide, followed by heating at 140° C. for 4 hours under a dark condition. After the reaction was finished, the reaction mixture was cooled to room temperature, followed by reduced pressure distillation to remove dimethylformamide. Thereafter, the product of Synthesis Example 1 (93.0 mg, 0.342 mmol), sodium acetate (0.134 g, 1.63 mmol) and 50 ml toluene were added in the reaction flask, followed by heating under reflux for 8 hours under a nitrogen gas atmosphere. After the reaction was finished, the mixture was cooled to room temperature and toluene was removed by virtue of reduced pressure distillation. Next, 100 ml dichloromethane and 100 ml deionized water were added to perform partition extraction, and the dichloromethane layer was collected and further added with 100 ml deionized water, followed by repeating the partition extraction step three times. The collected dichloromethane layer was subjected to column chromatography, in which a mixture of ethyl acetate and hexane (ethyl acetate:hexane=1:1) was used as an eluent to obtain a black solid product (0.171 g, 0.147 mmol, 43% yield). The black solid product (0.1 g, 0.086 mmol) was dissolved in 50 ml acetone, followed by adding 5 ml of a sodium hydroxide solution (2M) and stirring at room temperature for 8 hours. Next, acetone was removed by means of reduced pressure distillation, followed by adding 20 ml deionized water and adjusting pH of the reaction mixture to about 3 using a hydrogen chloride solution (2N). A filtration process was conducted and a filter cake was collected, followed by washing the filter cake using deionized water and dichloromethane to obtain a dark brown solid product (79.9 mg, 0.072 mmol, 84% yield) (hereinafter referred to as ruthenium complex A-4). [0069] The spectrum analysis for the ruthenium complex A-4 is: 1H NMR (400 MHz, d6-dimethyl sulfoxide, 294K), δ (ppm): 9.07 (s, 1H), 9.06 (s, 1H), 8.92 (s, 1H), 8.91 (s, 1H), 8.18 (d, 3JHH=6 Hz, 1H), 8.107.90 (m, 4H), 7.80 (d, 3JHH=5.8 Hz, 1H), 7.76 (d, 3JHH=5.8 Hz, 1H), 7.59 (d, 3JHH=6 Hz, 1H), 7.52 (d, 3JHH=6 Hz, 1H), 7.43 (d, 3JHH=4.4 Hz, 1H), 7.05 (m, 2H), 2.85 (q, 3JHH=8 Hz, 4H), 1.64 (q, 3JHH=8 Hz, 4H), 1.281.26 (m, 12H), 0.860.84 (m, 6H); 19F-{1H} NMR (470 MHz, d6-dimethyl sulfoxide, 294K), δ (ppm): -61.62 (s, CF3), -61.59 (s, CF3); MS (FAB): m/z 1104 (1105) [M+1]+. [0070] The chemical structure of the ruthenium complex A-4 is |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Example 5 [0071] Os3(CO)12 (0.2 g, 0.221 mmol), 4,4?-di-tert-butyl-2,2?-bipyridine (173 mg, 0.684 mmol) and the product of Synthesis Example 1 (185 mg, 0.684 mmol) were disposed in a 150 ml reaction flask, followed by adding 50 ml diethylene glycol monomethyl ether and heating at 180 C. for 24 hours under a nitrogen gas atmosphere. After the reaction was finished, the reaction mixture was cooled to room temperature, followed by reduced pressure distillation to remove diethylene glycol monomethyl ether. Next, the mixture was subjected to column chromatography, in which a mixture of ethyl acetate and hexane (ethyl acetate:hexane=1:1) was used as an eluent. Thereafter, recrystallization was conducted using dichloromethane and hexane to obtain a yellow solid product (0.162 g, 0.205 mmol, 31% yield). The yellow solid product (0.1 g, 0.127 mmol) was dissolved in diethylene glycol monomethyl ether, followed by adding trimethylamine N-oxide (20 mg, 0.267 mmol) and stirring at room temperature for 1 hour. Thereafter, the mixture was added with 4,4?-diethoxycarbonyl-2,2?-bipyridine (41.98 mg, 0.14 mmol), followed by heating under reflux for 24 hours under a nitrogen gas atmosphere. Next, diethylene glycol monomethyl ether was removed by means of reduced pressure distillation. Thereafter, the mixture was subjected to column chromatography, in which a mixture of ethyl acetate and hexane (ethyl acetate:hexane=1:2) was used as an eluent to obtain a black solid product (39.6 mg, 0.041 mmol, 41.9% yield). [0072] The black solid product (0.1 g, 0.103 mmol) was dissolved in 50 ml acetone, followed by adding 5 ml of a sodium hydroxide solution (2M) and stirring at room temperature for 8 hours. Next, acetone was removed by means of reduced pressure distillation, followed by adding 20 ml deionized water and adjusting pH of the reaction mixture to about 3 using a hydrogen chloride solution (2N). A filtration process was conducted and a filter cake was