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CAS No. : | 179873-48-4 | MDL No. : | MFCD11042460 |
Formula : | C11H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NYRALBSJJJBAMN-UHFFFAOYSA-N |
M.W : | 184.19 | Pubchem ID : | 10866997 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
50% | With triethylamine; triphenylphosphine In dichloromethane 1.) -60 deg C, 20 min, 2.) -60 deg C to r.t.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With acetic acid for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | In toluene at 0℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With air In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | In propionic acid Heating; | |
16% | With propionic acid at 140℃; for 0.75h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With potassium carbonate In water at 100℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.4% | In tetrahydrofuran for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | Stage #1: pyrene-1-aldehyde; 2,2’-bipyridine-5-carbaldehyde; 1,4-bis(triphenylphosphoniomethyl)-2,5-dioctyloxybenzene dibromide With sodium hydride In tetrahydrofuran at 30℃; for 40h; Stage #2: With iodine In dichloromethane at 20℃; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | Stage #1: benzaldehyde; 2,2’-bipyridine-5-carbaldehyde; 1,4-bis(triphenylphosphoniomethyl)-2,5-dioctyloxybenzene dibromide With lithium ethoxide In ethanol; dichloromethane at 20℃; for 0.5h; Stage #2: With iodine In dichloromethane at 20℃; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium periodate In tetrahydrofuran; water at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ethanol / 24 h / 20 °C 2: NaBH4 / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: methanol / 24 h / 20 °C 2: 80 percent / NaBH4 / ethanol / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 63 percent / I2 / 6 h / Heating 2: 72 percent / NH4OAc / formamide / 6 h / 80 °C 3: 43 percent / NBS, AIBN / CCl4 / 7 h / Heating; Irradiation 4: 83 percent / CCl4 / 5 h / Heating 5: 50 percent / aq. AcOH / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 83 percent / CCl4 / 5 h / Heating 2: 50 percent / aq. AcOH / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 72 percent / NH4OAc / formamide / 6 h / 80 °C 2: 43 percent / NBS, AIBN / CCl4 / 7 h / Heating; Irradiation 3: 83 percent / CCl4 / 5 h / Heating 4: 50 percent / aq. AcOH / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 50 percent / PPh3, NEt3 / CH2Cl2 / 1.) -60 deg C, 20 min, 2.) -60 deg C to r.t. 2: 44 percent / BuLi / hexane / 2 h / -60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: 2,2’-bipyridine-5-carbaldehyde In tetrahydrofuran at 0 - 20℃; for 6.5h; | 5-vinyl-2,2'-bipyridine (1): To a solution of [PPh3Me]Br (4.25 g, 11.9 mmol) in dry THF (100 mL) was added dropwise n-BuLi (2.0 M, 5.5 mL, 11.00 mmol) at 0 °C. The reaction mixture was stirred for 30 mins at room temperature, and then a solution of compound I (1.69 g, 9.16 mmol) in 50 mL of dry THF was added dropwise at 0 °C. The reaction was stirred for 30 min at 0 °C, and then the cooling bath was removed. The reaction mixture was stirred for another 6 h at room temperature and then quenched by addition of saturated aqueous NaHCO3 and stirring for another 15 min. The reaction mixture was extracted with ethyl acetate and the combined organic phase was washed with brine, dried over Na2SO4, filtrated and concentrated in vacuum. The residue was purified by flash chromatography (PE/EA = 5:1) to give compound 1 (1.37 g, yield: 82%) as a white solid. 1H NMR (500 MHz, CDCl3): δ 8.66 (d, J = 2.5 Hz, 2H), 8.37 (t, J = 9.0 Hz, 2H), 7.84 (dd, J12 = 2.5 Hz, J13 = 8.0 Hz, 1H), 7.76~7.80 (m, 1H), 7.25~7.28 (m, 1H), 6.74 (dd, J12 = 11.0 Hz, J13 = 18.0 Hz, 1H), 5.87 (d, J = 17.5 Hz, 1H), 5.39 (d, J = 11.0 Hz, 1H); 13C NMR (500 MHz, CDCl3): δ 155.9, 155.3, 149.2, 147.8, 136.9, 133.5, 133.3, 133.1, 123.7, 121.1, 120.9, 116.4; MS (MALDI-TOF): m/z 183.15 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / 0 - 20 °C 1.2: 6.5 h / 0 - 20 °C 2.1: sodium iodide / N,N-dimethyl-formamide / 0.5 h / 100 °C / Inert atmosphere 2.2: 4 h / 100 °C / Inert atmosphere 3.1: triethyl phosphite / 4 h / 120 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / 0 - 20 °C 1.2: 6.5 h / 0 - 20 °C 