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Product Details of [ 146581-82-0 ]

CAS No. :146581-82-0 MDL No. :MFCD11042459
Formula : C11H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 184.19 Pubchem ID :-
Synonyms :

Safety of [ 146581-82-0 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 146581-82-0 ]

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

  • Downstream synthetic route of [ 146581-82-0 ]

[ 146581-82-0 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 495-69-2 ]
  • [ 146581-82-0 ]
  • 4-(2,2'-bipyridin-4-ylmethylene)-2-phenyl-5(4H)-oxazolone [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With sodium acetate; acetic anhydride at 90℃; for 1h;
  • 2
  • [ 56100-19-7 ]
  • [ 146581-82-0 ]
YieldReaction ConditionsOperation in experiment
36% With selenium(IV) oxide; water In 1,4-dioxane Heating;
Multi-step reaction with 2 steps 1: 94 percent / dimethylformamide / 18 h / 140 °C 2: 82 percent / NaIO4 / tetrahydrofuran; H2O / 4 h / 20 °C
  • 3
  • [ 1122-62-9 ]
  • [ 146581-82-0 ]
  • [ 745016-36-8 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: 2-acetylpyridine; 2,2'-bipyridine-4-carboxaldehyde With sodium hydroxide In methanol at 20℃; for 1h; Stage #2: With ammonium acetate In ethanol Heating; Further stages.;
  • 4
  • [2-(N,N-dimethylamino)vinyl]-2,2'-bipyridine [ No CAS ]
  • [ 146581-82-0 ]
YieldReaction ConditionsOperation in experiment
82% With sodium periodate In tetrahydrofuran; water at 20℃; for 4h;
  • 5
  • [ 13610-02-1 ]
  • [ 146581-82-0 ]
  • [ 896732-96-0 ]
YieldReaction ConditionsOperation in experiment
45% With sulfuric acid; acetic acid for 17h;
  • 6
  • [ 26482-00-8 ]
  • [ 146581-82-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 40 percent / ammonium acetate / methanol / 65 °C 2: 94 percent / dimethylformamide / 18 h / 140 °C 3: 82 percent / NaIO4 / tetrahydrofuran; H2O / 4 h / 20 °C
  • 7
  • [ 146581-82-0 ]
  • [ 146581-80-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 75 percent / acetic anhydride, sodium acetate / 1 h / 90 °C 2: red phosphorous, 47percent aq. hydriodic acid, acetic anhydride / 3.5 h / Heating 3: HCl(g)
  • 8
  • [ 146581-82-0 ]
  • N-(9-fluorenylmethoxycarbonyl)-(S)-2-amino-3-(2,2'-bipyridin-4-yl)propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 75 percent / acetic anhydride, sodium acetate / 1 h / 90 °C 2: red phosphorous, 47percent aq. hydriodic acid, acetic anhydride / 3.5 h / Heating 3: HCl(g) 4: 0.2 M aq. NaHCO3 / 2 h / Ambient temperature; alkaline protease ( from Bacillus licheniformis) 5: 85 percent / 10percent aq. NaCO3 / dioxane / 1.5 h
  • 9
  • [ 146581-82-0 ]
  • 2-amino-3-(2,2'-bipyridin-4-yl)propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / acetic anhydride, sodium acetate / 1 h / 90 °C 2: red phosphorous, 47percent aq. hydriodic acid, acetic anhydride / 3.5 h / Heating
  • 10
  • [ 146581-82-0 ]
  • [ 146581-78-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 75 percent / acetic anhydride, sodium acetate / 1 h / 90 °C 2: red phosphorous, 47percent aq. hydriodic acid, acetic anhydride / 3.5 h / Heating 3: HCl(g) 4: 0.2 M aq. NaHCO3 / 2 h / Ambient temperature; alkaline protease ( from Bacillus licheniformis)
  • 11
  • [ 21211-65-4 ]
  • [ 939-97-9 ]
  • [ 146581-82-0 ]
