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[ CAS No. 99163-12-9 ] {[proInfo.proName]}

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Chemical Structure| 99163-12-9
Chemical Structure| 99163-12-9
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Product Details of [ 99163-12-9 ]

CAS No. :99163-12-9 MDL No. :MFCD02684110
Formula : C12H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :MBJXDIYHLGBQOT-UHFFFAOYSA-N
M.W : 183.21 Pubchem ID :639673
Synonyms :

Calculated chemistry of [ 99163-12-9 ]

Physicochemical Properties

Num. heavy atoms : 14
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 : 55.06
TPSA : 29.96 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) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : 2.05
Log Po/w (WLOGP) : 2.56
Log Po/w (MLOGP) : 1.41
Log Po/w (SILICOS-IT) : 3.17
Consensus Log Po/w : 2.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.77
Solubility : 0.311 mg/ml ; 0.0017 mol/l
Class : Soluble
Log S (Ali) : -2.31
Solubility : 0.902 mg/ml ; 0.00492 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.49
Solubility : 0.00593 mg/ml ; 0.0000324 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.25

Safety of [ 99163-12-9 ]

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 [ 99163-12-9 ]

* 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 [ 99163-12-9 ]
  • Downstream synthetic route of [ 99163-12-9 ]

[ 99163-12-9 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 99163-12-9 ]
  • [ 4385-76-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 3, p. 631 - 634
  • 2
  • [ 1692-15-5 ]
  • [ 1122-91-4 ]
  • [ 99163-12-9 ]
YieldReaction ConditionsOperation in experiment
68.4% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran; toluene at 90℃; Inert atmosphere Compound P-formaldehyde (500 mg, 2 . 70mmol), 4-boronic acid pyridine (498.3 mg, 4 . 05mmol), double (triphenylporphyrin phosphorus) palladium dichloride Pd (PPh3)2Cl2(94.65 mg, 0 . 14mmol), dissolved in 20 ml tetrahydrofuran mixed solvent of toluene and (Vtoluene: VTHF= 1:1) in, under the protection of nitrogen 90 °C reflux reaction, thin-layer chromatography tracking to the reaction is complete. The solution obtained after the organic solvent, a revolving off, the extraction with ethyl acetate, the organic layer three times washing with water, saturated NaCl solution to a washing, drying by anhydrous sodium sulfate, reducing pressure and evaporating the solvent. The crude product using petroleum ether and ethyl acetate mixed solvent (20:1) column, to obtain 4 - (pyridin-4-yl) benzaldehyde (white solid, 288.7 mg, yield 68.4percent).
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 21, p. 6622 - 6630
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 18, p. 8402 - 8416
[3] Crystal Growth and Design, 2018, vol. 18, # 11, p. 6936 - 6945
[4] Patent: CN105418515, 2016, A, . Location in patent: Paragraph 0087; 0088; 0089
[5] Angewandte Chemie - International Edition, 2006, vol. 45, # 17, p. 2761 - 2766
[6] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 453 - 462
  • 3
  • [ 1120-87-2 ]
  • [ 87199-17-5 ]
  • [ 99163-12-9 ]
Reference: [1] Organic Letters, 2004, vol. 6, # 19, p. 3337 - 3340
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 8049 - 8065
  • 4
  • [ 1120-87-2 ]
  • [ 24856-58-4 ]
  • [ 99163-12-9 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 2 h;
Stage #2: at 50℃; for 2.5 h;
Anhydrous zinc chloride (6.8 g, 0.050 moles) and then 4-bromopyridine (26.4 g, 0.16 mol) are added, with agitation under an inert atmosphere, to a solution constituted by toluene (78 g) and tetrahydrofuran (66 g). [00127] Palladium tetrakistriphenylphosphine (0.102 g, 0.089 mmol) and then, over a period of 2 hours, a solution of the Grignard reagent of 4-bromobenzaldehyde dimethyl acetal (169.3 g of solution, equal to 0.197 mol) prepared analogously to Example 1, are added to the suspension maintained at 50° C. with agitation and under an inert atmosphere. [00128] The reaction mixture is maintained at 50° C. for 30 minutes and then cooled to 25° C. [00129] 4-(4'-pyridyl)benzaldehyde (27.5 g, 0.15 mol) is obtained with a yield of 90percent in moles relative to the 4-bromopyridine added, turnover of the catalyst (Pd): 1685.
Reference: [1] Patent: US6765097, 2004, B1, . Location in patent: Page column 14
  • 5
  • [ 25108-37-6 ]
  • [ 1122-91-4 ]
  • [ 99163-12-9 ]
YieldReaction ConditionsOperation in experiment
38% With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); 1,10-Phenanthroline In N,N-dimethyl acetamide at 60 - 180℃; for 4 h; Inert atmosphere; Glovebox; Microwave irradiation General procedure: In an argon-filled glovebox, a 10 mL microwave vial was charged with Pd(PPh3)4 (14.35 mg,0.0125 mmol), Cu2O (21.3 mg, 0.15 mmol), 1,10-phenanthroline (8.95 mg,0.05 mmol), the potassium pyridylcarboxylate (0.50 mmol), aryl bromide(0.75 mmol) and anhydrous DMA (3.0 mL). The resulting solution wasirradiated in a microwave reactor (Biotage Initiator Eight EXP) with a 2 minprestirring period, followed by 10 min at 60 C. The reaction was then heatedat 180 C for 3 h 50 min. The maximum pressure noted was 3 bar. Aftercompletion of the reaction, H2O was added to the mixture which was thenextracted with EtOAc (3 10 mL). The combined organic layers were washedwith brine (5 mL), dried over Na2SO4, filtered, and the volatiles removed invacuo. The residue was purified by column chromatography on silica gel,yielding the corresponding biaryl product.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 11, p. 1293 - 1296
  • 6
  • [ 4423-10-3 ]
  • [ 99163-12-9 ]
Reference: [1] Journal of the American Chemical Society, 2002, vol. 124, # 10, p. 2245 - 2258
[2] Journal of the American Chemical Society, 2001, vol. 123, # 13, p. 3183 - 3185
  • 7
  • [ 87199-17-5 ]
  • [ 19524-06-2 ]
  • [ 99163-12-9 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 23, p. 4985 - 4992
[2] Chemistry - A European Journal, 2017, vol. 23, # 42, p. 10017 - 10022
[3] Angewandte Chemie - International Edition, 2010, vol. 49, # 22, p. 3757 - 3761
[4] Green Chemistry, 2018, vol. 20, # 9, p. 1975 - 1980
[5] Molecules, 2003, vol. 8, # 7, p. 556 - 564
[6] Patent: US6548494, 2003, B1,
[7] Chemical Communications, 2008, # 24, p. 2794 - 2796
  • 8
  • [ 15854-87-2 ]
  • [ 87199-17-5 ]
  • [ 99163-12-9 ]
Reference: [1] Chemistry - An Asian Journal, 2018, vol. 13, # 9, p. 1108 - 1113
  • 9
  • [ 61568-51-2 ]
  • [ 99163-12-9 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 9, p. 1975 - 1980
  • 10
  • [ 1122-91-4 ]
  • [ 99163-12-9 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 9, p. 1975 - 1980
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