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[ CAS No. 67491-43-4 ] {[proInfo.proName]}

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Chemical Structure| 67491-43-4
Chemical Structure| 67491-43-4
Structure of 67491-43-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 67491-43-4 ]

CAS No. :67491-43-4 MDL No. :MFCD06637688
Formula : C12H6N4 Boiling Point : -
Linear Structure Formula :- InChI Key :IUMFOUVCDJGKNS-UHFFFAOYSA-N
M.W : 206.20 Pubchem ID :10442958
Synonyms :

Calculated chemistry of [ 67491-43-4 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.9
TPSA : 73.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.83
Log Po/w (XLOGP3) : 0.92
Log Po/w (WLOGP) : 1.89
Log Po/w (MLOGP) : -0.4
Log Po/w (SILICOS-IT) : 2.41
Consensus Log Po/w : 1.33

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.19
Solubility : 1.34 mg/ml ; 0.0065 mol/l
Class : Soluble
Log S (Ali) : -2.05
Solubility : 1.85 mg/ml ; 0.00899 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.35
Solubility : 0.00925 mg/ml ; 0.0000449 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.09

Safety of [ 67491-43-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 67491-43-4 ]

* 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 [ 67491-43-4 ]

[ 67491-43-4 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 100137-02-8 ]
  • [ 67491-43-4 ]
YieldReaction ConditionsOperation in experiment
88% With trichlorophosphate for 61h; ultrasonication;
56.2% With pyridine; thionyl chloride at 100℃; for 16h;
With thionyl chloride In pyridine; dichloromethane 4 EXAMPLE 4: A suspension of 4.73 g (0.0195 mol) of 4,4'-dicarbamoyl-2,2'-bipyridine [J. Am. Chem. Soc. 80. 2745 (1958)] and 5.67 g (0.0476 mol) of thionyl chloride in 30 ml of pyridine is stirred for 16 hours at 100°. After cooling, the reaction mixture is diluted with 100 ml of methylene chloride, filtered and concentrated to dryness by evaporation. The residue is then chromatographed with methylene chloride over silica gel. In this manner, 4,4'-dicyano-2,2'-bipyridine is obtained in the form of white crystals having a melting point of 238°-240°.
  • 2
  • [ 67-56-1 ]
  • [ 67491-43-4 ]
  • [ 145276-27-3 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate for 5h; Heating;
  • 3
  • [ 108-89-4 ]
  • [ 67491-43-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Raney nickel 2: oxidation 4: ammonia 5: 88 percent / trichlorooxophosphorus / 61 h / ultrasonication
  • 4
  • [ 1134-35-6 ]
  • [ 67491-43-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: oxidation 3: ammonia 4: 88 percent / trichlorooxophosphorus / 61 h / ultrasonication
  • 5
  • [ 6813-38-3 ]
  • [ 67491-43-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: ammonia 3: 88 percent / trichlorooxophosphorus / 61 h / ultrasonication
  • 6
  • [ 72460-28-7 ]
  • [ 67491-43-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonia 2: 88 percent / trichlorooxophosphorus / 61 h / ultrasonication
  • 7
  • [ 67491-43-4 ]
  • C12H12N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: MeONa / 5 h / Heating 2: NH4Cl, NH3 / methanol; ethanol / 1 h / 70 °C
  • 8
  • methanolic ammonia [ No CAS ]
  • [ 67491-43-4 ]
