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[ CAS No. 15889-32-4 ] {[proInfo.proName]}

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Chemical Structure| 15889-32-4
Chemical Structure| 15889-32-4
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Product Details of [ 15889-32-4 ]

CAS No. :15889-32-4 MDL No. :MFCD00956760
Formula : C11H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :YLNMGMIEOWFPRX-UHFFFAOYSA-N
M.W :170.21 Pubchem ID :459517
Synonyms :

Calculated chemistry of [ 15889-32-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.08
TPSA : 38.91 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) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 1.95
Log Po/w (WLOGP) : 2.34
Log Po/w (MLOGP) : 1.47
Log Po/w (SILICOS-IT) : 2.31
Consensus Log Po/w : 1.94

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.74
Solubility : 0.309 mg/ml ; 0.00182 mol/l
Class : Soluble
Log S (Ali) : -2.39
Solubility : 0.69 mg/ml ; 0.00406 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.18
Solubility : 0.0113 mg/ml ; 0.0000665 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 15889-32-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 15889-32-4 ]

* 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 [ 15889-32-4 ]
  • Downstream synthetic route of [ 15889-32-4 ]

[ 15889-32-4 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 109-04-6 ]
  • [ 30418-59-8 ]
  • [ 15889-32-4 ]
YieldReaction ConditionsOperation in experiment
42% With potassium carbonate In 1,2-dimethoxyethane; water at 80℃; REFERENCE EXAMPLE 31; 2-(3-Aminophenyl)pyridine; To a suspension of 2-bromopyridine (0.5 g, 3.2 mmol), 3-aminophenylboronic acid (0.49 g, 3.2 mmol), anhydrous K2CO3 (0.87 g, 6.3 mmol) and Pd(PPh3J4 (0.36 g, 0.32 mmol) in 1 ,2-dimethoxyethane (50 mL) under argon, water (0.66 mL) was added. The mixture was heated under argon at 80 °C overnight. It was allowed to cool and water and EtOAc were added. The phases were separated and the aqueous phase was reextracted with EtOAc. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 0.22 g of the title compound (yield: 42percent). LC-MS (method 1): tR = 1.46 min; m/z = 171.2 [M+H]+.
Reference: [1] Molecular Crystals and Liquid Crystals, 2006, vol. 458, # 1, p. 227 - 235
[2] Journal of Medicinal Chemistry, 2000, vol. 43, # 6, p. 1123 - 1134
[3] Patent: WO2007/339, 2007, A1, . Location in patent: Page/Page column 52
[4] Tetrahedron, 2006, vol. 62, # 49, p. 11483 - 11498
[5] Patent: US2006/94644, 2006, A1, . Location in patent: Page/Page column 23
[6] Patent: WO2007/130743, 2007, A2, . Location in patent: Page/Page column 64
[7] Patent: WO2005/40152, 2005, A1, . Location in patent: Page/Page column 56
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7268 - 7271
  • 2
  • [ 4253-79-6 ]
  • [ 15889-32-4 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8470 - 8475
[2] Patent: US5902813, 1999, A,
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 14, p. 6375 - 6380
[4] Journal of the Chemical Society, 1940, p. 1279,1283
[5] Canadian Journal of Chemistry, 1953, vol. 31, p. 457,466
[6] ChemPlusChem, 2015, vol. 80, # 6, p. 938 - 943
[7] Journal of Medicinal Chemistry, 2017, vol. 60, # 17, p. 7410 - 7424
  • 3
  • [ 109-09-1 ]
  • [ 13331-27-6 ]
