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[ CAS No. 19853-10-2 ] {[proInfo.proName]}

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Chemical Structure| 19853-10-2
Chemical Structure| 19853-10-2
Structure of 19853-10-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 19853-10-2 ]

CAS No. :19853-10-2 MDL No. :MFCD00060294
Formula : C14H11N Boiling Point : -
Linear Structure Formula :- InChI Key :WVYPDPJNPRIPPW-UHFFFAOYSA-N
M.W : 193.24 Pubchem ID :334101
Synonyms :

Calculated chemistry of [ 19853-10-2 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 61.4
TPSA : 23.79 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) : -5.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 3.2
Log Po/w (WLOGP) : 3.42
Log Po/w (MLOGP) : 3.26
Log Po/w (SILICOS-IT) : 3.88
Consensus Log Po/w : 3.19

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.51
Solubility : 0.0592 mg/ml ; 0.000306 mol/l
Class : Soluble
Log S (Ali) : -3.37
Solubility : 0.0822 mg/ml ; 0.000425 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.41
Solubility : 0.000755 mg/ml ; 0.00000391 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 19853-10-2 ]

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:

Application In Synthesis of [ 19853-10-2 ]

* 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 [ 19853-10-2 ]
  • Downstream synthetic route of [ 19853-10-2 ]

[ 19853-10-2 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 2856-63-5 ]
  • [ 98-80-6 ]
  • [ 19853-10-2 ]
Reference: [1] Journal of the American Chemical Society, 1999, vol. 121, # 41, p. 9550 - 9561
[2] Angewandte Chemie - International Edition, 1999, vol. 38, # 16, p. 2413 - 2416
  • 2
  • [ 2856-63-5 ]
  • [ 224311-51-7 ]
  • [ 19853-10-2 ]
YieldReaction ConditionsOperation in experiment
92% With potassium fluoride In tetrahydrofuran EXAMPLE 30
Synthesis of 2-cyanomethylbiphenyl
An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboron dihydroxide (183 mg. 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol).
The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-chlorobenzyl cyanide (152 mg, 1.0 mmol) were added through a rubber septum.
The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis.
The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel.
The mixture was washed with 1.0 M NaOH (20 mL), and the aqueous layer was extracted with ether (20 mL).
The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated.
The crude material was purified by flash chromatography on silica gel to afford 178 mg (92percent) of the title compound.
92% With potassium fluoride In tetrahydrofuran Example 30
Synthesis of 2-cyanomethylbiphenyl
An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboron dihydroxide (183 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol).
The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-chlorobenzyl cyanide (152 mg, 1.0 mmol) were added through a rubber septum.
The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis.
The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel.
The mixture was washed with 1.0 M NaOH (20 mL), and the aqueous layer was extracted with ether (20 mL).
The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated.
The crude material was purified by flash chromatography on silica gel to afford 178 mg (92percent) of the title compound.
Reference: [1] Patent: US6307087, 2001, B1,
[2] Patent: US2004/171833, 2004, A1,
  • 3
  • [ 19853-09-9 ]
  • [ 19853-10-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1929, vol. 468, p. 275
[2] Patent: US2003/212094, 2003, A1,
  • 4
  • [ 1226855-77-1 ]
  • [ 19853-10-2 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 24, p. 12499 - 12505
  • 5
  • [ 17763-65-4 ]
  • [ 1071-36-9 ]
  • [ 19853-10-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 19, p. 4470 - 4474
  • 6
  • [ 75-05-8 ]
  • [ 92-52-4 ]
  • [ 19853-10-2 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 2073 - 2076
  • 7
  • [ 103-81-1 ]
  • [ 19853-10-2 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 24, p. 12499 - 12505
[2] Journal of Organic Chemistry, 2016, vol. 81, # 24, p. 12499 - 12505
  • 8
  • [ 24973-49-7 ]
  • [ 19853-10-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1929, vol. 468, p. 275
  • 9
  • [ 2928-43-0 ]
  • [ 19853-10-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1929, vol. 468, p. 275
  • 10
  • [ 1924-77-2 ]
  • [ 19853-10-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1929, vol. 468, p. 275
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