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CAS No. : | 49669-22-9 | MDL No. : | MFCD00234587 |
Formula : | C10H6Br2N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WZVWSOXTTOJQQQ-UHFFFAOYSA-N |
M.W : | 313.98 | Pubchem ID : | 4407547 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 62.87 |
TPSA : | 25.78 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.71 cm/s |
Log Po/w (iLOGP) : | 2.8 |
Log Po/w (XLOGP3) : | 3.53 |
Log Po/w (WLOGP) : | 3.67 |
Log Po/w (MLOGP) : | 2.29 |
Log Po/w (SILICOS-IT) : | 3.8 |
Consensus Log Po/w : | 3.22 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.58 |
Solubility : | 0.00828 mg/ml ; 0.0000264 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.76 |
Solubility : | 0.0551 mg/ml ; 0.000176 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.86 |
Solubility : | 0.000437 mg/ml ; 0.00000139 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.19 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-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 |
---|---|---|
79% | Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 2 h; Stage #2: at -78℃; for 1 h; Stage #3: With oxygen In diethyl ether; hexane at -78 - 20℃; for 2 h; |
Example 42 6,6'-dibromo-2,2'-bipyridine 52b In a three-necked round-bottomed flask, the 2,6-dibromopyridine (42) (2.32 g, 10 mmol) is solubilized in 250 ml of diethyl ether cooled to -78° C. The assembly is equipped with a solids-addition funnel containing copper chloride (2) (pre-dried, 2 g, 14.9 mmol). Butyllithium (2.4M in hexane, 4.6 ml, 11 mmol) is added dropwise and the reaction medium is stirred for 2 hours at -78° C. The copper chloride is added slowly over 30 minutes and the mixture is stirred for a further 30 minutes at -78° C. Dry oxygen bubbling is carried out for 1 hour at -78° C. and then for 1 hour at ambient temperature. The reaction medium is treated with 200 ml of water and 50 ml of a 1M solution of HCl, and a precipitate appears. The solution is filtered and the resulting solid is recrystallized from THF. The brownish solid is subsequently solubilized in THF and filtered through a Millipore filter. The solution is concentrated under vacuum and the desired product is obtained in the form of a white powder with a yield of 79percent. 1H NMR (CDCl3) δ(ppm): 7.50 (dd, J=0.6, 8.1, 2H, Hpyridine), 7.66 (t, J=7.8, 2H, Hpyridine), 8.37 (dd, J=0.6, 8.4, 2H, Hpyridine). 13C NMR (CDCl3) δ (ppm): 119.71, 128.15, 138.86, 141.15, 155.16. MS, m/z (I percent): 314 (M++2, 100percent), 312 (M+, 45percent), 233 (M+-Hr, 54percent), 153 (M+-2Br, 32percent). |
30% | Stage #1: With n-butyllithium In diethyl ether at -78℃; for 0.5 h; Stage #2: With oxygen; copper dichloride In diethyl ether at -78 - -50℃; |
The 7.15 g 2,6-dibromopyridine was stirred and dissolved in100 ml diethyl ether under room temperature, followed by addition of 15 ml (2.5 mol/L) n-BuLi drop by drop under -78 °C. Afterthe mixture was stirred under -78 °C for 0.5 h, the temperatureraised naturally to 50 C by stopping cooling, and then decreasedto -78 °C by restarting cooling, followed by adding 4.12 g CuCl2into the mixture. The resulting mixture was transferred into theoxygen atmosphere for 30 min, when reaching to -50 to -60 °C.The reaction was quenched by the addition of a few drops of water,and the liquid phase of the mixture was obtained by suction filtration,dried over Na2SO4, filtered, and evaporated under reducedpressure. After purifying by column chromatography on silica gel,6,6'-dibromo-2,2'-bipyridine was obtained in 30percent yield. 1H NMRin Fig. S1 (400 MHz, CDCl3, TMS) δ 7.50 (2H), 7.65 (2H), 8.37 (2H)ppm; 13C NMR in Fig. S1 (CDCl3, 100 MHz) δ 120.17, 128.60,139.31, 141.6, 155.62 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With bis(bipyridine)nickel(II) bromide; sodium iodide In N,N-dimethyl-formamide at 20℃; for 3.3 h; Electrochemical reaction; Inert atmosphere | General procedure: To an undivided electrochemical cell, fitted by a zinc rod as the anode and surrounded by a nickel foam as the cathode, were added DMF (50 mL), 0.1 M NaI, and 1,2-dibromoethane (2.5 mmol, 215 μL). The mixture was electrolyzed under argon at a constant current intensity of 0.2 A at room temperature for 15-20 min. Then the current was stopped, and [Ni(bpy)]Br2 complex21 (1 mmol, 375 mg), 2,6-dichloropyridine (10 mmol, 1.48 g) or 2,6-dibromopyridine (10 mmol, 2.38 g) were sequentially added. The solution was electrolyzed at 0.1 A and room temperature until the starting material was totally consumed (3.3 h). