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Product Details of [ 366-18-7 ]

CAS No. :366-18-7 MDL No. :MFCD00006212
Formula : C10H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :ROFVEXUMMXZLPA-UHFFFAOYSA-N
M.W : 156.18 Pubchem ID :1474
Synonyms :

Calculated chemistry of [ 366-18-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
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 : 47.47
TPSA : 25.78 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 : No
Log Kp (skin permeation) : -6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 1.5
Log Po/w (WLOGP) : 2.14
Log Po/w (MLOGP) : 0.91
Log Po/w (SILICOS-IT) : 2.55
Consensus Log Po/w : 1.81

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.43
Solubility : 0.584 mg/ml ; 0.00374 mol/l
Class : Soluble
Log S (Ali) : -1.65
Solubility : 3.5 mg/ml ; 0.0224 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -4.16
Solubility : 0.0109 mg/ml ; 0.00007 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 366-18-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P264-P270-P280-P301+P310-P302+P352+P312-P361+P364 UN#:2811
Hazard Statements:H301+H311 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 366-18-7 ]

* 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.

  • Upstream synthesis route of [ 366-18-7 ]
  • Downstream synthetic route of [ 366-18-7 ]

[ 366-18-7 ] Synthesis Path-Upstream   1~44

  • 1
  • [ 366-18-7 ]
  • [ 4392-87-4 ]
Reference: [1] Acta Chemica Scandinavica, 1998, vol. 52, # 1, p. 77 - 85
[2] Journal of the Chemical Society, 1938, p. 1662,1669
  • 2
  • [ 366-18-7 ]
  • [ 531-67-9 ]
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 4, p. 513 - 517
[2] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1985, p. 895 - 898
  • 3
  • [ 109-09-1 ]
  • [ 67-64-1 ]
  • [ 110-86-1 ]
  • [ 6302-02-9 ]
  • [ 366-18-7 ]
Reference: [1] Tetrahedron, 1993, vol. 49, # 21, p. 4495 - 4502
  • 4
  • [ 694-59-7 ]
  • [ 110-86-1 ]
  • [ 142-08-5 ]
  • [ 2739-97-1 ]
  • [ 366-18-7 ]
  • [ 109-97-7 ]
Reference: [1] Heterocycles, 1990, vol. 31, # 5, p. 783 - 786
  • 5
  • [ 366-18-7 ]
  • [ 5470-22-4 ]
Reference: [1] Yakugaku Zasshi, 1955, vol. 75, p. 733,735[2] Chem.Abstr., 1956, p. 3436
  • 6
  • [ 366-18-7 ]
  • [ 15862-19-8 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: at 100℃; for 24 h;
Stage #2: With sodium hydroxide In water
The procedure is similar to the preparation of 2. Mixture of 2,2'-bipyridine (0.5 g, 3.2 mmol), KBr (0.46 g, 3.87 mmol), and a mixed acid (3.9 ml of concentrated HNO3 and 7.7 ml of concentrated H2SO4) was allowed to react for 24 h under reflux after the temperature ascending to 100 °C rapidly. The reaction mixture was poured into 50 ml water and neutralized with solid sodium hydroxide until pH=7. The precipitate was filtered and washed with CHCl3, then extracted with CHCl3. The filtrate was dried over anhydrous MgSO4, the solvent was removed by rotary evaporation, and the residue was purified by column chromatography (EtOAc/petroleum ether, 1:5) to give desired product 5 (0.34 g, 45percent) as a white solid; mp 74-75 °C; Rf 0.40 (silica gel, EtOAc/petroleum ether, 1:3); [found: C, 51.11; H, 2.94. C10H7BrN2 requires C, 51.09; H, 3.00percent]; 1H NMR (400 MHz, CDCl3, ppm) δ 8.74-8.743 (d, J=2 Hz, 1H), 8.70-8.69 (d, J=4 Hz, 1H), 8.40-8.38 (d, J=8 Hz, 1H), 8.35-8.33 (d, J=8 Hz, 1H), 7.97-7.95 (d, J=8 Hz 1H), 7.86-7.82 (t, J=8 Hz, 1H), 7.36-7.33 (t, J=8 Hz, 1H); 13C NMR (100 MHz, CDCl3, ppm) δ 155.13, 154.59, 150.17, 149.23, 139.47, 137.00, 123.99, 122.33, 121.14. GC-MS (m/z) calcd for C10H7BrN2+ [M]+, found 233.95. The compound is known and that the data obtained matches that of the literature values.24b