  • CGP 46430A [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium chloride; sodium methylate In hydrogenchloride; methanol; acetic acid 4 EXAMPLE 4: EXAMPLE 4: 4,4'-diamidino-2,2'-bipyridine dihydrochloride 0.5 m of 1.1N sodium methoxide in absolute methanol is added to a suspension of 1.2 g (0.0058 mol) of 4,4'-dicyano-2,2'-bipyridine in 48 ml of absolute methanol and the whole is boiled for 5 hours under reflux. 0.05 M of glacial acetic acid, 0.72 g (0.0134 mol) of ammonium chloride and 10 ml of 4.6N methanolic ammonia solution are then added to the solution while it is still warm and the whole is boiled for a further one hour. The cooled reaction mixture is concentrated by evaporation, taken up in 60 ml of 0.1N hydrochloric acid, filtered and applied to a column of 250 ml of Amberlite ER 180 adsorber resin. Washing is effected with distilled water and 5 ml fractions are collected. Fractions 14-21 are combined and concentrated by evaporation and the residue is crystallized from a small amount of water to give the title compound; m.p. >280°. The starting compound is prepared as follows:
  • 9
  • {Mo(CO)4(η2,η2-bicyclo{2.2.1.}hepta-2,4-diene)} [ No CAS ]
  • [ 67491-43-4 ]
  • [ 118982-97-1 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran under nitrogen;; removal of solvent under vacuum; washing (CHCl3); drying (vacuum); recrystd. (CH2Cl2/ light petroleum); elem. anal.;;
  • 10
  • [ 12146-36-0 ]
  • [ 67491-43-4 ]
  • [ 163364-90-7 ]
YieldReaction ConditionsOperation in experiment
65% In tetrahydrofuran according to Baxter et al., J. Chem. Soc. Dalton Trans. (1992), 3015; slight excess of norbornadiene complex; elem. anal.;
  • 11
  • [ 12129-25-8 ]
  • [ 67491-43-4 ]
  • [ 163364-91-8 ]
YieldReaction ConditionsOperation in experiment
90% In tetrahydrofuran according to Baxter et al., J. Chem. Soc. Dalton Trans. (1992), 3015; slight excess of norbornadiene complex; elem. anal.;
  • 12
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 479081-39-5 ]
  • [ 67491-43-4 ]
  • [(4,4'-di-tert-butyl-2,2'-bipyridine)2Ru(4,4'-dicyano-2,2'-bipyridine)](PF6)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With silver nitrate In N,N-dimethyl-formamide other Radiation; Ru complex, ligand and AgNO3 dissolved in DMF, refluxed under microwavesfor 2 h; cooled to room temp., filtered, evapd., EtOH added, pptd. (aq. NH4PF6), sepd., washed (Et2O), dried (vac.), chromd. (silica, MeCN), crystd. fromMeOH/H2O;
  • 13
  • [ 100-48-1 ]
  • [ 67491-43-4 ]
YieldReaction ConditionsOperation in experiment
20% With palladium 10% on activated carbon for 24h; Inert atmosphere; Reflux;
7 %Spectr. With 1,10-Phenanthroline; silver(I) acetate; palladium diacetate; Trimethylacetic acid In toluene at 140℃; for 18h; Inert atmosphere; 4 Under a nitrogen atmosphere, palladium acetate (11.2 mg, 0.05mmol), 1, 10 - phenanthroline (49.6 mg, 0.25mmol), silver acetate (250 mg, 1.5mmol), (1 ml) was suspended in pyridine (51.1 mg, 0.5mmol) pivalic acid, stirred at 140 °C 26 hours. After the reaction mixture was cooled to room temperature, the insoluble matter was removed by filtration over celite, methylene chloride (10 ml) was washed. The filtrate was concentrated under reduced pressure, 1, 1, 2, 2 - tetrachloroethane (15.8 μl, 0.15mmol) was added as an internal standard substance was obtained residue,1H NMR (88%) yield was calculated based oxidizing agent. (Methylene chloride/hexane=5/95) to give a residue for a thin layer chromatography analysis, the subject compound (quantitative value NMR 89%, 80% isolated yield) was obtained as a white powder 93.1 mg.The same treatment as in Example 1-1 was carried out except that treatment was carried out under the conditions shown in Table 4 below.The results are shown in Table 4.
  • 14
  • [ 75-77-4 ]
  • [ 67491-43-4 ]
  • [ 4039-32-1 ]
  • C30H60N6Si6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,2’-bipyridine-4,4’-dicarbonitrile; lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 96h; Stage #2: chloro-trimethyl-silane In toluene for 12h; Reflux;
  • 15
  • [ 773837-37-9 ]
  • [ 18511-71-2 ]
  • [ 67491-43-4 ]
YieldReaction ConditionsOperation in experiment
63% With N,N,N,N,-tetramethylethylenediamine; 1,5-bis-(diphenylphosphino)pentane; palladium diacetate In 1,3,5-trimethyl-benzene for 12h; Inert atmosphere; Reflux;
