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[ CAS No. 13296-04-3 ] {[proInfo.proName]}

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Chemical Structure| 13296-04-3
Chemical Structure| 13296-04-3
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Product Details of [ 13296-04-3 ]

CAS No. :13296-04-3 MDL No. :MFCD00970053
Formula : C11H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :GKVYVZSNXXTOMQ-UHFFFAOYSA-N
M.W :170.21 Pubchem ID :1512654
Synonyms :

Calculated chemistry of [ 13296-04-3 ]

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) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.48
Log Po/w (XLOGP3) : 1.91
Log Po/w (WLOGP) : 2.34
Log Po/w (MLOGP) : 1.47
Log Po/w (SILICOS-IT) : 2.31
Consensus Log Po/w : 1.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.72
Solubility : 0.328 mg/ml ; 0.00192 mol/l
Class : Soluble
Log S (Ali) : -2.35
Solubility : 0.76 mg/ml ; 0.00446 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 : 1.13

Safety of [ 13296-04-3 ]

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 [ 13296-04-3 ]

* 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 [ 13296-04-3 ]
  • Downstream synthetic route of [ 13296-04-3 ]

[ 13296-04-3 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 197435-52-2 ]
  • [ 13296-04-3 ]
YieldReaction ConditionsOperation in experiment
99% With trifluoroacetic acid In dichloromethane at 20℃; for 2 h; Compound 20 (380 mg, 99percent) was obtained after treatment of tert-butyl 4- (pyridin-4-yl)phenylcarbamate (600 mg, 2.2 mmol) with DCM:TFA (1 : 1, 1 mL) for 2 hr at room temperature followed by solvent removal. 4-(Pyridin-4-yl)aniline (20). 1H NMR (400 MHz, d6-DMSO) δ 8.81 (s, 2H), 8.25 (s, 2H), 7.76 (d, J= 8.7 Hz, 2H), 6.87 (m, 2H), 2.09 (s, 2H); MS (ESI) m/z 171 [M+H]+; HRMS (ESI) calcd for CnHn 2 171.0917, found 171.0938.
98% With hydrogenchloride In methanol; water at 80℃; for 4 h; 6 (1.67 g, 6.2 mmol) was dissolved in the mixture of methanol (40 mL) and concentrated hydrochloric acid (8 ml). The solution was stirred at 80 °C for 4 h. All the solvent was then removed under reduced pressure and the residue was washed with sodium carbonate aqueous solution (5percent) and water respectively. 7 (1.03 g, 98percent) was obtained pure enough as a white solid. m.p. 232-234 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.48(d, J = 5.9 Hz, 2H), 7.55(m, 4H), 6.66(d, J = 8.5 Hz, 2H), 5.52(s, 2H). 13C NMR (100 MHz, DMSO-d6) δ 150.22, 149.87, 147.13, 127.42, 123.33, 119.38, 114.01. HRMS Found: [M]+. 270.1371; molecular formula C11H10N2 requires [M]+. 270.1368. IR (KBr): ν 3432, 3311, 3175, 1642, 1585, 1529, 1489, 1412, 1320, 1287, 1226, 1188, 999, 816 cm-1.
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2474 - 2478
[2] Patent: WO2013/112722, 2013, A1, . Location in patent: Page/Page column 45
[3] Dyes and Pigments, 2017, vol. 137, p. 229 - 235
[4] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3542 - 3550
  • 2
  • [ 1692-15-5 ]
  • [ 106-40-1 ]
  • [ 13296-04-3 ]
YieldReaction ConditionsOperation in experiment
72% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water for 3.5 h; Inert atmosphere 4-bromo-aniline 827 mg (4.81 mmol) and 4-boronic acid pyridine 519 mg (4.81 mmol. 1 eq) potassium carbonate(3.99 g 24.88 mmol 6 eq) [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (351.35 mg 481 mmol 6 eq) was placed in a 100 ml two-necked flask and infused with 30 ml (dioxane: water) =3:1) Nitrogen protection, 80 for 3.5 h. After the TLC monitoring reaction is completed, the post-treatment distillation is carried out under reduced pressure to about 10 ml, and the solution is poured into a separating funnel, extracted with dichloromethane for 2-3 times, dried over anhydrous Na 2 SO 4 , filtered, and evaporated to dryness to give a black oily drop. Separation and purification with petroleum ether: ethyl acetate = 6:1 silica gel column chromatography to obtain a pale yellow oily liquid about 590 mg, yield 72percent.
Reference: [1] Patent: CN108467370, 2018, A, . Location in patent: Paragraph 0057; 0058; 0059
[2] Journal of the American Chemical Society, 2012, vol. 134, # 9, p. 4363 - 4372
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 6, p. 1123 - 1134