2.1: sodium iodide / N,N-dimethyl-formamide / 0.5 h / 100 °C / Inert atmosphere 2.2: 4 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide; <i>tert</i>-butyl alcohol at 20℃; for 19h; Cooling with ice; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide; <i>tert</i>-butyl alcohol / 19 h / 20 °C / Cooling with ice; Inert atmosphere 2: diisopropyl-carbodiimide / chloroform / 4 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine In toluene for 72h; Reflux; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In N,N-dimethyl-formamide at 70℃; for 16h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In N,N-dimethyl-formamide at 70℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; diethyl ether / -78 °C / Inert atmosphere 1.2: 3 h / -78 - 20 °C 2.1: triphenylphosphine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 72 h / 125 °C / Schlenk technique; Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triphenylphosphine; copper (I) iodide; tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide / 72 h / 125 °C / Schlenk technique; Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 16 h / 20 °C | ||
Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium / toluene / 4 h / 120 °C / Microwave irradiation 2: hydrogenchloride / water monomer; tetrahydrofuran / 15 h / 15 - 30 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triphenylphosphine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 72 h / 125 °C / Schlenk technique; Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With trifluoroacetic acid In dichloromethane at 20℃; for 16h; | Synthesis of 2,2-bipyridin-5-carbaldehyde (3) 5-(1,3-dmL)was added and the reaction mixture was stirred vigorously for16 h at room temperature. The reaction was stopped by addition of Na2CO3(sat., aq., 10 mL). After phase separation the aqueous phase was extracted with CH2Cl2(3 × 15 mL). The combined organic phases were washed with a solution of NaCl/NaOH (sat., aq.,5 mL/6 M, aq., 1 mL), dried over Na2SO4 and the solvent removed in vacuum. Additional drying under high vacuum gave the desired product 3 (702 mg, quant.) as yellow solid which was used without further purification. |
With hydrogenchloride In tetrahydrofuran; water monomer at 15 - 30℃; for 15h; | 63.2 Step 2: Preparation of [2,2’-dipyridyl]-5-carbaldehyde (Compound 130c) Diluted hydrochloric acid (5.0 mL, 3 N) was added dropwise into a solution of Compound 130b (100 mg) inTHF (5.0 mL). The mixture was kept for reaction at room temperature for 15 h. After completion of the reaction, thereaction mixture was adjusted to a pH of about 10 by slowly adding a saturated sodium bicarbonate solution dropwise,and then extracted with EA. The organic phase was dried over anhydrous sodium sulfate, filtered, and then concentrated,to provide Compound 130c (45 mg), which was directly used for next step reaction without purification. MS m/z (ESI):185.2 [M+H]+. | |
With hydrogenchloride In tetrahydrofuran; water monomer at 15 - 30℃; for 15h; | 63.2 Step 2: Preparation of [2,2’-dipyridyl]-5-carbaldehyde (Compound 130c) Diluted hydrochloric acid (5.0 mL, 3 N) was added dropwise into a solution of Compound 130b (100 mg) inTHF (5.0 mL). The mixture was kept for reaction at room temperature for 15 h. After completion of the reaction, thereaction mixture was adjusted to a pH of about 10 by slowly adding a saturated sodium bicarbonate solution dropwise,and then extracted with EA. The organic phase was dried over anhydrous sodium sulfate, filtered, and then concentrated,to provide Compound 130c (45 mg), which was directly used for next step reaction without purification. MS m/z (ESI):185.2 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 16h; | Synthesis of 2,2-bipyridin-5-methylamino(ethyl-2-(tert-butylcarbamate) 2,2-Bipyridine-5-carbaldehyd (3) (350 mg, 1.9 mmol, 1.0 eq) and tert-butyl-(2-aminoethyl)-carbamate (320 mg, 2.00 mmol,1.05 eq) were dissolved in EtOH (25 mL) and degassed with 3 cycles high vacuum/argon. Then Pd/C (10% w/w, 50 mg) was added and the reaction flask was sealed with a septum. To exchange the argon atmosphere against a hydrogen atmosphere a small balloon wasfilled with hydrogen. Then the flask was evacuated until the solvent started to boil and the flask was filled with hydrogen