collected, followed by washing the filter cake using deionized water and dichloromethane to obtain a dark brown solid product (86 mg, 0.088 mmol, 86% yield) (hereinafter referred to as osmium complex A-5). [0073] The spectrum analysis for the osmium complex A-5 is: 1H NMR (400 MHz, CDCl3, 294K), delta (ppm): 8.99 (s, 1H), 8.97 (s, 1H), 8.74 (s, 1H), 8.66 (s, 1H), 7.98 (d, 3JHH=6 Hz, 1H), 7.95 (d, 3JHH=6 Hz, 1H), 7.68 (d, 3JHH=5.6 Hz, 1H), 7.65 (d, 3JHH=4.8 Hz, 1H), 7.52 (d, 3JHH=6.4 Hz, 1H), 7.42 (d, 3JHH=6 Hz, 1H), 7.37 (d, 3JHH=6 Hz, 1H), 7.27 (d, 3JHH=4.8 Hz, 1H), 1.40 (s, 9H), 1.34 (S, 9H); 19F-{1H} NMR (470 MHz, d5-dimethyl sulfoxide, 294K), delta (ppm): -61.55 (s, CF3), -61.8 (s, CF3); MS (FAB): m/z 974 [M]+. [0074] The chemical structure of the osmium complex A-5 is |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.1% | Stage #1: C18H26Cl3Ru2; 4-(hydroxymethyl)-4'-methyl-2,2'-bipyridine In N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere; Darkness; Stage #2: 4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine In N,N-dimethyl-formamide at 140℃; for 4h; Stage #3: ammonium thiocyanate In N,N-dimethyl-formamide at 140℃; for 4h; | Synthesis of the model compound, Ru-bpy The synthesis of the low molar mass ruthenium complexRu-bpy was conducted similarly to as described in literature[34]. Compound 2 (60 mg, 0.30 mmol) was added to a DMF(30 mL) solution of compound 5 (87 mg, 0.15 mmol) in a flaskprotected by argon flushing, and stirred at 80 C for 4 h withoutexposure to light. Subsequently, compound 6 (83 mg, 0.30 mmol)was added and the reaction mixture was stirred at 140 C for 4 h.Finally, an excess of NH4NCS (46 mg, 0.60 mmol) was added tothe resulting deep black solution and the reaction continued foranother 4 h at the same temperature. Subsequently, the reactionmixture was cooled to room temperature and the solvent wasremoved. Water was added to resuspend the precipitate, whichwas collected and washed with water and ethanol several times,and then dried under vacuum to yield a black powder of Ru-bpy.(136 mg, Yield: 83.1%). From the 1H NMR spectrum, the productof Ru-bpy could be recognized as a mixture of stereoisomers. 1HNMR (400 MHz, DMSO, d, ppm): 9.50 (d, J = 5.5 Hz, 2H, ArH), 9.21(m, 2H, ArH), 9.09-8.97 (m, 4H, ArH), 8.68 (s, 2H, ArH), 8.52 (s,2H, ArH), 8.36 (m, 2H, ArH), (m, 4H, ArH), 7.30 (s, 2H, ArH), 7.19 (d, J = 11.2 Hz, 2H, ArH), 7.06(s, 2H, ArH), 5.89 (s, 1H, AOH), 5.64 (s, 1H, AOH), 4.90 (s, 2H,ArACH2A), 4.61 (s, 2H, ArACH2A), 4.51 (s, 2H, ACH2A), 4.37(d, J = 7.0 Hz, 2H, ACH2A), 2.68 (s, 3H, ArACH3), 2.41 (s, 3H,ArACH3), 1.45 (t, J = 6.7 Hz, 6H, ACH3), 1.30 (dd, J = 17.5, 11.4 Hz,6H, ACH3). IR (KBr disc): m (SCN): 2102 cm1, m (COO):1723 cm1, m (CN): 1613 cm1, m (CC): 1400 cm1.8.03-7.78 (m, 4H, ArH), 7.74-7.54 |
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 |
---|---|---|
94% | In n-heptane; toluene at 60℃; for 20h; Inert atmosphere; |
Tags: 1762-42-1 synthesis path| 1762-42-1 SDS| 1762-42-1 COA| 1762-42-1 purity| 1762-42-1 application| 1762-42-1 NMR| 1762-42-1 COA| 1762-42-1 structure
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Code | Phrase |
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P265 | Wash skin thouroughly after handling. |
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P272 | Contaminated work clothing should not be allowed out of the workplace. |
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Code | Phrase |
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P378 | |
P380 | Evacuate area. |
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Code | Phrase |
H200 | Unstable explosive |
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H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
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H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
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H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
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Health hazards | |
Code | Phrase |
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H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
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H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
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 |
Sorry,this product has been discontinued.
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