  • 5-(4-tert-butylphenyl)-15-(4-bipyridyl)porphyrin [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% Stage #1: di(pyrrol-2-yl)methane; 4-tert-Butylbenzaldehyde; 2,2'-bipyridine-4-carboxaldehyde With boron trifluoride diethyl etherate In methanol; dichloromethane for 96h; Inert atmosphere; Schlenk technique; Darkness; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In methanol; dichloromethane for 1h; Inert atmosphere; Schlenk technique; Darkness; Stage #3: With triethylamine In methanol; dichloromethane for 1.5h; Inert atmosphere; Schlenk technique; Darkness;
  • 12
  • [ 867-13-0 ]
  • [ 146581-82-0 ]
  • (E)-3-(2,2'-bipyridine-4-yl)-2-propenoic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With potassium carbonate In tetrahydrofuran at 20℃; for 0.583333h; Reflux; Stage #2: 2,2'-bipyridine-4-carboxaldehyde In tetrahydrofuran at 110℃; for 2h; Microwave irradiation; E)-3-(2,20-Bipyridine-4-yl)-2-propenoic acid ethyl ester(7, C15H14N2O2) Dry potassium carbonate (1.3 g, 9.24 mmol) and 2.1 gtriethyl phosphonoacetate were suspended in 10 cm3 of anhydrous THF and stirred at room temperature for 15 minbefore the suspension was refluxed for 20 min (b) Microwave assisted synthesisAfter cooling the suspension to room temperature, it wastransferred into a microwave vessel and 1.1 g of 6(6.16 mmol) in 2.0 cm3 anhydrous THF were added. Thevessel was sealed and heated to 110 C in a way that duringa period of 10 min 110 C had to be reached using amaximum power of 1000 W. The reaction temperaturethen was maintained for 2 h after which the vessel wasallowed to cool down to room temperature. Purification procedure: After cooling 20.0 cm3 of a 10%potassium carbonate solution was added. The mixture wasextracted three times with 30 cm3 ethyl acetate. Theorganic phase was dried over sodium sulfate and the solventwas evaporated under reduced pressure. Theremaining triethyl phosphonoacetate was removed by distillationin vacuo. The crude product was purified bycolumn chromatography on silica gel using a diethyl ether:light petroleum (40-60) 1: 1 mixture as the eluent. Thewhite crystalline product was then recrystallized fromethanol/water by first dissolving the crude product inethanol and then adding water until the solution misted.For crystallization the solution was placed in the refrigerator.Yield: 50% (0.78 g, 3.08 mmol, for both syntheticprocedures); m.p.: 51-52 C; IR: v = 1711 vs, 1645 m,1582 m, 1547 m, 1458 w, 1400 w, 1365 w, 1323 w,1306 s, 1271 m, 1242 w, 1189 s, 1177vs, 1034 m, 997 s,845 s, 789 vs, 743 s, 600 m, 571 m, 492 m cm-1; MS(EI): m/z (%) = 254.1 (30) [M?], 225.2 (10) [M?-C2H5 ],210.2 (60) [M?-C2H4O], 182.4 (100) [M?-CO2C2H5 ,?H?]; 1H NMR (CDCl3, 600 MHz, 298 K): d = 1.34(CH3, 3H, t, J = 7.1 Hz), 4.28 (CH2, 2H, q, J = 7.1 Hz),6.72 (=CH, 1H, d, J = 15.9 Hz), 7.33 (=CHar, 1H, ddd,J = 1.1 Hz, 4.7 Hz, 7.7 Hz), 7.36 (=CHar, 1H, dd,J = 1.6 Hz, 4.9 Hz), 7.68 (=CH, 1H, d, J = 15.9 Hz),7.81 (=CHar, 1H, ddd, J = 1.9 Hz, 7.7 Hz, 8.1 Hz), 8.40(=CHar, 1H, d, J = 8.1 Hz), 8.53 (=CHar, 1H, s), 8.66-8.70(=CHar, 2H, m) ppm; 13C NMR (CDCl3, 150.92 MHz,298 K): d = 14.2 (CH3), 60.8 (CH2), 119.1 (=CHar), 121.1(=CHar), 121.7 (=CHar), 123.0 (=CH), 124.0 (=CHar),136.9 (=CHar), 141.8 (=CH), 142.6 (=Car), 149.2 (=CHar),149.8 (=CHar), 155.5 (=CH), 157.0 (=CH), 166.1 (C=O)ppm.
