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[ CAS No. 99455-15-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 99455-15-9
Chemical Structure| 99455-15-9
Chemical Structure| 99455-15-9
Structure of 99455-15-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 99455-15-9 ]

CAS No. :99455-15-9 MDL No. :MFCD06738671
Formula : C9H5BrClN Boiling Point : -
Linear Structure Formula :- InChI Key :MOEWRAKNXMILKB-UHFFFAOYSA-N
M.W : 242.50 Pubchem ID :14221034
Synonyms :

Calculated chemistry of [ 99455-15-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.45
TPSA : 12.89 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) : -5.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.4
Log Po/w (XLOGP3) : 3.84
Log Po/w (WLOGP) : 3.65
Log Po/w (MLOGP) : 3.12
Log Po/w (SILICOS-IT) : 3.76
Consensus Log Po/w : 3.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.38
Solubility : 0.0101 mg/ml ; 0.0000417 mol/l
Class : Moderately soluble
Log S (Ali) : -3.81
Solubility : 0.0378 mg/ml ; 0.000156 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.17
Solubility : 0.00162 mg/ml ; 0.00000668 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.79

Safety of [ 99455-15-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 99455-15-9 ]

* 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 [ 99455-15-9 ]
  • Downstream synthetic route of [ 99455-15-9 ]