  • 3
  • [ 59656-60-9 ]
  • [ 13296-04-3 ]
YieldReaction ConditionsOperation in experiment
89% With hydrogenchloride In methanol for 1 h; Inert atmosphere; Reflux A mixture of 4-(4'-acetamidophenyl)pyridine (98) (55 mg, 0.26 mmol) in methanol (2.5 mL) and hydrochloric acid (2.5 mL, 2 M) was heated under reflux for 1 h.
The reaction was quenched with an aqueous solution of sodium hydroxide (20 mL, 1 M), extracted with ethyl acetate (20 mL * 2), dried over anhydrous sodium sulfate, filtered and the solvent removed in vacuo.
Purification by flash chromatography (hexane/ethyl acetate 1:1) afforded 24 as a pale brown solid (39 mg, 0.23 mmol, 89percent). Rf = 0.25 (hexane/ethyl acetate, 1:1); 1H NMR (400 MHz; CDCl3) δH 6.78 (2H, d, J = 8.4 Hz, H-3', H-5'), 7.48-7.51 (4H, m, H-3, H-5, H-2', H-6') and 8.51 (2H, d, J = 4.0 Hz, H-2, H-6); 13C NMR (100 MHz, CDCl3) δC 115.3 (CH), 120.7 (CH), 127.2 (C), 127.9 (CH), 147.8 (C), 148.7 (C) and 149.2 (CH); MS (ESI, 70 eV) m/z 171 (M+, 100percent); Found (M+, 171.0923), C11H11N2 requires 171.0917.
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2220 - 2235
  • 4
  • [ 4282-45-5 ]
  • [ 13296-04-3 ]
YieldReaction ConditionsOperation in experiment
211 mg With palladium 10% on activated carbon; hydrogen In methanol for 20 h; A mixture of 4-(4-nitrophenyl)pyridine (274 mg, 1.37 mmol) and Pd-C (10percent, 80 mg) in MeOH (10 mL) was hydrogenated under balloon H2 for 20 h.
The mixture was then filtered through celite.
The filtrate was concentrated in vacuo to give 4-(pyridin-4-yl)aniline as a solid (211 mg).
Reference: [1] Patent: EP1215208, 2002, A2, . Location in patent: Example C(122)
[2] Chemical Communications, 2017, vol. 53, # 95, p. 12814 - 12817
[3] Journal of Physical Chemistry, 1995, vol. 99, # 18, p. 6876 - 6888
[4] Molecular crystals and liquid crystals, 1980, vol. 62, # 1-2, p. 103 - 114
[5] Patent: US2013/131040, 2013, A1, . Location in patent: Paragraph 0360
[6] RSC Advances, 2016, vol. 6, # 63, p. 58516 - 58520
[7] Patent: CN105949180, 2016, A, . Location in patent: Paragraph 0017-0018
  • 5
  • [ 19524-06-2 ]
  • [ 214360-73-3 ]
  • [ 13296-04-3 ]
Reference: [1] Chemical Communications, 2007, # 45, p. 4752 - 4754
[2] Patent: WO2006/63113, 2006, A2, . Location in patent: Page/Page column 75
  • 6
  • [ 93830-58-1 ]
  • [ 540-37-4 ]
  • [ 13296-04-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 11, p. 4755 - 4763
  • 7
  • [ 1692-15-5 ]
  • [ 13296-04-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3542 - 3550
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2474 - 2478
[3] Patent: US2013/131040, 2013, A1,
[4] Chemical Communications, 2017, vol. 53, # 95, p. 12814 - 12817
  • 8
  • [ 131818-17-2 ]
  • [ 13296-04-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3542 - 3550
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2474 - 2478
[3] Patent: WO2013/112722, 2013, A1,
[4] Dyes and Pigments, 2017, vol. 137, p. 229 - 235
  • 9
  • [ 93830-58-1 ]
  • [ 106-40-1 ]
  • [ 13296-04-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 11, p. 4755 - 4763
  • 10
  • [ 106-40-1 ]
  • [ 13296-04-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2474 - 2478
[2] Patent: WO2013/112722, 2013, A1,
[3] Dyes and Pigments, 2017, vol. 137, p. 229 - 235
  • 11
  • [ 586-78-7 ]
  • [ 13296-04-3 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 63, p. 58516 - 58520
[2] Chemical Communications, 2017, vol. 53, # 95, p. 12814 - 12817
  • 12
  • [ 181219-01-2 ]
  • [ 13296-04-3 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 63, p. 58516 - 58520
  • 13
  • [ 636-98-6 ]
  • [ 13296-04-3 ]
Reference: [1] Patent: US2013/131040, 2013, A1,
  • 14
  • [ 214360-60-8 ]
  • [ 13296-04-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2220 - 2235
  • 15
  • [ 330793-01-6 ]
  • [ 13296-04-3 ]
Reference: [1] Dyes and Pigments, 2017, vol. 137, p. 229 - 235
  • 16
  • [ 321-23-3 ]
  • [ 13296-04-3 ]
Reference: [1] Patent: CN105949180, 2016, A,
  • 17
  • [ 110-86-1 ]
  • [ 13296-04-3 ]
  • [ 113682-56-7 ]
  • [ 113682-55-6 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 7, p. 1415 - 1416[2] Zhurnal Organicheskoi Khimii, 1987, vol. 23, # 7, p. 1573 - 1574
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