  • 13
  • [ 68-12-2 ]
  • [ 14162-95-9 ]
  • [ 146581-82-0 ]
YieldReaction ConditionsOperation in experiment
80% Compound 4 (1.8 g, 7.7 mmol) was dissolved in 20 cm3anhydrous diethyl ether and 20 cm3 anhydrous tolueneunder a nitrogen atmosphere at -78 C. Butyl lithium inhexane (4.0 cm3, 2.5 M) was added dropwise. The solutionwas stirred at -78 C for 90 min before 8.0 cm3 anhydrousdimethyl formamide were added. The resulting solutionwas then stirred for another 90 min at the same temperature.To stop the reaction 50 cm3 of 2 N hydrochloric acidwere added at -78 C and the solution was allowed toreach room temperature. The organic phase was separatedand the aqueous phase was neutralized with diluted sodiumhydroxide solution. A smooth white precipitate wasformed. The aqueous phase was extracted three times withCH2Cl2. The solvent was evaporated under reducedpressure and a light brown oil that solidified to a lightbrown solid was obtained. Yield: 80% (1.1 g, 6.16 mmol);m.p.: 85-56 C [18]; MS (EI): m/z (%) = 184.1 (80) [M?],185.0 (10) [M??H?], 156.2 (100) [M?-CO?].
  • 14
  • [ 33421-43-1 ]
  • [ 146581-82-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sulfuric acid; potassium nitrate / 2 h / 130 °C / Microwave irradiation; Cooling 2.1: acetic acid; Acetyl bromide / 2 h / 130 °C / Microwave irradiation 3.1: n-butyllithium / diethyl ether; toluene; hexane / 1.5 h / -78 °C / Inert atmosphere 3.2: 1.5 h / -78 °C / Inert atmosphere
  • 15
  • [ 14163-00-9 ]
  • [ 146581-82-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetic acid; Acetyl bromide / 2 h / 130 °C / Microwave irradiation 2.1: n-butyllithium / diethyl ether; toluene; hexane / 1.5 h / -78 °C / Inert atmosphere 2.2: 1.5 h / -78 °C / Inert atmosphere
  • 16
  • [ 366-18-7 ]
  • [ 146581-82-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / 24 h / 20 °C / Cooling with ice 2.1: sulfuric acid; potassium nitrate / 2 h / 130 °C / Microwave irradiation; Cooling 3.1: acetic acid; Acetyl bromide / 2 h / 130 °C / Microwave irradiation 4.1: n-butyllithium / diethyl ether; toluene; hexane / 1.5 h / -78 °C / Inert atmosphere 4.2: 1.5 h / -78 °C / Inert atmosphere
  • 17
  • [ 146581-82-0 ]
  • [ 105-53-3 ]
  • diethyl 2-(2,2'-bipyridin-4-ylmethylene)malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With piperidine; acetic acid In n-heptane for 17h; Reflux; 2.2 Synthesis of diethyl 2-(2,2'-bipyridin-4-ylmethylene)malonate (3) 0.5 cm3 (2.5 mmol) diethyl malonate, one drop of piperidine,one drop of acetic acid and 0.46 g (2.5 mmol) 2,2'-bipyridine-4-carbaldehyde17 were dissolved in 10 cm3 n-heptane. Thereaction mixture was heated to reflux for 17 h. After coolingto room temperature 10 cm3 distilled water and 10 cm3methyl tert-butyl ether were added. The organic layer wasseparated and washed with 10 cm3 water and 10 cm3 brine.The organic layer was dried over sodium sulfate and thesolvent was evaporated. The crude product was purified bycolumn chromatography using alumina as stationary phaseand a mixture of diethyl ether and toluene (1:2) as eluent. Theproduct was recrystallized from an ethanol water mixture bydissolving the product first in ethanol and adding water untilthe solution turned cloudy. Yield: 14% (0.12 g, 0.35 mmol).IR (298 K) [cm-1]: 2995w, 2970w, 2936w, 1715vs, 1697s,1643m, 1589m, 1547m, 1450m, 1364s, 1317s, 1206s, 1177vs,1028m, 982m, 839s; MS (EI), m/z (%): 327 (1) [MH+], 297(65) [M+- C2H5], 282 (62) [MH+- C2H5O], 269 (65) [M+-2 C2H5], 253 (80) [MH+- C2H5O - C2H5], 235 (30) [MH+-2 C2H5OH], 225 (100) [MH+- C3H5O2 - C2H5], 210 (100)[C13H10N2O+], 182 (95) [C10H9N+2 ], 156 (15) [C10H8N+2 ];1H-NMR (CDCl3): δ [ppm] = 1.32 (t, J= 7.07 Hz, 3 H), 1.36(t, J= 7.20 Hz, 3 H), 4.34 (q, J= 1.00 Hz, 2 H), 4.39 (q, J=1.00 Hz, 2 H), 7.31-7.36 (m, 2 H), 7.76 (s, 1 H), 7.83 (td, J=7.77, 1.89 Hz, 1 H), 8.40 (dt, J= 7.89, 0.98 Hz, 1 H), 8.48-8.51 (m, 1 H), 8.66-8.69 (m, 1 H), 8.71 (d, J= 5.31 Hz, 1H); 13C-NMR (CDCl3):δ [ppm] = 13.8, 14.1, 62.0, 120.6,121.0, 122.4, 124.0, 130.5, 136.9, 139.3, 141.3, 149.2, 149.7,155.3, 157.0, 163.4, 165.6; M.p.: 65-67 °C; elemental analysis:calc. (%) for C18H18N2O4: C 66.25, H 5.56, N 8.58;found: C 67.94, H 5.65, N 8.85.
