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[ CAS No. 580-19-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 580-19-8
Chemical Structure| 580-19-8
Chemical Structure| 580-19-8
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Product Details of [ 580-19-8 ]

CAS No. :580-19-8 MDL No. :MFCD01646243
Formula : C9H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :RZAUIOKDXQWSQE-UHFFFAOYSA-N
M.W : 144.17 Pubchem ID :11377
Synonyms :

Calculated chemistry of [ 580-19-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.15
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) : -6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.33
Log Po/w (XLOGP3) : 1.65
Log Po/w (WLOGP) : 1.82
Log Po/w (MLOGP) : 1.19
Log Po/w (SILICOS-IT) : 1.77
Consensus Log Po/w : 1.55

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.45
Solubility : 0.516 mg/ml ; 0.00358 mol/l
Class : Soluble
Log S (Ali) : -2.08
Solubility : 1.2 mg/ml ; 0.00831 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.32
Solubility : 0.0693 mg/ml ; 0.000481 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.23

Safety of [ 580-19-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 580-19-8 ]

* 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 [ 580-19-8 ]
  • Downstream synthetic route of [ 580-19-8 ]

[ 580-19-8 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 580-19-8 ]
  • [ 612-61-3 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 437,44
  • 2
  • [ 580-19-8 ]
  • [ 580-20-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2> 45, p. 238[2] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 176
[3] Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2> 45, p. 238[4] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 176
  • 3
  • [ 613-51-4 ]
  • [ 580-19-8 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogen In methanol for 2 h; Intermediate 53; Preparation of quinolin-7-amine; A mixture of 7-nitroquinoline (0.30 g, 0.0017 mol; Specs, Inc.), 10percent Pd-C (50 mg), and MeOH (20 mL) was stirred under H2 (1 atm) for 2 h. The mixture was filtered and the filtrate was concentrated to give a yellow solid (235 mg, 95percent). LC-MS: 0.33 min, 145.1 (M+1). 1H NMR (DMSO-d6): 8.58 (1H, dd, J=4.4, 1.6 Hz), 8.00 (1H, dd, J=8.0, 1.2 Hz), 7.60 (1H, d, J=8.8 Hz), 7.07 (1H, dd, J=8.0, 4.4 Hz), 6.98 (1H, dd, J=8.8, 2.0 Hz), 6.93 (1H, d, J=2.0 Hz), 5.75 (s, 2H).
95% With hydrogen In methanol for 2 h; Intermediate 16 Preparation of quinolin-7-amine; A mixture of 7-nitroquinoline (0.30 g, 0.0017 mol; Specs, Inc.), 10percent Pd-C (50 mg), and MeOH (20 mL) was stirred under H2 (1 atm) for 2 h. The mixture was filtered and the filtrate was concentrated to give a yellow solid (235 mg, 95percent). LC-MS: 0.33 min, 145.1 (M+1). 1H NMR (DMSO-d6): 8.58 (1H, dd, J=4.4, 1.6 Hz), 8.00 (1H, dd, J=8.0, 1.2 Hz), 7.60 (1H, d, J=8.8 Hz), 7.07 (1H, dd, J=8.0, 4.4 Hz), 6.98 (1H, dd, J=8.8, 2.0 Hz), 6.93 (1H, d, J=2.0 Hz), 5.75 (s, 2H).
62% With palladium on activated charcoal; ammonium formate In methanol 7-aminoquinoline was prepared according to the following reaction in scheme 14.
Reference: [1] Patent: US2006/194801, 2006, A1, . Location in patent: Page/Page column 53
[2] Patent: US2006/205773, 2006, A1, . Location in patent: Page/Page column 29
[3] Steroids, 1995, vol. 60, # 10, p. 693 - 698
[4] Patent: US9522908, 2016, B2, . Location in patent: Paragraph 55; 59
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3497 - 3514
[6] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 177
[7] Chemische Berichte, 1887, vol. 20, p. 3095
[8] Chemische Berichte, 1936, vol. 69, p. 1807,1812
[9] Journal of the American Chemical Society, 1946, vol. 68, p. 149
[10] Yakugaku Zasshi, 1954, vol. 74, p. 1274[11] Chem.Abstr., 1955, p. 3192
[12] Journal of the American Chemical Society, 1940, vol. 62, p. 160
[13] Yakugaku Zasshi, 1947, vol. 67, p. 70[14] Chem.Abstr., 1951, p. 9544
[15] Journal of the American Chemical Society, 1940, vol. 62, p. 160
[16] Yakugaku Zasshi, 1947, vol. 67, p. 70[17] Chem.Abstr., 1951, p. 9544
[18] Chemische Berichte, 1936, vol. 69, p. 1807,1812
[19] Journal of the American Chemical Society, 1946, vol. 68, p. 149
[20] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 17, p. 4533 - 4536
  • 4
  • [ 607-34-1 ]
  • [ 613-51-4 ]
  • [ 580-19-8 ]
  • [ 611-34-7 ]
Reference: [1] Patent: US6750348, 2004, B1, . Location in patent: Page column 41-42
  • 5
  • [ 30450-62-5 ]
  • [ 580-19-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3497 - 3514
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 17, p. 4533 - 4536
[3] Patent: US9522908, 2016, B2,
  • 6
  • [ 179898-22-7 ]
  • [ 580-19-8 ]
  • [ 41148-72-5 ]
Reference: [1] Patent: US5696130, 1997, A,
[2] Patent: US5696133, 1997, A,
  • 7
  • [ 635-46-1 ]
  • [ 580-19-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 17, p. 4533 - 4536
[2] Patent: US9522908, 2016, B2,
  • 8
  • [ 108-45-2 ]
  • [ 56-81-5 ]
  • [ 580-19-8 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 41, p. 21456 - 21464
  • 9
  • [ 99-09-2 ]
  • [ 580-19-8 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 177
[2] Chemische Berichte, 1887, vol. 20, p. 3095
  • 10
  • [ 108-91-8 ]
  • [ 580-19-8 ]
  • [ 65417-78-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 421 - 429
  • 11
  • [ 109-89-7 ]
  • [ 580-19-8 ]
  • [ 36197-73-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 421 - 429
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