45% With N,N,N,N,-tetramethylethylenediamine; 1,5-bis-(diphenylphosphino)pentane; palladium diacetate In 1,3,5-trimethyl-benzene at 170℃; for 17h; Inert atmosphere;
  • 16
  • [ 780722-26-1 ]
  • [ 67491-43-4 ]
  • [ 1268344-20-2 ]
YieldReaction ConditionsOperation in experiment
85% With potassium hydroxide In ethyl methyl ether for 12h; Reflux;
  • 17
  • [ 14099-01-5 ]
  • [ 108-88-3 ]
  • [ 67491-43-4 ]
  • fac-ReICl(CO)3(4,4′-dicyano-2,2′-bipyridyl) [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In chloroform for 7h; Inert atmosphere; Darkness; Reflux;
  • 18
  • [Ir(2-(benzo[b]thiophen-2-yl)-pyridine)2(triphenylphosphine)2μ-Cl]2 [ No CAS ]
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 67491-43-4 ]
  • [Ir(btp)2(bpy-CN)]+PF6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: [Ir(2-(benzo[b]thiophen-2-yl)-pyridine)2(triphenylphosphine)2μ-Cl]2; 2,2’-bipyridine-4,4’-dicarbonitrile In ethylene glycol at 150℃; for 45h; Inert atmosphere; Stage #2: ammonium hexafluorophosphate Inert atmosphere;
  • 19
  • [Ir(2-(benzo[b]thiophen-2-yl)-pyridine)2(triphenylphosphine)2μ-Cl]2 [ No CAS ]
  • [ 67491-43-4 ]
  • [Ir(btp)2(bpy-CN)]+PF6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In ethylene glycol at 150℃; for 45h; Inert atmosphere; 2-1 2-1: Synthesis of [Ir(btp)2(bpy-CN)2]PF5 (IrCN ) A mixture of Ir-dimer complex (0.088 g, 0.068mmol) and 4,4’-dicyano-2,2’-bipyridine (bpy-CN: 0.029 g, 0.14 mmol) in ethylene glycol (5.9 mL) was heated at 1500 C. for 45 h under nitrogen. The reaction mixture was poured into water (40 mL) and washed with diethyl ether (40 mLx2). To the aqueous layer was added ammonium hexafluorophosphate (0.610 g, 3.74 mmol). The organic mixture products were extracted with dichloromethane (40 mLx2) and the solvent was removed by rotary evaporation under vacuum. The solids were collected by filtration, washed with water and vacuum dried. The obtained crude product was purified by column chromatography on silica gel (solvent: methanol/dichloromethane, 1:6 v/v), followed by recrystallization from dichloromethane through n-hexane vapor diffusion to yield complex Ir-CN as dark-green crystals (0.056 g, 0.058 mmol, 85% yield). ‘H NMR (300 MHz, DMSO-d5) ö 9.54 (s, 2H),8.13 (d, J=7.2 Hz, 2H), 8.xx8.Ox (m, 4H), 7.95 (m, 4H), 7.77 (d, J=5.7 Hz, 2H), 7.23 (t, J=7.5 Hz, 2H), 7.08 (t, J=6.9 Hz, 2H), 6.88 (t, J=8.0 Hz, 2H), 5.86 (d, J=8.1 Hz, 2H). ‘3C NMR (100.6 MHz, DMSO-d5) ö 163.17, 155. 69, 151.87, 150.89, 145.64, 144.61, 142.10, 140.69, 136.47,132.10, 128.63, 125.84, 124.49, 124.15, 123.57, 122.67,122.21, 119.99, 115.65. ESI-MS calcd. for C44H35F5IrN5PS2, 819.0977 [M-PF5 found 819 [M-P F5.
  • 20
  • [ 14364-93-3 ]
  • [ 67491-43-4 ]
  • [PtMe3(4,4'-dicyano-2,2'-bipyridine)I] [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% In chloroform at 20℃; for 1.5h;
  • 21
  • [Ru(1,10-phenanthroline)2Cl2] [ No CAS ]
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 67491-43-4 ]
  • (2,2’-bipyridine-4,4’-carboxamide)bis(1,10-phenanthroline)ruthenium(II)hexafluorophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% Stage #1: [Ru(1,10-phenanthroline)2Cl2]; 2,2’-bipyridine-4,4’-dicarbonitrile With water In ethanol for 18h; Reflux; Inert atmosphere; Stage #2: ammonium hexafluorophosphate In water
  • 22
  • [ 72905-30-7 ]
  • [ 67491-43-4 ]
  • [Ru(2,2’:6’,2’’-terpyridine)(4,4'-dicyano-2,2'-dipyridyl)Cl]Cl [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; lithium chloride In ethylene glycol at 180℃; for 1h;
  • 23
  • [Ru(1,10-phenanthroline)2Cl2] [ No CAS ]
  • ammonium hexafluorophosphate [ No CAS ]
  • [ 67491-43-4 ]