  • 18
  • C24H52N8S6Sn4 [ No CAS ]
  • [ 146581-82-0 ]
  • C68H76N16S6Sn4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane at 20℃; for 48h; Inert atmosphere;
  • 19
  • [ 146581-82-0 ]
  • [ 7646-85-7 ]
  • C11H8Cl2N2OZn [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane for 48h; Inert atmosphere;
  • 20
  • C17H11N3S [ No CAS ]
  • [ 146581-82-0 ]
  • C28H17N5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
62.31% With piperidine In dichloromethane at 20℃;
  • 21
  • [ 146581-82-0 ]
  • C36H34N8O11ReS2(1+)*CF3O3S(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: ethanol / 3 h / Reflux; Inert atmosphere 1.2: 3 h / 20 °C / Cooling with ice 2.1: toluene / 4 h / Inert atmosphere; Reflux 3.1: 12 h / Inert atmosphere; Darkness; High pressure 4.1: tetrahydrofuran / 12 h / Reflux; Inert atmosphere
  • 22
  • [ 146581-82-0 ]
  • C24H24BrN4O5ReS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: ethanol / 3 h / Reflux; Inert atmosphere 1.2: 3 h / 20 °C / Cooling with ice 2.1: toluene / 4 h / Inert atmosphere; Reflux
  • 23
  • [ 146581-82-0 ]
  • C26H27N5O5ReS(1+)*CF3O3S(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: ethanol / 3 h / Reflux; Inert atmosphere 1.2: 3 h / 20 °C / Cooling with ice 2.1: toluene / 4 h / Inert atmosphere; Reflux 3.1: 12 h / Inert atmosphere; Darkness; High pressure
  • 24
  • [ 146581-82-0 ]
  • C30H32N6O5ReS(1+)*CF3O3S(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: ethanol / 3 h / Reflux; Inert atmosphere 1.2: 3 h / 20 °C / Cooling with ice 2.1: toluene / 4 h / Inert atmosphere; Reflux 3.1: 12 h / Inert atmosphere; Darkness; High pressure 4.1: tetrahydrofuran / 12 h / Reflux; Inert atmosphere 5.1: GLUTATHIONE / aq. phosphate buffer / 12 h / 24.84 °C / pH 7.4
  • 25
  • [ 146581-82-0 ]
  • C29H29N5O5ReS(1+)*CF3O3S(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: ethanol / 3 h / Reflux; Inert atmosphere 1.2: 3 h / 20 °C / Cooling with ice 2.1: toluene / 4 h / Inert atmosphere; Reflux 3.1: 12 h / Inert atmosphere; Darkness; High pressure 4.1: tetrahydrofuran / 12 h / Reflux; Inert atmosphere
  • 26
  • [ 14316-16-6 ]
  • [ 146581-82-0 ]
  • 4-N-((p-toluenesulfonylamino)ethyl)aminomethyl-4’-methyl-2,2’-bipyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: N-tosylethylenediamine; 2,2'-bipyridine-4-carboxaldehyde In ethanol for 3h; Reflux; Inert atmosphere; Stage #2: With sodium tetrahydroborate at 20℃; for 3h; Cooling with ice;
  • 30
  • [ 146581-82-0 ]
  • C29H32N6O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: methanol / 72 h / 20 °C 2: dichloromethane / 2.5 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 0 - 20 °C
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