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[ CAS No. 873055-09-5 ] {[proInfo.proName]}

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Chemical Structure| 873055-09-5
Chemical Structure| 873055-09-5
Structure of 873055-09-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 873055-09-5 ]

CAS No. :873055-09-5 MDL No. :MFCD22689954
Formula : C12H14N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :COQNCAZGNLRPHM-UHFFFAOYSA-N
M.W : 218.25 Pubchem ID :57470196
Synonyms :

Calculated chemistry of [ 873055-09-5 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.33
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 66.39
TPSA : 61.61 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) : -5.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.22
Log Po/w (XLOGP3) : 3.59
Log Po/w (WLOGP) : 3.37
Log Po/w (MLOGP) : 2.39
Log Po/w (SILICOS-IT) : 1.49
Consensus Log Po/w : 2.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.74
Solubility : 0.0398 mg/ml ; 0.000182 mol/l
Class : Soluble
Log S (Ali) : -4.57
Solubility : 0.00587 mg/ml ; 0.0000269 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.88
Solubility : 0.0286 mg/ml ; 0.000131 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.08

Safety of [ 873055-09-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 873055-09-5 ]

* 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.

  • Downstream synthetic route of [ 873055-09-5 ]

[ 873055-09-5 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 873055-08-4 ]
  • [ 873055-09-5 ]
YieldReaction ConditionsOperation in experiment
80% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20.0℃; for 2.5h;Heating / reflux; To a solution of 2-tert-butyl-6-nitroindoline (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ (6.9 g, 30 mmol) at room temperature. The mixture was heated at reflux for 2.5 h before being filtered and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%). 1H NMR (300 MHz, CDCl3) delta 8.30 (br. s, 1H), 8.29 (s, 1H), 8.00 (dd, J=2.1, 8.7 Hz, 1H), 7.53 (d, J=9.3 Hz, 1H), 6.38 (s, 1H), 1.43 (s, 9H).
80% With bunazosin; In 1,4-dioxane; 2-tert-Butyl-6-nitro-1H-indole To a solution of 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ at room temperature. After refluxing for 2.5 h, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%).
80% With bunazosin; In 1,4-dioxane; 2-tert-Butyl-6-nitro-1H-indole To a solution of 2-tert-butyl-6-nitroindoline (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ (6.9 g, 30 mmol) at room temperature. The mixture was heated at reflux for 2.5 h before being filtered and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%). 1H NMR (300 MHz, CDCl3) delta 8.30 (br. s, 1H), 8.29 (s, 1H), 8.00 (dd, J=2.1, 8.7 Hz, 1H), 7.53 (d, J=9.3 Hz, 1H), 6.38 (s, 1H), 1.43 (s, 9H).
80% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20.0℃; for 2.5h;Reflux; To a solution of 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ at room temperature. After refluxing for 2.5 h, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%).
80% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; for 2.5h;Reflux; To a solution of 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ at room temperature. After refluxing for 2.5 h, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%).