  • (2,2’-bipyridine-4,4’-carboxamide)bis(1,10-phenanthroline)ruthenium(II) hexafluorophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% Stage #1: [Ru(1,10-phenanthroline)2Cl2]; 2,2’-bipyridine-4,4’-dicarbonitrile With water In ethanol for 18h; Inert atmosphere; Reflux; Stage #2: ammonium hexafluorophosphate With water (2,2'-bipyridine-4,4'-carboxamide)bis(1,10-phenanthroline)ruthenium(II) hexafluorophosphate [Ru(CONH2-bpy)(phen)2](PF6)2 (4) (Comparative) RuCl2(phen)2 (150 mg, 0.28 mmol, 1.0 equiv.) and 2,2'-Bipyridine-4,4'-dicarbonitrile (64 mg, 0.31 mmol, 1.1 equiv.) were dissolved in a 1:1 mixture of H2O/EtOH (30 mL) and were refluxed for 18 h under N2 atmosphere. The solvent was evaporated and the residue redissolved in 5 mL of H2O. A saturated, aq. NH4PF6 solution was added and the resulting precipitate was collected by vacuum filtration. The solid was washed with H2O (50 mL) and Et2O (50 mL). The product was purified by column chromatography on silica gel with an CH3CN /aq. KNO3 (0.4 M) solution (10:1). The fractions containing the product were united and the solvent was removed. The residue was dissolved in CH3CN and undissolved KNO3 was removed by filtration. The solvent was removed again and the product was dissolved in H2O (50 mL). Upon addition of NH4PF6 the product precipitated as a PF6 salt. The solid was obtained by filtration and was washed with H2O (50 mL) and Et2O (50 mL). The product was dried in high vacuum. Yield: 16%. 1H NMR (400 MHz, CD3CN) δ = 8.97 (2H, s), 8.67 (2H, d, 3J = 8.3 Hz), 8.58 (2H, d, 3J = 8.3 Hz), 8.30-8.22 (4H, m), 8.18 (2H, d, 3J = 5.2 Hz), 7.87-7.84 (4H, m), 7.79 (2H, dd, 3J = 8.3 Hz, 3J = 5.2 Hz), 7.61-.7.57 (4H, m), 7.25 (2H, s), 6.48 (2H, s). 13C NMR (100 MHz, CD3CN) δ = 165.7, 158.8, 154.0, 153.9, 153.5, 148.6, 148.3, 143.0, 138.2, 138.0, 132.1, 132.0, 129.1, 129.0, 127.0, 127.0, 126.0, 123.1. HR-MS (ESI + m/z): Calcd. [M-2PF 6] 2+ : 352.06056; found: 352.06063. EA (%): Calcd. for (C36H26F12N8O2P2Ru): C 43.52, H 2.64, N 11.28; found. C 43.33, H 2.47, N 11.15.
  • 24
  • [ 14099-01-5 ]
  • [ 67491-43-4 ]
  • [Re(4,4′-dicyano-2,2′-bipyridine)Cl(CO)3] [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% In toluene for 3h; Reflux;
  • 25
  • [ 67491-43-4 ]
  • [Re(4,4′-dicyano-2,2′-bipyridine)(H2O)(CO)3] [trifluoromethanesulfonate] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 3 h / Reflux 2: acetone / 4 h / Reflux; Darkness
  • 26
  • [ 17084-13-8 ]
  • [bis[2-(benzo[b]thiophen-2-yl)quinoline]iridium(III)(μ-Cl)]2 [ No CAS ]
  • [ 67491-43-4 ]
  • C46H26IrN6S2(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: [bis[2-(benzo[b]thiophen-2-yl)quinoline]iridium(III)(μ-Cl)]2; 2,2’-bipyridine-4,4’-dicarbonitrile In methanol; dichloromethane at 70℃; for 24h; Inert atmosphere; Stage #2: potassium hexafluorophosphate In methanol; dichloromethane at 20℃; for 2h; 1 Weigh 101.6 mg of the ligand with the structure shown in formula III and 43.3 mg of 4,4'-dicyano-2,2'-bipyridine, dissolve them in a mixed solvent of 30mL CH3OH and 30mL CH2Cl2, and condense and reflux at 70°C under nitrogen protection React for 24 hours, add 0.8 mmol potassium hexafluorophosphate to the resulting chloride ion-containing iridium complex system, stir at room temperature for 2 hours, collect the filtrate by suction under reduced pressure, and carry out column chromatography separation to obtain the structure of formula I containing dicyanide Base iridium complex [(btpq)2-Ir-bpy-2CN)][PF6].
  • 27
  • C2F6NO4S2(1-)*C6H12Au(1+) [ No CAS ]
  • [ 67491-43-4 ]
  • [(κ2-4,4'-(dicarbonitrile)bipy)-(η2-ethylene)gold(I)][NTf2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% In dichloromethane at 18 - 25℃; for 1h;
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