Reference: [1] Tetrahedron, 2011, vol. 67, # 10, p. 1977 - 1982
  • 7
  • [ 26437-48-9 ]
  • [ 366-18-7 ]
  • [ 15862-19-8 ]
  • [ 61864-97-9 ]
Reference: [1] Phosphorus, Sulfur and Silicon and Related Elements, 1996, vol. 109, # 1-4, p. 605 - 608
  • 8
  • [ 26437-48-9 ]
  • [ 366-18-7 ]
  • [ 15862-19-8 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 23, p. 4077 - 4080
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 94, # 1-4, p. 405 - 410
  • 9
  • [ 26437-49-0 ]
  • [ 366-18-7 ]
  • [ 15862-19-8 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 23, p. 4077 - 4080
  • 10
  • [ 67-56-1 ]
  • [ 26437-48-9 ]
  • [ 366-18-7 ]
  • [ 15862-19-8 ]
Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 94, # 1-4, p. 405 - 410
  • 11
  • [ 67-56-1 ]
  • [ 26437-48-9 ]
  • [ 366-18-7 ]
  • [ 15862-19-8 ]
  • [ 61864-97-9 ]
Reference: [1] Phosphorus, Sulfur and Silicon and Related Elements, 1996, vol. 109, # 1-4, p. 605 - 608
[2] Phosphorus, Sulfur and Silicon and Related Elements, 1996, vol. 109, # 1-4, p. 605 - 608
  • 12
  • [ 366-18-7 ]
  • [ 178039-84-4 ]
Reference: [1] Journal of the Chemical Society, 1938, p. 1662,1669
[2] Organic Letters, 2015, vol. 17, # 6, p. 1497 - 1500
[3] Organometallics, 2016, vol. 35, # 15, p. 2429 - 2432
  • 13
  • [ 366-18-7 ]
  • [ 10495-73-5 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 39, p. 6941 - 6943
[2] Acta Chemica Scandinavica, 1998, vol. 52, # 1, p. 77 - 85
[3] Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 1037 - 1047
  • 14
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  • [ 10495-73-5 ]
  • [ 49669-22-9 ]
Reference: [1] Journal of the Chemical Society, 1938, p. 1662,1669
  • 15
  • [ 366-18-7 ]
  • [ 15862-18-7 ]
YieldReaction ConditionsOperation in experiment
86% at 150℃; for 15 h; 2,2′-bipyridine (1, 4.99 g, 0.032 mol) and bromine (10.24 g,0.064 mol) were first added in a hydrothermal reaction container andheated to 150 °C and annealed for 15 h. Then, the mixture was cooledand the hard solidwas powdered and following treatedwith Na2SO3 solutionto remove the unreacted bromine. Finally itwas basifiedwith sodiumhydroxide and filtered. The white solid product 5,5′-dibromo-2,2′-bipyridine was obtained by the chromatography on silica(CH2Cl2). 5,5′-dibromo-2,2′-bipyrimidine, 8.64 g (86percent). m.p. 221.6–222.1 °C. 1H-NMR (400 MHz, CDCl3, δ): 7.95 (d, 2H), 8.28 (s, 2H),8.71(d, 2H); 13C-NMR (100 MHz, CDCl3, δ): 121.47 (C5), 122.25 (C3),139.64 (C4); 150.28 (C6),153.64 (C2); IR (KBr): 3049 (C\\H,stretching), 1562, 1453, 1356 (Ar, stretching), 636 (C\\Br, stretching).Anal. calcd for C10H6N2Br2: C 38.22, H 1.91, N 8.92, Br 50.95; found: C38.26, H 1.94, N 8.90, Br 50.97.
86% at 150℃; for 15 h; 2,2'-bipyridyl (4.99 g, 0.032 mol) and liquid bromine (10.24 g, 0.064 mol)Put into a reaction kettle at a pressure of 2.0 atm at 150 ° C for 15 hours, then cool to room temperature after the reaction, pulverize the solid, add to the Na2SO3 solution and stir to remove unreacted bromine, filter, and alkalizate the acid with a 5percent NaOH solution. , filtration, to obtain a crude product, column separation with ethyl acetate / petroleum ether,8.64 g of white 5,5'-dibromo-2,2'-bipyridine was obtained in a yield of 91percent.
