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[ CAS No. 53344-72-2 ] {[proInfo.proName]}

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Chemical Structure| 53344-72-2
Chemical Structure| 53344-72-2
Structure of 53344-72-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 53344-72-2 ]

CAS No. :53344-72-2 MDL No. :MFCD11042483
Formula : C10H6Cl2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :WYCIUIOCIYSVOZ-UHFFFAOYSA-N
M.W : 225.07 Pubchem ID :10987918
Synonyms :

Calculated chemistry of [ 53344-72-2 ]

Physicochemical Properties

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 : 57.49
TPSA : 25.78 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.59
Log Po/w (XLOGP3) : 3.4
Log Po/w (WLOGP) : 3.45
Log Po/w (MLOGP) : 2.02
Log Po/w (SILICOS-IT) : 3.73
Consensus Log Po/w : 3.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.95
Solubility : 0.0255 mg/ml ; 0.000113 mol/l
Class : Soluble
Log S (Ali) : -3.62
Solubility : 0.0539 mg/ml ; 0.000239 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.41
Solubility : 0.000878 mg/ml ; 0.0000039 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.03

Safety of [ 53344-72-2 ]

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

Application In Synthesis of [ 53344-72-2 ]

* 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 [ 53344-72-2 ]
  • Downstream synthetic route of [ 53344-72-2 ]

[ 53344-72-2 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 109-09-1 ]
  • [ 53344-72-2 ]
YieldReaction ConditionsOperation in experiment
47%
Stage #1: With n-butyllithium; lithium 2-(dimethylamino)ethanolate In hexane at -20 - 0℃; for 1 h;
Stage #2: at -20 - 0℃;
The 6,6'-dichloro-2,2'-bipyridine 52a was synthesized by reacting 2-chloropyridine with a mixture of BuLi/Me2N(CH2)2OLi as base for the regioselective lithiation at C-6 (Scheme 23). The 6-lithio-2-chloro-pyridine obtained appears to react with the starting chloropyridine so as to give the corresponding coupling product 52a with a yield of 47percent.
Reference: [1] Organic Letters, 2000, vol. 2, # 6, p. 803 - 805
[2] Patent: US2010/298562, 2010, A1, . Location in patent: Page/Page column 34
[3] Organic Letters, 2000, vol. 2, # 6, p. 803 - 805
[4] Phosphorus and Sulfur and the Related Elements, 1987, vol. 34, p. 123 - 132
[5] Patent: CN107935919, 2018, A, . Location in patent: Paragraph 0049; 0051
  • 2
  • [ 5140-72-7 ]
  • [ 53344-72-2 ]
YieldReaction ConditionsOperation in experiment
35% at 100℃; The 6,6'-dichloro-2,2'-bipyridine 52a can also be prepared via Stille heterocoupling between the 2-bromo-6-chloropyridine 55 and the 2-chloro-6-tributylstannylpyridine 56, with a yield of 35percent (Scheme 25).
Reference: [1] Organic Letters, 2000, vol. 2, # 6, p. 803 - 805
[2] Patent: US2010/298562, 2010, A1, . Location in patent: Page/Page column 34
  • 3
  • [ 103505-54-0 ]
  • [ 53344-72-2 ]
YieldReaction ConditionsOperation in experiment
93% 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.
Reference: [1] Patent: US2010/298562, 2010, A1, . Location in patent: Page/Page column 34
  • 4
  • [ 2402-78-0 ]
  • [ 1361327-25-4 ]
  • [ 53344-72-2 ]
YieldReaction ConditionsOperation in experiment
46% 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).
Reference: [1] Tetrahedron, 2012, vol. 68, # 10, p. 2383 - 2390
  • 5
  • [ 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
  • 6
  • [ 18412-57-2 ]
  • [ 258506-66-0 ]
  • [ 864913-65-5 ]
  • [ 53344-72-2 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 20, p. 5378 - 5381
  • 7
  • [ 2402-78-0 ]
  • [ 201230-82-2 ]
  • [ 98-80-6 ]
  • [ 13382-54-2 ]
  • [ 80099-99-6 ]
  • [ 53344-72-2 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 16, p. 2793 - 2799
  • 8
  • [ 130896-97-8 ]
  • [ 53344-72-2 ]
Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 32, p. 4625 - 4628
  • 9
  • [ 87512-28-5 ]
  • [ 53344-72-2 ]
Reference: [1] Phosphorus and Sulfur and the Related Elements, 1987, vol. 34, p. 123 - 132
  • 10
  • [ 7275-43-6 ]
  • [ 53344-72-2 ]
Reference: [1] Dalton Transactions, 2017, vol. 46, # 7, p. 2238 - 2248
[2] Journal of the Chinese Chemical Society, 2012, vol. 59, # 8, p. 934 - 939
[3] Research on Chemical Intermediates, 2017, vol. 43, # 6, p. 3539 - 3552
  • 11
  • [ 13267-48-6 ]
  • [ 53344-72-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 1980, p. 2527 - 2530
  • 12
  • [ 39588-57-3 ]
  • [ 53344-72-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 9, p. 2710 - 2712
  • 13
  • [ 87512-28-5 ]
  • [ 7654-51-5 ]
  • [ 53344-72-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 12, p. 3848 - 3850
  • 14
  • [ 17228-64-7 ]
  • [ 53344-72-2 ]
Reference: [1] Patent: US2010/298562, 2010, A1,
  • 15
  • [ 21948-80-1 ]
  • [ 87512-28-5 ]
  • [ 119-91-5 ]
  • [ 53344-72-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 12, p. 3848 - 3850
  • 16
  • [ 2895-98-9 ]
  • [ 53344-72-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 9, p. 2710 - 2712
  • 17
  • [ 77145-64-3 ]
  • [ 53344-72-2 ]
Reference: [1] Phosphorus and Sulfur and the Related Elements, 1987, vol. 34, p. 123 - 132
  • 18
  • [ 39858-88-3 ]
  • [ 53344-72-2 ]
Reference: [1] Patent: US2010/298562, 2010, A1,
  • 19
  • [ 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
  • 20
  • [ 7275-43-6 ]
  • [ 1762-41-0 ]
  • [ 85591-65-7 ]
  • [ 53344-72-2 ]
Reference: [1] Tetrahedron, 1983, vol. 39, # 2, p. 291 - 296
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