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[ CAS No. 577967-89-6 ] {[proInfo.proName]}

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Chemical Structure| 577967-89-6
Chemical Structure| 577967-89-6
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Product Details of [ 577967-89-6 ]

CAS No. :577967-89-6 MDL No. :MFCD12405093
Formula : C9H6ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :XANCOYIVTNZKOE-UHFFFAOYSA-N
M.W : 179.60 Pubchem ID :22132577
Synonyms :

Calculated chemistry of [ 577967-89-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.78
TPSA : 33.12 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) : -5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 2.35
Log Po/w (WLOGP) : 2.59
Log Po/w (MLOGP) : 1.76
Log Po/w (SILICOS-IT) : 2.6
Consensus Log Po/w : 2.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.05
Solubility : 0.16 mg/ml ; 0.00089 mol/l
Class : Soluble
Log S (Ali) : -2.69
Solubility : 0.371 mg/ml ; 0.00206 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.74
Solubility : 0.0327 mg/ml ; 0.000182 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.32

Safety of [ 577967-89-6 ]

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 [ 577967-89-6 ]

* 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 [ 577967-89-6 ]
  • Downstream synthetic route of [ 577967-89-6 ]

[ 577967-89-6 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 13676-02-3 ]
  • [ 577967-89-6 ]
YieldReaction ConditionsOperation in experiment
93% With boron tribromide In dichloromethane at 0 - 20℃; for 15 h; General procedure: To a cooled solution of aryl methyl ether ( 1.0 equiv.) in DCM (10 mL) was added BBr3 (5.0 equiv.) slowly. The resulting mixture was stirred at 0 C and then warmed gradually to room temperature, and. stirred at room temperature for 15 hrs. After the reaction was completed, the reaction was quenched with NaHCO3 solution (50 mL) and extracted with DCM (4 × 10 mL). The combined organic layers were washed with H2O (3 × 10 mL), dried (Na2SO4) and concentrated in vacuo to afford the expected phenols. 2-chloroquinolin-6-ol: DHK-6-71 was prepared using general procedure G. Reaction was performed on a 2 g scale. DHK-6-71 was isolated as yellow solid. (1.72 g. 93percent).
70%
Stage #1: With boron tribromide In dichloromethane at 0 - 25℃; for 2 h;
Stage #2: With ammonium chloride In dichloromethane; water
To a solution of 2-chloro-6-methoxyquinoline (Intermediate 1) (2.00 g, 10.4 mmol) in anhydrous DCM (100 mL) was added BBr3 (6 mL, 62.2 mmol) dropwise at 0°C. The reaction mixture was stirred at 25°C for 2 hours, then quenched with aqueous saturated NH4C1 (50 mL) and filtered. The filtrate was extracted with CH2C12 / MeOH (v / v =10 / 1, 30 mL x2) and the combined organic layers were washed with brine (30 mL), dried over Na2S04, filtered and concentrated under reduced pressure to give 2-chloroquinolin-6-ol (1.30 g, yield 70percent) as yellow solid. 1H NMR (CDC13 300 MHz): δ 7.95 (t, J = 8.1 Hz, 2H), 7.35 (dd, J = 6.0, 3.3 Hz, 2H), 7.13 (d, J = 2.7 Hz, 1H).
70%
Stage #1: With boron tribromide In dichloromethane at 0 - 25℃; for 2 h;
Stage #2: With ammonium chloride In dichloromethane; water at 25℃;
To a solution of 2-chloro-6-methoxyquinoline (Intermediate 1) (2.00 g, 10.4 mmol) in anhydrous DCM (100 mL) was added BBr3 (6 mL, 62.2 mmol) dropwise at 0°C. The reaction mixture was stirred at 25 °C for 2 hours, then quenched with aqueous saturated NH4C1 (50 mL) and filtered. The filtrate was extracted with CH2C12 / MeOH (v / v =10 / 1, 30 mL x2) and the combined organic layers were washed with brine (30 mL), dried over Na2S04, filtered and concentrated under reduced pressure to give 2-chloroquinolin-6-ol (1.30 g, yield 70percent) as yellow solid. *H NMR (CDC13 300 MHz): δ 7.95 (t, / = 8.1 Hz, 2H), 7.35 (dd, / = 6.0, 3.3 Hz, 2H), 7.13 (d, / = 2.7 Hz, 1H).