Reference: [1] Reactive and Functional Polymers, 2016, vol. 106, p. 93 - 98
[2] Patent: CN105130885, 2018, B, . Location in patent: Paragraph 0024; 0026; 0027; 0030; 0033; 0036
[3] New Journal of Chemistry, 2018, vol. 42, # 17, p. 14067 - 14070
[4] Chemistry - A European Journal, 2015, vol. 21, # 51, p. 18576 - 18579
[5] Patent: WO2009/118742, 2009, A1,
  • 16
  • [ 366-18-7 ]
  • [ 18511-69-8 ]
Reference: [1] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009, vol. 72, # 5, p. 1117 - 1121
[2] Synlett, 2011, # 2, p. 223 - 226
[3] Journal of Organometallic Chemistry, 2015, vol. 791, p. 175 - 182
[4] European Journal of Inorganic Chemistry, 2016, vol. 2016, # 10, p. 1470 - 1479
[5] Patent: CN104478922, 2017, B,
  • 17
  • [ 626-05-1 ]
  • [ 110-86-1 ]
  • [ 366-18-7 ]
  • [ 49669-22-9 ]
YieldReaction ConditionsOperation 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.
Reference: [1] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
[2] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
  • 18
  • [ 366-18-7 ]
  • [ 10495-73-5 ]
  • [ 49669-22-9 ]
Reference: [1] Journal of the Chemical Society, 1938, p. 1662,1669
  • 19
  • [ 366-18-7 ]
  • [ 18511-71-2 ]
Reference: [1] Chemistry Letters, 1994, # 7, p. 1267 - 1270
[2] Journal of the American Chemical Society, 2002, vol. 124, # 47, p. 14162 - 14172
[3] Synlett, 2011, # 2, p. 223 - 226
[4] Inorganic Chemistry, 2011, vol. 50, # 8, p. 3271 - 3280
[5] Patent: US2012/247546, 2012, A1,
[6] European Journal of Inorganic Chemistry, 2016, vol. 2016, # 10, p. 1470 - 1479
[7] Journal of Chemical Sciences, 2018, vol. 130, # 6,
  • 20
  • [ 366-18-7 ]
  • [ 3248-05-3 ]
Reference: [1] Dalton Transactions, 2005, # 9, p. 1644 - 1648
  • 21
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  • [ 4411-83-0 ]
Reference: [1] Helvetica Chimica Acta, 1993, vol. 76, # 2, p. 893 - 899
[2] Journal of the Chemical Society, 1938, p. 1662,1669
[3] European Journal of Inorganic Chemistry, 2014, vol. 2014, # 34, p. 5838 - 5848
[4] New Journal of Chemistry, 2016, vol. 40, # 7, p. 6374 - 6383
[5] RSC Advances, 2016, vol. 6, # 73, p. 69647 - 69657
[6] Inorganic Chemistry, 2018, vol. 57, # 19, p. 12255 - 12269
  • 22
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  • [ 151-50-8 ]
  • [ 4411-83-0 ]
Reference: [1] Dalton Transactions, 2006, vol. 6, # 13, p. 1645 - 1653
  • 23
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  • [ 17217-57-1 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 1, p. 315 - 319
[2] Advanced Synthesis and Catalysis, 2003, vol. 345, # 4, p. 497 - 505
  • 24
  • [ 366-18-7 ]
  • [ 18511-72-3 ]
Reference: [1] Yakugaku Zasshi, 1955, vol. 75, p. 733,735[2] Chem.Abstr., 1956, p. 3436
[3] Advanced Synthesis and Catalysis, 2003, vol. 345, # 4, p. 497 - 505
[4] Nippon Kagaku Zasshi, 1956, vol. 77, p. 682,685[5] Chem.Abstr., 1958, p. 9100
  • 25
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  • [ 18511-72-3 ]
  • [ 51595-55-2 ]
Reference: [1] Journal of Chemical Sciences, 2018, vol. 130, # 6,
  • 26
  • [ 366-18-7 ]
  • [ 79-22-1 ]
  • [ 71071-46-0 ]
YieldReaction ConditionsOperation in experiment
98.2% With phosphotungstic acid; sodium tungstate; titanium(IV) oxide; zirconium(IV) oxide; triethylamine In methanol at 90℃; for 5 h; Inert atmosphere The 2,2 '-bipyridine, methyl chloroformate, diethylamine, methanol and catalyst were mixed , then passes nitrogen gas and the reaction was carried out at 90 ° C at 3 MPa for 5 hours. In step 1), the molar ratio of 2,2 '-bipyridine, methyl chloroformate, triethylamine is 1: 2: 5; dose ratio  of 2,2 '-bipyridine, methanol and catalyst is 1mol: 500ml: 0.3g;the mentioned catalyst was prepared by the following method: The phosphotungstic acid and sodium tungstate were dissolved in water and added a mixture of nanometer titanium dioxide and nano zirconia which is 6 times the weight of phosphotungstic acid (this mixture contained 70percent by weight of titanium dioxide), stirred the reaction at 60 ° C for 30 h, then vacuum dried the moisture , an dried at 160 ° C for 2h; The mass ratio of the phosphotungstic acid, sodium tungstate and water is 1: 0.15: 5;after completion of the reaction, the mixture was filtered to remove insoluble matter, added to water, and extracted with ethyl acetate. After concentration, the product was obtained as a white solid 2,2'-bipyridinyl-4,4'-carboxylic acid methyl ester in a yield of 98.2percent.