  • 2
  • [ 873055-09-5 ]
  • 2-tert-butyl-1H-indol-6-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With hydrogen;nickel; In methanol; at 20.0℃; under 760.051 Torr; for 3.0h; To a solution of <strong>[873055-09-5]2-tert-butyl-6-nitro-1H-indole</strong> (1.3 g, 6.0 mmol) in MeOH (10 mL) was added Raney Nickel (0.2 g). The mixture was hydrogenated under 1 atm of hydrogen at room temperature for 3 h. The reaction mixture was filtered and the filtrate was concentrated. The residue washed with petroleum ether to give 2-tert-butyl-1H-indol-6-amine (1.0 g, 89%). 1H NMR (300 MHz, DMSO-d6) delta 10.19 (s, 1H), 6.99 (d, J=8.1 Hz, 1H), 6.46 (s, 1H), 6.25 (dd, J=1.8, 8.1 Hz, 1H), 5.79 (d, J=1.8 Hz, 1H), 4.52 (s, 2H), 1.24 (s, 9H); MS (ESI) m/e (M+H+) 189.1.
89% In methanol; B-6; 2-tert-Butyl-1H-indol-6-ylamine To a solution of <strong>[873055-09-5]2-tert-butyl-6-nitro-1H-indole</strong> (1.3 g, 6.0 mmol) in MeOH (10 mL) was added Raney Ni (0.2 g). The mixture was stirred at room temperature under H2 (1 atm) for 3 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was washed with petroleum ether to give 2-tert-butyl-1H-indol-6-ylamine (B-6) (1.0 g, 89%). 1H NMR (DMSO-d6) delta 10.19 (s, 1H), 6.99 (d, J=8.1 Hz, 1H), 6.46 (s, 1H), 6.25 (dd, J=1.8, 8.1 Hz, 1H), 5.79 (d, J=1.8 Hz, 1H), 4.52 (s, 2H), 1.24 (s, 9H); ESI-MS 189.1 m/z (MH+).
89% With hydrogen;Raney Ni; In methanol; at 20.0℃; for 3.0h; To a solution of <strong>[873055-09-5]2-tert-butyl-6-nitro-1H-indole</strong> (1.3 g, 6.0 mmol) in MeOH (10 mL) was added Raney Ni (0.2 g). The mixture was stirred at room temperature under H2 (1 atm) for 3 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was washed with petroleum ether to give 2-tert-butyl-1H-indol-6-ylamine (B-6) (1.0 g, 89%). 1H NMR (DMSO-d6) delta 10.19 (s, 1H), 6.99 (d, J=8.1 Hz, 1H), 6.46 (s, 1H), 6.25 (dd, J=1.8, 8.1 Hz, 1H), 5.79 (d, J=1.8 Hz, 1H), 4.52 (s, 2H), 1.24 (s, 9H); ESI-MS 189.1 ink (MH+).
89% With Raney Ni; In methanol; at 20.0℃; under 760.051 Torr; for 3.0h; To a solution of <strong>[873055-09-5]2-tert-butyl-6-nitro-1H-indole</strong> (1.3 g, 6.0 mmol) in MeOH (10 mL) was added Raney Ni (0.2 g). The mixture was stirred at room temperature under H2 (1 atm) for 3 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was washed with petroleum ether to give 2-tert-butyl-1H-indol-6-ylamine (B-6) (1.0 g, 89%). 1H NMR (DMSO-d6) delta 10.19 (s, 1H), 6.99 (d, J=8.1 Hz, 1H), 6.46 (s, 1H), 6.25 (dd, J=1.8, 8.1 Hz, 1H), 5.79 (d, J=1.8 Hz, 1H), 4.52 (s, 2H), 1.24 (s, 9H); ESI-MS 189.1 m/z (MH+).

  • 6
  • raney Nickel [ No CAS ]
  • [ 873055-09-5 ]
  • 2-tert-butyl-1H-indol-6-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With hydrogen; In methanol; 2-tert-Butyl-1H-indol-6-amine To a solution of <strong>[873055-09-5]2-tert-butyl-6-nitro-1H-indole</strong> (1.3 g, 6.0 mmol) in MeOH (10 mL) was added Raney Nickel (0.2 g). The mixture was hydrogenated under 1 atm of hydrogen at room temperature for 3 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was washed with petroleum ether to give 2-tert-butyl-1H-indol-6-amine (1.0 g, 89%). 1H NMR (300 MHz, DMSO-d6) delta 10.19 (s, 1H), 6.99 (d, J=8.1 Hz, 1H), 6.46 (s, 1H), 6.25 (dd, J=1.8, 8.1 Hz, 1H), 5.79 (d, J=1.8 Hz, 1H), 4.52 (s, 2H), 1.24 (s, 9H); MS (ESI) m/e (M+H+) 189.1.
  • 9
  • [ 99-65-0 ]
  • [ 873055-09-5 ]
  • 10
  • [ 1388183-59-2 ]
  • [ 873055-09-5 ]
  • 11
  • [ 1388183-49-0 ]
  • [ 873055-09-5 ]
  • 12
  • [ 13547-70-1 ]
  • [ 873055-09-5 ]
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