from the balloon through the septum. The reaction mixture was stirred under hydrogen atmosphere for 16 h at room temperature. Then the catalyst was removed by filtration (celite) and the filter cake was washed with additional EtOH (25 mL). Removal of the solvent in vacuum and cleaning via LC (SiO2, DCM/MeOH/NEt3= 100/10/1) yielded the desired product (554 mg, 89%) as pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridinium p-toluenesulfonate / toluene / 2 h / Dean-Stark; Reflux 2: triphenylphosphine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 72 h / 125 °C / Schlenk technique; Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: oxalyl dichloride; triethylamine / dimethyl sulfoxide / 2.5 h / -78 - 20 °C 2: pyridinium p-toluenesulfonate / toluene / 2 h / Dean-Stark; Reflux 3: triphenylphosphine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 72 h / 125 °C / Schlenk technique; Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triethylsilane; tris-(dibenzylideneacetone)dipalladium(0); carbon monoxide; 1,3-bis-(diphenylphosphino)propane; sodium carbonate at 90℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In acetonitrile at 70℃; for 24h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | Stage #1: 2,4-dimethyl-1H-pyrrole; 2,2’-bipyridine-5-carbaldehyde With trifluoroacetic acid In dichloromethane at 20℃; for 3h; Inert atmosphere; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 0.166667h; Stage #3: With boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In water for 6h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.7% | Stage #1: pyridine-4-carbaldehyde; pyrrole; 2,2’-bipyridine-5-carbaldehyde In propionic acid at 140℃; for 0.75h; Darkness; Stage #2: zinc(II) acetate dihydrate In methanol; chloroform at 20℃; for 4.5h; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine In toluene for 72h; Inert atmosphere; Schlenk technique; | Synthesis of 5-aldehyde-2, 2-bipyridine (CHO-bpy) L1 Pd(PPh3)2Cl2 (52.0 mg, 0.08 mmol), PPh3 (38.5 mg, 0.15 mmol), 2-(tributylstannylpyridine)(552.2 mg, 1.50 mmol), 6-bromo-3-pyridinecarbaldehyde(329.0 mg, 1.77 mmol) and toluene (20.0 mL) were added to anoven-dried Schlenk flask. The resulting mixture was stirred for 72 hunder N2 atmosphere. Then the reaction mixture was cooled to roomtemperature and the solvent was removed under reduced pressure. Theobtained solid was dissolved in CH2Cl2 (25.0 mL) and washed with asaturated NH4Cl solution (15.0 mL). The aqueous phase was extractedwith CH2Cl2. The organic layers were combined, the solvent wasremoved under reduced pressure and the crude product was purified bysilica gel column chromatography (EA/PE 3/7) to give L1 as a whitesolid. Yield: 47% (130.0 mg), mp: 223 °C (76 mmHg), IR (KBr): 1699,1584, 1553, 1445, 1250, 1034, 846 cm-1. 1H NMR (500 MHz, CDCl3): δ10.17 (1H, s), 9.13 (1H, s), 8.73 (1H, d, J= 3.9 Hz), 8.61 (1H, d, J= 8.2Hz), 8.51 (1H, d, J= 7.9 Hz), 8.29 (1H, dd, J =8.2, 3.5 Hz), 7.87 (1H, t,J =7.0 Hz), 7.42-7.36 (1H, m), 13C NMR (125 MHz, CDCl3): δ190.9,160.8, 154.7, 151.8, 149.5, 137.5, 137.2, 131.2, 125.0, 122.4, 121.5ppm, HRMS calcd [M+H]+: m/z 185.0715; found: 185.0712, Elementalanalysis calcd (%) for C11H8N2O: C 71.73, H 4.38, N 15.21; found: C71.65, H 4.40, N 15.30. 1H and 13C NMR data are in agreement with those published [69]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | Stage #1: ruthenium trichloride; 2,2’-bipyridine-5-carbaldehyde In ethanol; water for 24h; Reflux; Inert atmosphere; Schlenk technique; Stage #2: ammonium hexafluorophosphate | Synthesis of [Ru(CHO-bpy)3](PF6)2 P1 64.4 mg of L1 (0.35 mmol) in 15 mL of EtOH was added to a solution of RuCl3 (20.7 mg, 0.10mmol) in 20 mL of EtOH/H2O (3/1). The reaction mixture was refluxedfor 24 h, and then cooled to room temperature. After the solvent wasevaporated, the residue was dissolved in a small amount of water, andthen the aqueous solution was washed with CH2Cl2. A saturated solutionof NH4PF6 was added to yield red precipitate of the product, which wasfurther purified by neutral aluminum oxide column chromatographywith CH2Cl2/MeOH (10/1) as eluent. The target Ru(II) complex P1 wasisolated as a red solid. Yield: 54% (53.0 mg), mp: 469 °C (76 mmHg), IR(KBr): 1761, 1623, 1583, 1423, 1295, 810 cm-1, 1H NMR (500 MHz,DMSO-d6) 9.89 (3H, dd, J= 5.0, 2.5 Hz), 9.03 (3H, s), 8.97 (3H, s),8.56 (3H, t, J= 5.0 Hz), 8.16 (6H, dd, J= 5.0, 2.5 Hz), 7.83 (3H, dd, J 5.0, 2.5 Hz), 7.61 (3H, s), 13C NMR (125 MHz, DMSO-d6): 190.9,160.9, 156.2, 151.5, 149.3, 138.8, 133.6, 129.3, 126.4, 126.2, 125.1ppm, HRMS calcd [M-PF6]+: m/z 799.0595; found: 799.0587,Elemental analysis calcd (%) for C33H24F12N6O3P2Ru: C 42.01, H 2.56, N8.91; Found: C 42.15, H 2.47, N 8.78. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40 mg | Stage #1: 2-(6-{3,6-diazabicyclo[3.1.1]heptan-3-yl}pyridin-3-yl)-6-methyl-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine; 2,2’-bipyridine-5-carbaldehyde With titanium isopropoxide In tetrahydrofuran at 72℃; for 10h; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 72℃; for 6h; | 63.3 Step 3: Preparation of 2-(6-(6-([[2,2’-dipyridyl]-5-ylmethyl)-3,6-diazabicyclo[3.1.1]heptan-3-yl)pyridin-3-yl)-6-methyl-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine (Compound 130) Compound 1g (50 mg), Compound 130c (25.4 mg), and tetraisopropyl titanate (156.8 mg) were added into dryTHF (5 mL), and the mixture was stirred at 72 °C for 10 h. Then, sodium triacetoxyborohydride (146.2 mg) was added,and the mixture was kept for reaction at 72 °C for 6 h. After completion of the reaction, the mixture was crudely purifieddirectly by silica gel column chromatography (DCM:MeOH=10:1), and then separated and purified by Prep-HPLC toprovide Compound 130 (40 mg). MS m/z (ESI): 531.3 [M+H]+.1H NMR (400 MHz, DMSO-d6) δ 11.97 (s, 1H), 9.65 (s, 1H), 9.13 (d, J= 2.2 Hz, 1H), 8.75-8.57 (m, 2H), 8.44(dd, J = 8.9, 2.3 Hz, 1H), 8.35 (dd, J = 9.7, 8.2 Hz, 2H), 7.93 (ddd, J = 8.3, 5.9, 1.9 Hz, 2H), 7.44 (ddd, J= 7.5, 4.8, 1.1Hz, 1H), 7.08 - 6.57 (m, 2H), 6.31 (s, 1H), 3.82-3.57 (m, 8H), 2.63 - 2.56 (m, 1H), 2.33 (s, 3H), 2.26 (s, 3H), 1.61 (d, J=8.4 Hz, 1H). |
40 mg | Stage #1: 2-(6-{3,6-diazabicyclo[3.1.1]heptan-3-yl}pyridin-3-yl)-6-methyl-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine; 2,2’-bipyridine-5-carbaldehyde With titanium isopropoxide In tetrahydrofuran at 72℃; for 10h; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 72℃; for 6h; | 63.3 Step 3: Preparation of 2-(6-(6-([[2,2’-dipyridyl]-5-ylmethyl)-3,6-diazabicyclo[3.1.1]heptan-3-yl)pyridin-3-yl)-6-methyl-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine (Compound 130) Compound 1g (50 mg), Compound 130c (25.4 mg), and tetraisopropyl titanate (156.8 mg) were added into dryTHF (5 mL), and the mixture was stirred at 72 °C for 10 h. Then, sodium triacetoxyborohydride (146.2 mg) was added,and the mixture was kept for reaction at 72 °C for 6 h. After completion of the reaction, the mixture was crudely purifieddirectly by silica gel column chromatography (DCM:MeOH=10:1), and then separated and purified by Prep-HPLC toprovide Compound 130 (40 mg). MS m/z (ESI): 531.3 [M+H]+.1H NMR (400 MHz, DMSO-d6) δ 11.97 (s, 1H), 9.65 (s, 1H), 9.13 (d, J= 2.2 Hz, 1H), 8.75-8.57 (m, 2H), 8.44(dd, J = 8.9, 2.3 Hz, 1H), 8.35 (dd, J = 9.7, 8.2 Hz, 2H), 7.93 (ddd, J = 8.3, 5.9, 1.9 Hz, 2H), 7.44 (ddd, J= 7.5, 4.8, 1.1Hz, 1H), 7.08 - 6.57 (m, 2H), 6.31 (s, 1H), 3.82-3.57 (m, 8H), 2.63 - 2.56 (m, 1H), 2.33 (s, 3H), 2.26 (s, 3H), 1.61 (d, J=8.4 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium / toluene / 4 h / 120 °C / Microwave irradiation 2: hydrogenchloride / water monomer; tetrahydrofuran / 15 h / 15 - 30 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With acetic acid In methanol at 70℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With potassium <i>tert</i>-butylate In toluene at 20℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 5-(hydroxymethyl)-2,2'-bipyridine With oxalyl dichloride In dichloromethane; dimethyl sulfoxide at -78℃; Stage #2: With triethylamine at 20℃; |
Tags: 179873-48-4 synthesis path| 179873-48-4 SDS| 179873-48-4 COA| 179873-48-4 purity| 179873-48-4 application| 179873-48-4 NMR| 179873-48-4 COA| 179873-48-4 structure
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P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
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 |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
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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