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[ CAS No. 17609-80-2 ] {[proInfo.proName]}

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Chemical Structure| 17609-80-2
Chemical Structure| 17609-80-2
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Product Details of [ 17609-80-2 ]

CAS No. :17609-80-2 MDL No. :MFCD00801116
Formula : C6H6ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :PNLPXABQLXSICH-UHFFFAOYSA-N
M.W : 143.57 Pubchem ID :87184
Synonyms :

Calculated chemistry of [ 17609-80-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 37.88
TPSA : 46.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.17
Log Po/w (XLOGP3) : 1.93
Log Po/w (WLOGP) : 1.64
Log Po/w (MLOGP) : 1.41
Log Po/w (SILICOS-IT) : 1.31
Consensus Log Po/w : 1.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.522 mg/ml ; 0.00364 mol/l
Class : Soluble
Log S (Ali) : -2.53
Solubility : 0.428 mg/ml ; 0.00298 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.06
Solubility : 1.26 mg/ml ; 0.00881 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.1

Safety of [ 17609-80-2 ]

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 [ 17609-80-2 ]

* 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 [ 17609-80-2 ]
  • Downstream synthetic route of [ 17609-80-2 ]

[ 17609-80-2 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 17609-80-2 ]
  • [ 56-81-5 ]
  • [ 18119-24-9 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: With sulfuric acid; boric acid; iron(II) sulfate; nitrobenzene In water at 0 - 150℃; for 22 h;
Stage #2: With potassium carbonate In water
Example 10
Intermediate 10-8-chloro-6-hydroxy-quinoline
In a 500 ml 3-necked flask equipped with a mechanical stirrer and a reflux condenser, added in order were 2.0 g ferrous sulfate, 6.4 g 4-amino, 3-chloro-phenol (generated from 9.0 g of the corresponding commercially available HCl salt), 2.9 m nitrobenzene and a cold solution of 3.0 g boric acid in 16 g of glycerol.
Then, 9 ml of concentrated sulfuric acid was added drop by drop with cooling.
The ice bath was removed and replaced by an oil bath and the mixture was heated cautiously to 120° C. for 2 hrs, then at 150° C. and kept stirring under this temperature for 20 hrs.
The mixture was then cooled and poured on crushed ice and the resulting solution was neutralized to with K2CO3 (saturated solution in water) till exactly pH 5.
The product separated as a light brown solid which was filtered off, washed with water and hexane and dried in a vacuum oven (35° C.) overnight.
The product was purified by dissolving it in a minimal amount of THF, and the solution poured in 20* volume of hexane, giving 7 g (77percent) of the desired product.
77% With sulfuric acid; boric acid; iron(II) sulfate In water; nitrobenzene at 120 - 150℃; for 22 h; In a 500 ml 3-necked flask equipped with a mechanical stirrer and a reflux condenser, added in order were 2.0 g ferrous sulfate, 6.4 g 4-amino, 3-chloro-phenol (generated from 9.0 g of the corresponding commercially available HC1 salt), 2.9 m nitrobenzene and a cold solution of 3.0 g boric acid in 16 g of glycerol. Then, 9 ml of concentrated sulfuric acid was added drop by drop with cooling. The ice bath was removed and replaced by an oil bath and the mixture was heated cautiously to 120°C for 2 hrs, then at 150°C and kept stirring under this temperature for 20 hrs. The mixture was then cooled and poured on crushed ice and the resulting solution was neutralized to with K2C03 (saturated solution in water) till exactly pH 5. The product separated as a light brown solid which was filtered off, washed with water and hexane and dried in a vacuum oven (35°C) overnight. The product was purified by dissolving it in a minimal amount OF THF, and the solution poured in 20X volume of hexane, giving 7 g (77 percent) of the desired product.
Reference: [1] Patent: US2009/54454, 2009, A1, . Location in patent: Page/Page column 15
[2] Patent: WO2004/99191, 2004, A2, . Location in patent: Page 33
  • 2
  • [ 74993-54-7 ]
  • [ 108-43-0 ]
  • [ 17609-80-2 ]
  • [ 56962-00-6 ]
  • [ 28443-50-7 ]
Reference: [1] Journal of the American Chemical Society, 1992, vol. 114, # 25, p. 9795 - 9806
  • 3
  • [ 17609-80-2 ]
  • [ 695-99-8 ]
Reference: [1] Organic Syntheses, 1963, vol. Coll. Vol. IV, p. 148,152 Note 13
[2] Journal of Organic Chemistry, 1952, vol. 17, p. 1047
  • 4
  • [ 74993-54-7 ]
  • [ 108-43-0 ]
  • [ 17609-80-2 ]
  • [ 56962-00-6 ]
  • [ 28443-50-7 ]
Reference: [1] Journal of the American Chemical Society, 1992, vol. 114, # 25, p. 9795 - 9806
  • 5
  • [ 17609-80-2 ]
  • [ 417716-92-8 ]
Reference: [1] Patent: CN105801481, 2016, A,
[2] Patent: CN106632033, 2017, A,
[3] Patent: CN104876864, 2017, B,
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