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[ CAS No. 4783-68-0 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 4783-68-0
Chemical Structure| 4783-68-0
Chemical Structure| 4783-68-0
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Product Details of [ 4783-68-0 ]

CAS No. :4783-68-0 MDL No. :MFCD00047432
Formula : C11H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :MEAAWTRWNWSLPF-UHFFFAOYSA-N
M.W : 171.20 Pubchem ID :78510
Synonyms :

Calculated chemistry of [ 4783-68-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.75
TPSA : 22.12 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) : -5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 2.39
Log Po/w (WLOGP) : 2.87
Log Po/w (MLOGP) : 2.15
Log Po/w (SILICOS-IT) : 2.56
Consensus Log Po/w : 2.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.96
Solubility : 0.188 mg/ml ; 0.0011 mol/l
Class : Soluble
Log S (Ali) : -2.5
Solubility : 0.547 mg/ml ; 0.00319 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.28
Solubility : 0.00905 mg/ml ; 0.0000528 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.01

Safety of [ 4783-68-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4783-68-0 ]

* 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 [ 4783-68-0 ]

[ 4783-68-0 ] Synthesis Path-Downstream   1~85

  • 2
  • [ 109-04-6 ]
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YieldReaction ConditionsOperation in experiment
95% With 2-Picolinic acid; potassium phosphate; copper(l) iodide; In dimethyl sulfoxide; at 90℃; for 24h;Inert atmosphere; (2) The phenol 1.2mmol, tripotassium phosphate 2mmol,2-pyridyl acid 0.1mmol,Bromopyridine 1mmol, cuprous iodide 0.05mmol, 2ml DMSO, 25ml of three bottle. The mixture under argon protection, at the end of 90 reflux for 24 hours the reaction by TLC, the resulting mixed solution was extracted with ethyl acetate, dried over anhydrous sodium sulfate and the solvent removed under reduced pressure to give a pale yellow solid2- (phenoxy) pyridine (95% yield).
95% With 2-Picolinic acid; potassium phosphate; copper(l) iodide; In dimethyl sulfoxide; at 90℃; for 24h;Inert atmosphere; 1.2 mmol of phenol,Tripotassium phosphate 2mmol,2-picolinic acid 0.1 mmol, 2-bromopyridine 1 mmol,Cuprous iodide 0.05 mmol,2 ml DMSO,Add 25ml three bottles.The mixture was protected under argon,The reaction was terminated after TLC was refluxed at 90 C for 24 hours,The resulting mixed solution was extracted with ethyl acetate, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure.To give 2- (phenoxy) pyridine as a pale yellow solid (95% yield).
84% With copper(II) oxide; potassium hydroxide; In N,N-dimethyl acetamide; at 27℃;Inert atmosphere; Sealed tube; General procedure: A magnetic stirring bar, nanocrystalline CuO (10 mg, 3 mol %), KOH (112 mg, 2 mmol) and phenol/substituted phenol/ thiophenol (1.2 mmol) were added into an oven-dried flask (25 mL). The flask was sealed with a septum, followed by three cycles of evacuation and filling with dry nitrogen. Then aryl halide (1 mmol) and N,N-dimethyl acetamide (DMAc) (4 mL) were injected through a syringe. The flask was sealed and stirred under nitrogen until the completion of the reaction (as monitored by TLC or GC). The catalyst was recovered from the reaction mixture and washed several times with ethyl acetate. The catalyst-free reaction mixture was quenched with brine solution and the product was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (hexane/ethyl acetate, 80/20) to afford the product with high purity.
81% With tetrabutylammomium bromide; caesium carbonate; In N,N-dimethyl-formamide; at 145℃; for 24h;Inert atmosphere; General procedure: To a stirred solution of phenol (2.2mmol) in DMF (15.0mL) under an argon atmosphere were added CuO-Fe3O4 (0.2mmol), TBAB (0.2mmol), Cs2CO3 (326mg, 1.0mmol) and aryl halide (2.0mmol). The reaction mixture was stirred at the required temperature (145C) for 24 h. At the end of reaction, the catalyst was removed by a magnet and the resulting mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to remove the solvent. The residue was purified by column chromatography on silica gel to afford the desired product.
81% With sodium dodecyl-sulfate; potassium carbonate; In water; at 80℃; under 760.051 Torr; for 10h;Green chemistry; General procedure: To a stirred suspension of appropriate aryl halide(2.0 mmol) and phenol (2.0 mmol) in 6 ml water, Ni-alumina (0.125g, 6 mol % ofnickel metal) was added followed by K2CO3 (0.28 g, 2mmol) and SDS (0.04 g, 8 mol%). The reaction mixture was stirred for therequired period of time at 80C till the reaction was complete (monitored withTLC). Then the reaction mixture was cooled to room temperature, ethyl acetate(20 mL) was added to dissolve the product and the catalyst was separated simplyby filtration. The residue (recovered catalyst) was thoroughly washed withEtOAc (4×5 mL) followed by water (2×10 mL). The aqueous reaction mixture was repeatedly extracted with ethyl acetate (3×5 mL). The combined organic extractswere washed with water (3× 10 mL) and dried over anhydrous Na2SO4.The crude product was obtained by removal of the solvent under reduced pressure which was furtherpurified by filtration chromatography on a short column of silica gel using1-4% ethyl acetate-hexane as eluent.
80% With 2-Picolinic acid; potassium phosphate; copper(l) iodide; In dimethyl sulfoxide; at 80℃; for 24h;Inert atmosphere; 1.57 g (10.0 mmol) of 2-bromopyridine,Cuprous iodide 0.10 g (0.5 mmol)Pyridine-2-carboxylic acid 0.124 g (0.1 mmol), tripotassium phosphate4.240g(20.0 mmol),Phenol (1.128 g, 12.0 mmol), and 20 ml of DMSO were added to a 100 ml flask.The mixture was heated to 80 C under nitrogen for 24 hours. After 24 hours of reaction, the TLC reaction was terminated,Diluted with 50 ml of ethyl acetate,Water extraction,After the organic phase was dried, the solvent was removed under reduced pressure,The residue was purified by column chromatography [GF254 silica gel;100-200 heads;The developing solvent was purified by purification of V (petroleum ether) / V (ethyl acetate) = 10/1]Collecting the eluate containing the product,The solvent was distilled off to give 1.368 g (80% yield) of 2-phenoxypyridine.