Reference: [1] Patent: CN106946772, 2017, A, . Location in patent: Paragraph 0017
  • 27
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  • [ 4926-28-7 ]
  • [ 108-89-4 ]
  • [ 366-18-7 ]
  • [ 1134-35-6 ]
  • [ 56100-19-7 ]
YieldReaction ConditionsOperation in experiment
45 %Chromat. With nickel(II) bromide hydrate; 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.
Reference: [1] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
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  • [ 110-86-1 ]
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  • [ 1134-35-6 ]
  • [ 56100-19-7 ]
YieldReaction ConditionsOperation in experiment
35 %Chromat. With nickel(II) bromide hydrate; 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.
Reference: [1] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
  • 29
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  • [ 13040-77-2 ]
Reference: [1] Journal of the Chinese Chemical Society, 2003, vol. 50, # 2, p. 189 - 192
[2] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 4, p. 1071 - 1077
[3] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 4, p. 1071 - 1077
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  • [ 14162-94-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 4, p. 1071 - 1077
  • 31
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  • [ 14162-95-9 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 18, p. 6653 - 6661
[2] Synthesis, 1998, # 3, p. 321 - 324
[3] Molecules, 2011, vol. 16, # 6, p. 4615 - 4631
[4] Molecules, 2011, vol. 16, # 10, p. 8353 - 8367
[5] Patent: US2012/247546, 2012, A1,
[6] Chemical Papers, 2012, vol. 66, # 8, p. 733 - 740
[7] Tetrahedron Letters, 2013, vol. 54, # 40, p. 5514 - 5517
[8] Tetrahedron Letters, 2013, vol. 54, # 40, p. 5514 - 5517
[9] Polyhedron, 2014, vol. 67, p. 381 - 387
[10] Journal of Inorganic Biochemistry, 2014, vol. 134, p. 83 - 91
[11] Inorganic Chemistry, 2015, vol. 54, # 6, p. 2742 - 2751
[12] Monatshefte fur Chemie, 2017, vol. 148, # 6, p. 991 - 998
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  • [ 99970-84-0 ]
Reference: [1] Journal of Chemical Sciences, 2018, vol. 130, # 6,
  • 33
  • [ 366-18-7 ]
  • [ 917-54-4 ]
  • [ 56100-22-2 ]
YieldReaction ConditionsOperation in experiment
63.8% at 0℃; for 5 h; Inert atmosphere; Reflux Methyllithium (1.3 M, 33.80 mmol) in THF (26 mL) was added dropwise to a solution of 2,2'-bipyridine (5.30 g, 34.00 mmol) in diethyl ether (100 mL) at 0 °C under N2 atmosphere. The reaction mixture was stirred for 2 h, and then refluxed for 3 h. Water (10 mL) was added when the mixture cooled to room temperature. The organic layer was separated and the aqueous layer was extracted three times with ether. The combined organic layer was dried by anhydrous Na2SO4. The solvent was removed by evaporation. The resulting orange oil was oxidized with saturated KMnO4/acetone (300 mL) and stirred for 1 h. The filtrate was placed in a flask and acetone was removed by evaporation. The resulting dark oil was distilled under vacuum and finally gave pure 6-methyl-2,2'-bipyridine as colourless oil (3.73 g, 63.8percent). 1H NMR (400 MHz, CDCl3) δ ppm: 8.65 (s, 1H), 8.38 (d, J = 8.0 Hz, 1H), 8.15 (d, J = 7.9 Hz, 1H), 7.72-7.82 (m, 1H), 7.66 (d, J = 7.7 Hz, 1H), 7.21-7.30 (m, 1H), 7.13 (d, J = 7.7 Hz, 1H), 2.61 (s, 3H). 13C NMR (100 MHz, CDCl3) δ ppm: 157.7, 156.3, 155.4, 149.0, 136.9, 136.7, 123.6, 123.2, 121.02, 117.9, 24.5. ESI-MS (m/z): calcd for C11H10N2 [M + H]+ 171.22, found 171.61.
