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[ CAS No. 94444-96-9 ] {[proInfo.proName]}

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Chemical Structure| 94444-96-9
Chemical Structure| 94444-96-9
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Product Details of [ 94444-96-9 ]

CAS No. :94444-96-9 MDL No. :MFCD07781657
Formula : C8H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :GZWWDKIVVTXLFL-UHFFFAOYSA-N
M.W : 148.16 Pubchem ID :13346860
Synonyms :

Calculated chemistry of [ 94444-96-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.59
TPSA : 37.91 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) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.2
Log Po/w (XLOGP3) : 1.66
Log Po/w (WLOGP) : 1.57
Log Po/w (MLOGP) : 0.84
Log Po/w (SILICOS-IT) : 2.02
Consensus Log Po/w : 1.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.34
Solubility : 0.671 mg/ml ; 0.00453 mol/l
Class : Soluble
Log S (Ali) : -2.07
Solubility : 1.26 mg/ml ; 0.00851 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.02
Solubility : 0.142 mg/ml ; 0.000959 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 94444-96-9 ]

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 [ 94444-96-9 ]

* 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 [ 94444-96-9 ]
  • Downstream synthetic route of [ 94444-96-9 ]

[ 94444-96-9 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 94444-96-9 ]
  • [ 15579-15-4 ]
YieldReaction ConditionsOperation in experiment
71% With boron tribromide In dichloromethane at 20℃; for 10 h; A methylene chloride solution of boron tribromide (18.5 ml, 18.5 mmol) was added to a solution of 5-methoxy-1H-indazole (1.24 g, 8.40 mmol) in methylene chloride (84 ml) at 0°C and stirred at room temperature for 10 hours. Then, water was poured into the reaction solution in an ice-water bath, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol = 96/4) to obtain 1H-indazol-5-ol (877 mg, 71percent).1H-NMR (DMSO-d6) δ; 6.88 (1H, dd, J=8.8, 2.2Hz), 6.96 (1H, d, J=2.2Hz), 7.34 (1H, d, J=8.8Hz), 7.84 (1H, s).
Reference: [1] Patent: EP1403255, 2004, A1, . Location in patent: Page 44
  • 2
  • [ 102-50-1 ]
  • [ 94444-96-9 ]
YieldReaction ConditionsOperation in experiment
18% With acetic acid; sodium nitrite In water at 20℃; A solution of sodium nitrite (3.38 g, 49.0 mmol) in water (8.1 ml) was added to a solution of 4-methoxy-2-methylaniline (6.69 g, 48.8 mmol) in acetic acid (350 ml) in an ice-water bath while maintaining the temperature at 25°C or lower, and stirred overnight at room temperature. Then, the reaction solution was poured into water and extracted with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol = 9/1) to obtain 5-methoxy-1H-indazole (1.30 g, 18percent).1H-NMR (DMSO-d6) δ; 3.76 (3H, s), 6.98 (1H, dd, J=8.8, 1.8Hz), 7.15 (1H, d, J=1.8Hz), 7.42 (1H, d, J=8.8Hz), 7.93 (1H, s), 12.89 (1H, brs).
Reference: [1] Patent: EP1403255, 2004, A1, . Location in patent: Page 44
[2] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 1, p. 309 - 315
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 23, p. 5293 - 5297
[4] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 9, p. 1153 - 1156
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2410 - 2414
  • 3
  • [ 31601-41-9 ]
  • [ 94444-96-9 ]
Reference: [1] Yakugaku Zasshi, 1959, vol. 79, p. 997,1001[2] Chem.Abstr., 1960, p. 5719
[3] Patent: WO2006/52555, 2006, A2, . Location in patent: Page/Page column 33; 74
  • 4
  • [ 672-13-9 ]
  • [ 94444-96-9 ]
Reference: [1] Heterocycles, 2018, vol. 96, # 1, p. 74 - 85
  • 5
  • [ 105728-90-3 ]
  • [ 94444-96-9 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 8166 - 8172
  • 6
  • [ 459-60-9 ]
  • [ 94444-96-9 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 8, p. 1769 - 1771
  • 7
  • [ 420-37-1 ]
  • [ 94444-96-9 ]
  • [ 541539-88-2 ]
YieldReaction ConditionsOperation in experiment
59% at 20℃; for 3 h; To a solution of 5-methoxy-indazole (1.0 g, 6.7 mmol) in ethyl acetate (10 ml) was added BF40(CH3)3(1.3 g, 8.9 mmol). The solution was stirred at rt for 3 h. Sat. NaHC03aq. (10 ml) was added and extracted with ethyl acetate (20 ml). Organics were dried over Na2S04, concentrated, and purified by flash chromatography on silica gel (PE /EA = 2/1) to afford 0.64 g (59percent) of the title compound as a yellow solid. [M+H] Calc'd for C9H10N2O, 163; Found, 163.
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 10, p. 4093 - 4095
[2] Patent: WO2016/44138, 2016, A1, . Location in patent: Paragraph 00116
[3] Patent: WO2007/3419, 2007, A1, . Location in patent: Page/Page column 69-72
  • 8
  • [ 94444-96-9 ]
  • [ 2533-69-9 ]
  • [ 541539-88-2 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 13, p. 1661 - 1663
  • 9
  • [ 94444-96-9 ]
  • [ 885519-30-2 ]
Reference: [1] Synthesis, 2011, # 16, p. 2651 - 2663
[2] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 23, p. 5293 - 5297
  • 10
  • [ 94444-96-9 ]
  • [ 478834-25-2 ]
Reference: [1] Patent: EP1403255, 2004, A1,
  • 11
  • [ 94444-96-9 ]
  • [ 78299-75-9 ]
Reference: [1] Patent: EP1403255, 2004, A1,
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