  • 3
  • [ 4783-68-0 ]
  • [ 75-03-6 ]
  • 1-ethyl-2-phenoxy-pyridinium; iodide [ No CAS ]
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  • [ 74-88-4 ]
  • [ 58801-92-6 ]
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  • [ 142-08-5 ]
  • [ 462-80-6 ]
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  • [ 142-08-5 ]
  • [ 462-80-6 ]
  • [ 13131-02-7 ]
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  • [ 37520-79-9 ]
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  • [ 109-09-1 ]
  • [ 108-95-2 ]
  • [ 4783-68-0 ]
YieldReaction ConditionsOperation in experiment
77% With sodium dodecyl-sulfate; potassium carbonate; In water; at 80℃; under 760.051 Torr; for 10h;Green chemistry; General procedure: To a stirred suspension of appropriate aryl halide(2.0 mmol) and phenol (2.0 mmol) in 6 ml water, Ni-alumina (0.125g, 6 mol % ofnickel metal) was added followed by K2CO3 (0.28 g, 2mmol) and SDS (0.04 g, 8 mol%). The reaction mixture was stirred for therequired period of time at 80C till the reaction was complete (monitored withTLC). Then the reaction mixture was cooled to room temperature, ethyl acetate(20 mL) was added to dissolve the product and the catalyst was separated simplyby filtration. The residue (recovered catalyst) was thoroughly washed withEtOAc (4×5 mL) followed by water (2×10 mL). The aqueous reaction mixture was repeatedly extracted with ethyl acetate (3×5 mL). The combined organic extractswere washed with water (3× 10 mL) and dried over anhydrous Na2SO4.The crude product was obtained by removal of the solvent under reduced pressure which was furtherpurified by filtration chromatography on a short column of silica gel using1-4% ethyl acetate-hexane as eluent.
With 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(l) chloride; In 1-methyl-pyrrolidin-2-one; at 120℃; for 24h;Inert atmosphere; General procedure: A mixture of cesium carbonate (3.2 g, 10 mmol), 2-chloropyridine (567 mg, 10 mmol), CuCl (25 mg, 2.5 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (92 mg, 0.5 mmol), and phenols (10 mmol) in NMP (8 mL) was degassed and filled with nitrogen three times. After the slurry was heated at 120 C under nitrogen for 24 h, it was cooled to room temperature and diluted with EtOAc. The organic layer was washed subsequently with 2 M NaOH (30 mL) and saturated brine (3×30 mL). The resulting organic layer was dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2: n-hexanes/EtOAc) to give the corresponding phenoxy-2-pyridines.
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  • [ 83247-00-1 ]
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  • [ 372-48-5 ]
  • [ 108-95-2 ]
  • [ 4783-68-0 ]
YieldReaction ConditionsOperation in experiment
18% Phenol (3.37 g, 35.88 mmol) in dioxane (15 mL) was added dropwise to sodium hydride (60% dispersion in mineral oil) (1.67 g, 41.75 mmol) under a nitrogen atmosphere. After stirring at room temperature for lhour, 2-fluoro-pyridine (2.9 g, 29.9 mmol) in dioxane (15 mL) was added and the resulting mixture stirred at 80 C for 48 hours. The mixture was concentrated in vacuo, and then partitioned between DCM and saturated potassium carbonate solution. The organic layer was washed twice with saturated potassium carbonate solution, dried over sodium sulfate and concentrated invacuo to give an oil. This oil was partitioned between acetonitrile (20 mL) and hexane (20 mL). The acetonitrile layer was collected, dried and concentrated in vacuo to give 2-plienoxy-pyridine (950 mg, 18%). 8H (400 MHz, CDCI3) 8.20 (1H, dd J 4.7, 1.7 Hz, Ar), 7.71-7. 65 (1H, m, Ar), 7.40 (2H, t J 7.9 Hz, Ar), 7.20 (1H, t J 7.4 Hz, Ar), 7.14 (2H, dd J 8.5, 1.0 Hz, Ar), 6. 99 (1H, dd J 7.1, 5.0 Hz, Ar), 6.90 (1H, d J 8. 3 Hz, Ar); Tr = 1.20 min (97%), mlz (ES+) (M+H)+ 172. 02