Reference: [1] Patent: CN102985411, 2016, B, . Location in patent: Paragraph 0906-0908
[2] Patent: WO2012/48181, 2012, A1, . Location in patent: Page/Page column 74
[3] Patent: WO2012/83165, 2012, A1, . Location in patent: Page/Page column 91
[4] ACS Chemical Neuroscience, 2016, vol. 7, # 7, p. 897 - 911
[5] Journal of the American Chemical Society, 1951, vol. 73, p. 4837
  • 2
  • [ 19315-93-6 ]
  • [ 577967-89-6 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With trichlorophosphate In N,N-dimethyl-formamide at 20 - 115℃; for 13 h;
Stage #2: With ammonia In water; N,N-dimethyl-formamide
A solution of 2, 6-quinolinediol 10 (5 g) in POC13 (21 ml) and DMF (3.4 ml) is stirred for 12 h at room temperature, then heated for 1 h at 115 °C. The reaction is poured into water (100 ml) at 0 °C and neutralized with a 32 percent aqueous NH3 solution. The solid obtained by filtration is washed with acetone, and the resulting organic phase is evaporated to give 2-chloro-6-quinolinol 11 as a solid. No further purification is needed. Yield: 98 percent. MS (MH+) : 180.
96% With trichlorophosphate In N,N-dimethyl-formamide at 20 - 70℃; A mixture of 2,6-quinolinediol (10.75 g, 66.7 mmol) was suspended in DMF (24 ml) and phosphorousoxychloride (47.6 g, 333 mmol) was added to the mixture at room-temperature. The temperature increased to 70 °C, the suspension turned into a brown solution that precipitated. Ice (0.5 kg) was added, followed by concentrated ammonia (100 ml). The crystalline product was filtered, washed with water and 11.5 g (96percent) was isolated.
62% at 20℃; for 16 h; Cooling with ice Synthesis of 114
To an N,N-dimethylformamide (20 ml) suspension of 8 (1.16 g, 10 mmol), thionyl chloride (5 g, 42 mmol) was added dropwise under ice cooling and stirring, and the mixture was stirred at room temperature for 16 hours. To the reaction solution, an aqueous saturated sodium hydrogen carbonate solution was added and the solution was extracted with ethyl acetate. The extraction liquid was washed with water and dried, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel flash column chromatography (eluting solvent: ethyl acetate/n-hexane = 1/4) to obtain 114 (1.12 g, 62percent) as a colorless solid. mp 190-191°C
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 142 - 146
[2] Patent: WO2003/93237, 2003, A1, . Location in patent: Page/Page column 51
[3] Patent: WO2009/156396, 2009, A1, . Location in patent: Page/Page column 12
[4] Patent: US2016/244411, 2016, A1, . Location in patent: Paragraph 0263
[5] Patent: EP2634177, 2013, A1, . Location in patent: Paragraph 0307; 0308
[6] Patent: WO2007/90887, 2007, A1, . Location in patent: Page/Page column 14
[7] Patent: US2005/85482, 2005, A1, . Location in patent: Page/Page column 15; 33
[8] Patent: WO2006/52555, 2006, A2, . Location in patent: Page/Page column 30; 63-64
[9] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1678 - 1681
[10] Patent: WO2014/14874, 2014, A1, . Location in patent: Page/Page column 144
[11] Patent: US2015/218102, 2015, A1,
  • 3
  • [ 6563-13-9 ]
  • [ 577967-89-6 ]
Reference: [1] Patent: WO2012/48181, 2012, A1,
[2] Patent: WO2012/83165, 2012, A1,
  • 4
  • [ 5263-87-6 ]
  • [ 577967-89-6 ]
Reference: [1] Patent: WO2012/48181, 2012, A1,
[2] Patent: WO2012/83165, 2012, A1,
  • 5
  • [ 13676-00-1 ]
  • [ 577967-89-6 ]
Reference: [1] Patent: WO2012/48181, 2012, A1,
[2] Patent: WO2012/83165, 2012, A1,
  • 6
  • [ 577967-89-6 ]
  • [ 74-88-4 ]
  • [ 13676-02-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1678 - 1681
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