  • [ 15889-32-4 ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate; hydrazine hydrate In water; N,N-dimethyl-formamide at 80℃; for 9 h; General procedure: Aryl halide (1.0 mmol), phenylboronic acid (1.1 mmol),K2CO3(2.0 mmol), Ni7–Pd3BIHPS (0.03 g) and H2O/DMF (2:1, 3 mL) were mixed and heated at 80 °C for anappropriate time (monitored by TLC). Then, hydrazinehydrate (80 wtpercent, 6 eq) was added to the reaction vessel.After completion of the reduction process, the mixturewas filtered and washed with water. The organic layer wasextracted with ethyl acetate (3 × 15 mL) and dried overMgSO4.Then the organic solution was concentrated andpurified by column chromatography to obtain the finalproduct.
Reference: [1] Catalysis Letters, 2018, vol. 148, # 8, p. 2446 - 2458
  • 4
  • [ 17997-47-6 ]
  • [ 591-19-5 ]
  • [ 15889-32-4 ]
YieldReaction ConditionsOperation in experiment
64% With tetrakis(triphenylphosphine) palladium(0) In toluene for 12 h; Reflux To a 500 ml round bottom flask was added 20.0 g (116 mmol) of 3-bromoaniline,85.6 g (233 mmol) of 2- (tributylstannyl) pyridine,1.34 g (116 mmol) of tetrakistriphenylphosphine palladium,200 ml of toluene was added and the mixture was refluxed for 12 hours.After completion of the reaction, the temperature was cooled down to room temperature.The organic layer was extracted with ethyl acetate and water and concentrated under reduced pressure.Column purification was carried out using ethyl acetate and n-hexane as eluent. (12.7 g, yield 64percent).
Reference: [1] Patent: KR101897044, 2018, B1, . Location in patent: Paragraph 0154; 0161; 0164-0166
  • 5
  • [ 109-04-6 ]
  • [ 15889-32-4 ]
YieldReaction ConditionsOperation in experiment
37% With sodium carbonate In 1,2-dimethoxyethane; water for 5 h; Reflux (i)
3-(Pyridin-2-yl)aniline
3.72 g (20.0 mmol) of 3-aminophenyl boronic acid* hemisulphate salt, 3.16 g (20.0 mmol) of 2-bromopyridine, 1.16 g (1.0 mmol) of tetrakis(triphenyl phosphine)palladium(0), and 11.2 g (106 mmol) of sodium carbonate were heated under reflux for 5 hours in a mixed solvent of 100 mL of DME and 34 mL of water.
After completion of the reaction, extraction with ethyl acetate, and drying over anhydrous sodium sulfate were carried out.
The solvent was distilled off under reduced pressure.
The resulting crude product was separated and purified using silica gel column chromatography to give 1.27 g of 3-(pyridin-2-yl)aniline (yield: 37percent).
1H-NMR (CDCl3) δ: 3.76 (2H, br), 6.65-6.78 (1H, m), 7.10-7.40 (4H, m), 7.60-7.78 (2H, m), 8.60-8.70 (1H, m).
Reference: [1] Patent: EP2272822, 2011, A1, . Location in patent: Page/Page column 53
  • 6
  • [ 109-04-6 ]
  • [ 626-01-7 ]
  • [ 15889-32-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 2, p. 286 - 297
  • 7
  • [ 626-01-7 ]
  • [ 15889-32-4 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 50, p. 6985 - 6988
[2] Tetrahedron, 2010, vol. 66, # 17, p. 3135 - 3146
  • 8
  • [ 142-08-5 ]
  • [ 30418-59-8 ]
  • [ 15889-32-4 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 48, p. 12840 - 12842
  • 9
  • [ 645-00-1 ]
  • [ 15889-32-4 ]
Reference: [1] ChemPlusChem, 2015, vol. 80, # 6, p. 938 - 943
  • 10
  • [ 1008-89-5 ]
  • [ 15889-32-4 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8470 - 8475
[2] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8470 - 8475
[3] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8470 - 8475
  • 11
  • [ 109-04-6 ]
  • [ 15889-32-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 17, p. 7410 - 7424
  • 12
  • [ 13331-27-6 ]
  • [ 15889-32-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 17, p. 7410 - 7424
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