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  • [ 2127-03-9 ]
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  • [ 107263-95-6 ]
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  • [ 107264-09-5 ]
  • [ 108-95-2 ]
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  • [ 108-95-2 ]
  • sodium pyridine isodiazotate-(2) [ No CAS ]
  • [ 4783-68-0 ]
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  • [ 142-08-5 ]
  • [ 118-92-3 ]
  • isopentenzlnitrit [ No CAS ]
  • [ 13131-02-7 ]
  • [ 4783-68-0 ]
  • 5,6-benzo-2-azabarrelen-3(2H)-one [ No CAS ]
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  • [ 7647-01-0 ]
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  • [ 109-09-1 ]
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  • [ 5029-67-4 ]
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  • [ 372-48-5 ]
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  • [ 617-86-7 ]
  • [ 4783-68-0 ]
  • 2-(2-triethylsilanyl-phenoxy)-pyridine [ No CAS ]
  • 2-(2,6-bis-triethylsilanyl-phenoxy)-pyridine [ No CAS ]
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  • [ 109-09-1 ]
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  • [ 142-08-5 ]
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  • [ 4783-68-0 ]
  • 4-(pyridin-2-yloxy)-benzenesulfonyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With chlorosulfonic acid; In chloroform; at 0 - 20℃; Chlorosulfonic acid (0.77 mL, 11.69 mmol) was added dropwise to a stirred solution of 2-phenoxy-pyridine (500 mg, 2.92 mmol) in chloroform (10 mL) at 0C. The mixture was left at 0C for 30 minutes, and then left overnight stirring at room temperature. Three other treatments with chlorosulfonic acid (3 x 0.38 mL, 3 x 5. 84 mmol) were required to give complete conversion to the sulfonyl chloride. The resulting mixture was then poured slowly onto a mixture of ice and water (250 mL). The aqueous layer was extracted with dichloromethane (250 mL). The resulting organic layer was washed with water (20 mL), dried over sodium sulfate, filtered and concentrated in vacuo to give 4- (pyridin-2-yloxy)-benzenesulfonyl chloride (440 mg, 56%).
(h) 4-(Pyrid-2-yl)oxybenzenesulfonyl chloride Prepared from <strong>[4783-68-0]2-phenoxypyridine</strong> (ICN): 1H NMR (CDCl3) d 8.25 (m, 1H), 8.05 (d, 2H, J=9 Hz), 7.81 (t, 1H, J=8 Hz), 7.34 (d, 2H, J=9 Hz), 7.15 (dd, 1H, J=7 & 5 Hz), 7.06 (d, 1H, J=8 Hz).
Example 1(h) 4-(Pyrid-2-yl)oxybenzenesulfonyl chloride STR19 From <strong>[4783-68-0]2-phenoxypyridine</strong> (supplier: ICN): 1 H NMR (CDCl3) d 8.25 (m, 1H), 8.05 (d, 2H, J=9 Hz), 7.81 (t, 1H, J=8 Hz), 7.34 (d, 2H, J=9 Hz), 7.15 (dd, 1 H, J=7 & 5 Hz), 7.06 (d, 1H, J=8 Hz).
(h) 4-(Pyrid-2-yl)oxybenzenesulfonyl chloride Prepared from <strong>[4783-68-0]2-phenoxypyridine</strong> (ICN): 1H NMR (CDCl3) d 8.25 (m, 1H), 8.05 (d, 2H, J=9 Hz), 7.81 (t, 1H, J=8 Hz), 7.34 (d, 2H, J=9 Hz), 7.15 (dd, 1 H, J=7 & 5 Hz), 7.06 (d, 1H, J=8 Hz).
Example 1 (i) 4-(Pyrid-2-yl)oxybenzenesulfonyl chloride From <strong>[4783-68-0]2-phenoxypyridine</strong> (supplier: ICN): 1H-NMR (CDCl3) delta 8.25 (m, 1H), 8.05 (d, 2H, J=9 Hz), 7.81 (t, 1H, J=8 Hz), 7.34 (d, 2H, J=9 Hz), 7.15 (dd, 1H, J=7 & 5 Hz), 7.06 (d, 1H, J=8 Hz).