63.8% at 0℃; for 5 h; Inert atmosphere; Reflux 5.30 g of 2,2'-bipyridine was placed in a three-necked flask,Nitrogen and reduced to below 0 & lt; 0 & gt; C with an ice bath,Then take 100 ml of dry ether to the flask to 2,2 '- bipyridine all dissolved;Another 26 ml of methyl lithium (1.3 moles per liter) was added dropwise to the flask,The reaction was carried out under ice-cooling for 2 hours and then refluxed for 3 hours.After cooling to room temperature,The reaction was quenched by the addition of 10 ml of water,After separation,The aqueous phase was extracted with ether,The solvent was evaporated,300 ml of a saturated potassium permanganate solution in acetone was added,Stirring for one hour,The produced manganese dioxide was removed by filtration,The solvent was distilled off,The pure product II, 3.278 g, was isolated by distillation under reduced pressure at a yield of 63.8percent.
36% at 0℃; for 0.5 h; Inert atmosphere; Schlenk technique 2,2’-Bipyridyl(180 mg, 1.0 mmol) was added into a 100-mL 2-neck round-bottom flask with amagnetic stirring bar. The flask was evacuated and refilled with N2 gas following theusual Schlenk technique. Dry toluene (30 mL, 0.30 M) was added while stirring andthe reaction mixture was cooled to 0 °C. Methyl lithium in ether solution (3.1 M, 0.32mL, 1.0 mmol, 1.0 equiv) was added dropwise in the course of 30 min, and stirred foran additional 30 min at 0 C. The reaction mixture was quenched with dropwiseaddition of H2O (10 mL). The resulting mixture was extracted with CH2Cl2 (3 10mL) and the combined organic layer was treated with excess MnO2, followed bystirring for 30 min. The crude product was filtered through a pad of Celite® andconcentrated in vacuo. Purification through silica gel column chromatography(hexane/EtOAc = 3:2) and removal of solvent in vacuo gave 6-Mebpy in 36percent (61 mg,0.31 mmol) yield as an oil.
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 23, p. 5872 - 5876
[2] Dyes and Pigments, 2016, vol. 128, p. 33 - 40
[3] Patent: CN105669689, 2016, A, . Location in patent: Paragraph 0032
[4] Angewandte Chemie - International Edition, 2016, vol. 55, # 37, p. 11207 - 11211[5] Angew. Chem., 2016, vol. 128, # 37, p. 11373 - 11377,5
[6] Organic Letters, 2012, vol. 14, # 1, p. 86 - 89
[7] Chemistry Letters, 2018, vol. 47, # 3, p. 329 - 331
[8] Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 8968 - 8979,12
[9] Synthesis, 1992, # 6, p. 519 - 521
[10] Russian Chemical Bulletin, 1997, vol. 46, # 1, p. 202 - 203
[11] Inorganic Chemistry, 2010, vol. 49, # 3, p. 823 - 832
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  • [ 5315-25-3 ]
  • [ 2402-78-0 ]
  • [ 366-18-7 ]
  • [ 4411-80-7 ]
  • [ 57154-73-1 ]
  • [ 33777-92-3 ]
  • [ 56100-22-2 ]
YieldReaction ConditionsOperation in experiment
47% With [Ni(2,2'-bipyridine)2Br2]; sodium iodide In N,N-dimethyl-formamide at 20℃; for 8 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 20 min. Then the current was stopped, and [Ni(bpy)]Br2 complex21 (2.6 mmol, 562 mg), 2,6-dichloropyridine (5 mmol, 0.74 g), and 2-bromo-6-methylpyridine (10 mmol, 1.72 g) were sequentially added. The solution was electrolyzed at 0.1 A and room temperature until the starting material was totally consumed (8 h).