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | at 95℃; | With the aim of improving the preparation of 6,6'-dihalo-2,2'-bipyridines, a different synthesis strategy was envisioned. This synthesis is made up of three steps starting from the 2-chloro-6-methoxypyridine 57; homocoupling of the 2-chloro-6-methoxypyridine 57, followed by hydrolysis of the 6,6'-methoxy groups of the dimer 58, then halogenation of the bipyridinone 59 obtained (Scheme 26). The 2-chloro-6-methoxypyridine 57 is homocoupled in the presence of a stoichiometric amount of a solution (1:0.3:1) of zinc, NiBr2(PPh3)2 and nBu4NI, in DMF at 55° C., so as to give the 6,6'-methoxy-2,2'-bipyridine 58 with a yield of 94percent. The hydrolysis of the 6,6'-methoxy groups is carried out with a mixture of 33percent of hydrobromic acid in acetic acid, at 95° C. for 48 h, with a yield of 94percent. The bipyridinone 59 treated with an excess of phosphorus oxychloride or of phosphorus oxybromide at 95° C., gives, respectively, the 6,6'-dichloro-2,2'-bipyridine 52a and the 6,6'-dibromo-2,2'-bipyridine 52b with virtually quantitative yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23 %Chromat. | With bis(bipyridine)nickel(II) bromide; sodium iodide In N,N-dimethyl-formamide at 20℃; Electrochemical reaction; Inert atmosphere | General procedure: The controlled current preparative electrolysis were carried out with a potentiostat/galvanostat equipment. Undivided cells with 20 mL compartment were used. Zn or Fe metallic rod with 8 mm diameter was used as the sacrificial anode. Ni foam (6 cm.x.3.5 cm) was used as the cathode. It could be re-used after washing with a 6 M HCl solution following by water and acetone, and dried. The same solution was used to clean the anode. A 5 mL DMF solution containing 7percent or 20percent of NiBr2*xH2O or [Ni(bpy)]Br221 and x mmol of the corresponding mixture of 2-bromomethylpyridines or 2,6-dihalopyridines (heterocouplings in Table 1, Table 2, Table 4 and Table 5), or (2.5 mmol) of 2,6-dihalopyridines (homocoupling in Table 3) was stirred or sonicated before the electrolysis, to ensure the solubilization of reagents. A pre-electrolysis was carried out with 15 mL of the electrolytic solution (DMF, 0.1 M NaI and 0.75 mmol of 1,2-dibromoethane), passing a charge of 146 C (I=150 mA). Then, the previous prepared solution of bromopicoline or bromopyridine and the catalyst in 5 mL DMF, was added to the electrolytic cell and the constant current electrolysis (I=100 mA) applied. It is important to ensure that the cell potential must not exceed 1.8 V in order to avoid the reduction of the substrate on the cathode surface. After the total consumption of the reagent (number of coulombs described in the tables), the reaction was stopped and the solvent removed under reduced pressure. The residue was dissolved in CH2Cl2 and washed with several portions of a 6 M NH4OH solution. After drying over Na2SO4, the organic layer was evaporated under reduced pressure. |
7 %Chromat. | With bis(bipyridine)nickel(II) bromide; sodium iodide In N,N-dimethyl-formamide at 20℃; Electrochemical reaction; Inert atmosphere | General procedure: The controlled current preparative electrolysis were carried out with a potentiostat/galvanostat equipment. Undivided cells with 20 mL compartment were used. Zn or Fe metallic rod with 8 mm diameter was used as the sacrificial anode. Ni foam (6 cm.x.3.5 cm) was used as the cathode. It could be re-used after washing with a 6 M HCl solution following by water and acetone, and dried. The same solution was used to clean the anode. A 5 mL DMF solution containing 7percent or 20percent of NiBr2*xH2O or [Ni(bpy)]Br221 and x mmol of the corresponding mixture of 2-bromomethylpyridines or 2,6-dihalopyridines (heterocouplings in Table 1, Table 2, Table 4 and Table 5), or (2.5 mmol) of 2,6-dihalopyridines (homocoupling in Table 3) was stirred or sonicated before the electrolysis, to ensure the solubilization of reagents. A pre-electrolysis was carried out with 15 mL of the electrolytic solution (DMF, 0.1 M NaI and 0.75 mmol of 1,2-dibromoethane), passing a charge of 146 C (I=150 mA). Then, the previous prepared solution of bromopicoline or bromopyridine and the catalyst in 5 mL DMF, was added to the electrolytic cell and the constant current electrolysis (I=100 mA) applied. It is important to ensure that the cell potential must not exceed 1.8 V in order to avoid the reduction of the substrate on the cathode surface. After the total consumption of the reagent (number of coulombs described in the tables), the reaction was stopped and the solvent removed under reduced pressure. The residue was dissolved in CH2Cl2 and washed with several portions of a 6 M NH4OH solution. After drying over Na2SO4, the organic layer was evaporated under reduced pressure. |