  • 39
  • [ 3375-31-3 ]
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  • 2Pd(2+)*2NC5H4OC6H4(1-)*2CH3COO(1-)=[Pd(NC5H4OC6H4)(CH3COO)]2 [ No CAS ]
  • 40
  • hydrogen tetrachloroaurate(III) tetrahydrate [ No CAS ]
  • [ 4783-68-0 ]
  • [ 220693-26-5 ]
  • 41
  • sodium tetrachloroaurate(III) dihyrate [ No CAS ]
  • [ 4783-68-0 ]
  • [ 220693-30-1 ]
  • 42
  • hydrogen tetrachloroaurate(III) tetrahydrate [ No CAS ]
  • [ 4783-68-0 ]
  • [ 220693-28-7 ]
  • 43
  • [ 10203-08-4 ]
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  • [ 1173294-99-9 ]
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  • [ 1122-91-4 ]
  • [ 1173294-98-8 ]
  • 47
  • [bis(μ-2,6-di(p-fluorophenyl)benzoate)bis(2,6-di(p-fluorophenyl)benzoate)bis(tetrahydrofuran)diiron(II)] [ No CAS ]
  • [ 4783-68-0 ]
  • bis(μ-2,6-bis(p-tolyl)benzoate)bis(2,6-bis(p-tolyl)benzoate)bis(2-phenoxyOpyridine)diiron(II) [ No CAS ]
  • 48
  • potassium 4-formylphenyltrifluoroborate [ No CAS ]
  • [ 4783-68-0 ]
  • [ 1246204-69-2 ]
  • 49
  • potassium (4-iodophenyl)trifluoroborate [ No CAS ]
  • [ 4783-68-0 ]
  • [ 1246204-73-8 ]
  • 50
  • potassium trifluoro(2-(methoxycarbonyl)phenyl)borate [ No CAS ]
  • [ 4783-68-0 ]
  • [ 1246204-77-2 ]
  • 51
  • potassium (4-nitrophenyl)trifluoroborate [ No CAS ]
  • [ 4783-68-0 ]
  • [ 1246204-67-0 ]
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  • [ 4783-68-0 ]
  • potassim 4-fluorophenyltrifluoroborate [ No CAS ]
  • [ 1246204-70-5 ]
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  • [ 4783-68-0 ]
  • potassium 4-(methoxy)phenyltrifluoroborate [ No CAS ]
  • [ 1246204-76-1 ]
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  • [ 4783-68-0 ]
  • potassium 3-nitrophenyltrifluoroborate [ No CAS ]
  • [ 1246204-68-1 ]
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  • [ 4783-68-0 ]
  • potassium (4-methylphenyl)trifluoroborate [ No CAS ]
  • [ 1246204-75-0 ]
  • 57
  • [ 4783-68-0 ]
  • [ 374564-35-9 ]
  • [ 1246204-72-7 ]
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  • [ 4783-68-0 ]
  • potassium (4-chlorophenyl)trifluoroborate [ No CAS ]
  • [ 1246204-71-6 ]
  • 59
  • [ 4783-68-0 ]
  • potassium (4-tert-butyl)phenyltrifluoroborate [ No CAS ]
  • [ 1246204-74-9 ]
  • 60
  • [ 3375-31-3 ]
  • [ 4783-68-0 ]
  • [ 239444-41-8 ]
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  • [ 109-09-1 ]
  • [ 108-95-2 ]
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  • [ 104-92-7 ]
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  • [ 1246204-76-1 ]
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  • [ 1357292-93-3 ]
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  • [ 104-92-7 ]
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  • [ 1357292-93-3 ]
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  • [ 4783-68-0 ]
  • C11H8BBr2NO [ No CAS ]
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  • [ 1374790-87-0 ]
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  • [ 501378-40-1 ]
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  • [ 7163-50-0 ]
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  • [ 26767-10-2 ]
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  • [ 7194-78-7 ]
  • [ 4783-68-0 ]
  • (3-bromophenyl)(2-(pyridin-2-yloxy)phenyl)methanone [ No CAS ]
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  • [ 26767-16-8 ]
  • [ 4783-68-0 ]
  • (2-bromophenyl)(2-(pyridin-2-yloxy)phenyl)methanone [ No CAS ]
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