Reference: [1] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
  • 35
  • [ 109-04-6 ]
  • [ 5315-25-3 ]
  • [ 366-18-7 ]
  • [ 4411-80-7 ]
  • [ 56100-22-2 ]
YieldReaction ConditionsOperation in experiment
56 %Chromat. With nickel(II) bromide hydrate; 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.
Reference: [1] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
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  • [ 5315-25-3 ]
  • [ 2402-78-0 ]
  • [ 366-18-7 ]
  • [ 4411-80-7 ]
  • [ 1170693-78-3 ]
  • [ 57154-73-1 ]
  • [ 33777-92-3 ]
  • [ 56100-22-2 ]
YieldReaction ConditionsOperation in experiment
16% With [Ni(2,2'-bipyridine)2Br2]; sodium iodide In N,N-dimethyl-formamide at 20℃; for 8 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 20 min. Then the current was stopped, and [Ni(bpy)]Br2 complex21 (2.6 mmol, 562 mg), 2,6-dichloropyridine (5 mmol, 0.74 g), and 2-bromo-6-methylpyridine (10 mmol, 1.72 g) were sequentially added. The solution was electrolyzed at 0.1 A and room temperature until the starting material was totally consumed (8 h).
Reference: [1] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
  • 37
  • [ 366-18-7 ]
  • [ 56100-22-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 1984, vol. 19, # 5, p. 399 - 404
  • 38
  • [ 2402-78-0 ]
  • [ 110-86-1 ]
  • [ 366-18-7 ]
  • [ 53344-72-2 ]
YieldReaction ConditionsOperation in experiment
25 %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.
40 %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.
Reference: [1] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
[2] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
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  • [ 366-18-7 ]
  • [ 53344-72-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 1980, p. 2527 - 2530
[2] Dalton Transactions, 2017, vol. 46, # 7, p. 2238 - 2248
[3] Research on Chemical Intermediates, 2017, vol. 43, # 6, p. 3539 - 3552
  • 40
  • [ 366-18-7 ]
  • [ 79-37-8 ]
  • [ 1201-31-6 ]
  • [ 94695-48-4 ]
  • [ 94695-50-8 ]
Reference: [1] Patent: US4617308, 1986, A,
  • 41
  • [ 366-18-7 ]
  • [ 103505-54-0 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 10, p. 3379 - 3385
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  • [ 46389-47-3 ]
Reference: [1] Journal of Organometallic Chemistry, 1990, vol. 393, # 1, p. 137 - 142
[2] Russian Journal of General Chemistry, 2002, vol. 72, # 2, p. 168 - 172
[3] New Journal of Chemistry, 2002, vol. 26, # 2, p. 207 - 212
[4] Russian Chemical Bulletin, 2002, vol. 51, # 5, p. 796 - 804[5] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 2002, vol. 51, # 5, p. 734 - 741
[6] Russian Chemical Bulletin, 2003, vol. 52, # 3, p. 567 - 569
[7] Organometallics, 2010, vol. 29, # 22, p. 6002 - 6011
[8] Russian Chemical Bulletin, 2005, vol. 54, # 4, p. 942 - 947
[9] Patent: KR101581821, 2015, B1, . Location in patent: Paragraph 0041; 0043
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  • [ 1295-35-8 ]
  • [ 12145-47-0 ]
  • [ 5259-72-3 ]
  • [ 46389-47-3 ]
  • [ 917346-05-5 ]
Reference: [1] Journal of Organometallic Chemistry, 2006, vol. 691, # 23, p. 4868 - 4873
  • 44
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  • [ 46389-47-3 ]
Reference: [1] Russian Journal of General Chemistry, 2001, vol. 71, # 1, p. 128 - 131
[2] New Journal of Chemistry, [3] New Journal of Chemistry, 1989, vol. 13, p. 53 - 60
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