[ 99455-15-9 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 99465-10-8 ]
  • [ 99455-15-9 ]
YieldReaction ConditionsOperation in experiment
78.8%
Stage #1: With thionyl chloride In dichloromethane; N,N-dimethyl-formamide for 2 h; Heating / reflux
Example 6 Preparation of Compound of Formula (VIII): 7-Bromo-2-chloroquinoline. An inerted reactor equipped with a mechanical stirrer, a reflux condenser, an addition funnel and caustic scrubber was charged with 7-bromo-2-hydroxyquinoline (1.22 Kg, 5.45 mole), dichloromethane (9.706 Kg), and dimethylformamide (0.276 Kg) followed by a slow addition of thionyl chloride (0.973 Kg, 8.17 mole, 1.5 equiv.). The reaction mixture was then gradually heated to reflux. The reflux was continued until solution is achieved (about 2 hours). The reaction mixture was then cooled to 20 to 25°C, and USP purified water (3.663 Kg) was added and stirred. Then to the reactor was gradually added with stirring a solution of potassium carbonate (0.828 Kg) in USP purified water (0.828 Kg). After 15 minutes, the stirring was stopped and the layers were allowed to separate. The pH of aqueous layer was confirmed greater than 7. The dichloromethane solution was separated and washed with USP purified water (3.663 Kg). USP purified water (7.326 Kg) was then added to the dichloromethane solution, and the dichloromethane was distilled off until the product precipitated out of the aqueous layer. The reactor was cooled to 20 to 25°C. The product was filtered and washed USP purified water (2 x 1.22 Kg). The product was dried in a vacuum oven at 40 to 5O0C to obtain 1.154 Kg of desired product. Yield: 78.8percent. NMR: Compatible with product.
Reference: [1] Patent: WO2009/2955, 2008, A1, . Location in patent: Page/Page column 10
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 16, p. 5836 - 5857
  • 2
  • [ 917341-34-5 ]
  • [ 99455-15-9 ]
  • [ 99465-09-5 ]
Reference: [1] Patent: WO2008/71961, 2008, A1, . Location in patent: Page/Page column 103
  • 3
  • [ 163485-85-6 ]
  • [ 99455-15-9 ]
Reference: [1] Patent: US5372813, 1994, A,
  • 4
  • [ 99465-09-5 ]
  • [ 99455-15-9 ]
  • [ 99455-13-7 ]
Reference: [1] Patent: WO2008/71961, 2008, A1, . Location in patent: Page/Page column 103
  • 5
  • [ 99465-10-8 ]
  • [ 99465-09-5 ]
  • [ 99455-15-9 ]
  • [ 99455-13-7 ]
Reference: [1] Patent: WO2006/134378, 2006, A1, . Location in patent: Page/Page column 61-62
  • 6
  • [ 99465-10-8 ]
  • [ 99455-15-9 ]
Reference: [1] European Journal of Medicinal Chemistry, 2010, vol. 45, # 4, p. 1657 - 1662
[2] Bioorganic Chemistry, 2011, vol. 39, # 4, p. 143 - 150
[3] Journal of Medicinal Chemistry, 1988, vol. 31, # 10, p. 2048 - 2056
[4] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 18, p. 2753 - 2758
  • 7
  • [ 591-19-5 ]
  • [ 99455-15-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 10, p. 2048 - 2056
  • 8
  • [ 349426-35-3 ]
  • [ 99455-15-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 18, p. 2753 - 2758
  • 9
  • [ 99465-18-6 ]
  • [ 99455-15-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 10, p. 2048 - 2056
  • 10
  • [ 99465-18-6 ]
  • [ 99455-15-9 ]
  • [ 99455-13-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 14, p. 3130 - 3137
  • 11
  • [ 124-41-4 ]
  • [ 99455-15-9 ]
  • [ 99455-08-0 ]
YieldReaction ConditionsOperation in experiment
98% for 16 h; Reflux This compound was prepared from 7-bromo-2-chloroquinoline(2) in 98percent yield as described for compound 1; Mp 68-69 °C; 1HNMR (300 MHz, CDCl3): δ 8.05 (d, 1H, 1.8 Hz), 7.93 (d, 1H, 8.7 Hz),7.57 (d, 1H, 9.0 Hz), 7.47 (dd, 1H, 8.7 Hz and 1.8 Hz), 6.91 (d, 1H,9.0 Hz), 4.00 (s, 3H); MS (APCI, pos. 30 V) m/z: [M+H]+, 239.06.
Reference: [1] European Journal of Medicinal Chemistry, 2010, vol. 45, # 4, p. 1657 - 1662
[2] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 621 - 631
[3] Journal of Medicinal Chemistry, 1988, vol. 31, # 10, p. 2048 - 2056
  • 12
  • [ 99455-15-9 ]
  • [ 99465-10-8 ]
YieldReaction ConditionsOperation in experiment
93% With hydrogenchloride In 1,4-dioxane; water for 2 h; Reflux A stirred solution mixture of 7-bromo-2-chloroquinoline (5.0 g, 20.6 mmol) in 5 M aqueous hydrochloric acid (133 mL) and 1,4-dioxane (14 mL) was heated at reflux for 2 h. The reaction was cooled and the resulting precipitate was collected by filtration and washed with water to afford the subtitled compound as a colourless solid (4.3 g, 93percent). 1H NMR (400 MHz, DMSO-d6): δ 11.80 (s, 1H), 7.91 (d, 1H), 7.63 (d, 1H), 7.48 (d, 1H), 7.34 (dd, 1H), 6.53 (d, 1H).
93% With hydrogenchloride In 1,4-dioxane; water for 2 h; Reflux A stirred solution mixture of 7-bromo-2-chloroquinoline (5.0 g, 20.6 mmol) in 5 M aqueous hydrochloric acid (133 mL) and 1,4-dioxane (14 mL) was heated at reflux for 2 h.
The reaction was cooled and the resulting precipitate was collected by filtration and washed with water to afford the subtitled compound as a colourless solid (4.3 g, 93percent).
1H NMR (400 MHz, DMSO-d6): δ 11.80 (s, 1H), 7.91 (d, 1H), 7.63 (d, 1H), 7.48 (d, 1H), 7.34 (dd, 1H), 6.53 (d, 1H).
Reference: [1] Patent: US2015/210655, 2015, A1, . Location in patent: Paragraph 0291
[2] Patent: US9522894, 2016, B2, . Location in patent: Page/Page column 34
[3] Patent: WO2008/71961, 2008, A1, . Location in patent: Page/Page column 103-104
[4] Patent: WO2006/134378, 2006, A1, . Location in patent: Page/Page column 61-62
  • 13
  • [ 99455-15-9 ]
  • [ 116632-53-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 9, p. 3958 - 3978
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 16, p. 5836 - 5857
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