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[ CAS No. 81224-16-0 ] {[proInfo.proName]}

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Chemical Structure| 81224-16-0
Chemical Structure| 81224-16-0
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Product Details of [ 81224-16-0 ]

CAS No. :81224-16-0 MDL No. :MFCD04037872
Formula : C9H8BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :WWKHWWGUJPWWDF-UHFFFAOYSA-N
M.W : 226.07 Pubchem ID :3695499
Synonyms :

Calculated chemistry of [ 81224-16-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.49
TPSA : 25.02 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) : -5.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.15
Log Po/w (XLOGP3) : 2.71
Log Po/w (WLOGP) : 2.94
Log Po/w (MLOGP) : 1.95
Log Po/w (SILICOS-IT) : 3.17
Consensus Log Po/w : 2.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.44
Solubility : 0.0825 mg/ml ; 0.000365 mol/l
Class : Soluble
Log S (Ali) : -2.89
Solubility : 0.292 mg/ml ; 0.00129 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.27
Solubility : 0.0121 mg/ml ; 0.0000537 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 81224-16-0 ]

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

Application In Synthesis of [ 81224-16-0 ]

* 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 [ 81224-16-0 ]
  • Downstream synthetic route of [ 81224-16-0 ]

[ 81224-16-0 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 59557-92-5 ]
  • [ 107-14-2 ]
  • [ 107-06-2 ]
  • [ 81224-16-0 ]
YieldReaction ConditionsOperation in experiment
24% With hydrogenchloride; sodium borohydrid; boron trichloride In 1,4-dioxane; dichloromethane; water (a)
4-Methoxy-7-bromoindole.
2-Bromo-5-methoxy-aniline (4.4 g, 21.8 mmol) was added dropwise to a solution of boron trichloride in methylene chloride (1.0 M, 24 mL, 24 mmol) cooled with ice water.
The reaction mixture was warmed to room temperature, stirred for 30 min, and chloroacetonitrile (4.01 mL, 26.2 mmol) and aluminum chloride (4.01 g, 24.0 mmol) were added, followed by 1,2-dichloroethane (28.5 mL).
The reaction mixture was heated to 70° C. to distill off methylene chloride, and then heated to reflux for 24 hrs.
After cooling to 0-5° C., the mixture was treated with 2.5 M HCl (38.4 mL) carefully, and then heated to 80° C. for 1 h until all solids dissolved.
The aqueous layer was separated, extracted with methylene chloride and the combined extracts washed with water and brine, dried (sodium sulfate) and evaporated to a yellow solid, which was used without further purification.
The crude product was taken into dioxane (37 mL) and water (4.2 mL), and treated with sodium borohydride (0.91 g, 24.0 mmol) in portions.
After stirring at room temperature for 30 min, all the starting material was consumed and the reaction mixture was then heated to reflux for 14 hrs.
After cooling to room temperature, the mixture was treated with concentrated HCl, and extracted with ethyl acetate.
The organic extract was washed with water and brine; dried (sodium sulfate), and concentrated.
Column chromatography on silica gel (hexanes/ethyl acetate) gave 4-methoxyl-7-bromoindole (1.2 g, 24percent).
1H NMR (400 MHz, CDCl3) 3.94 (s, 3H), 6.44 (d, J=8.21 Hz, 1H), 6.73 (m, 1H), 7.17 (t, J=2.74 Hz, 1H), 7.22~7.26 (m, 1H), 8.32 (br, 1H); MS (ES, m/z): C9H8BrNO: 227.99 (M+(79Br)+1), 230.0(M+(81Br)+1).
Reference: [1] Patent: US2004/48915, 2004, A1,
  • 2
  • [ 81224-15-9 ]
  • [ 81224-16-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1373 - 1377
  • 3
  • [ 5344-78-5 ]
  • [ 1826-67-1 ]
  • [ 81224-16-0 ]
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 26, p. 3376 - 3378
[2] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1223 - 1226
  • 4
  • [ 25016-01-7 ]
  • [ 81224-16-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1373 - 1377
  • 5
  • [ 81224-14-8 ]
  • [ 81224-16-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1373 - 1377
  • 6
  • [ 81224-45-5 ]
  • [ 81224-16-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1373 - 1377
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