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[ CAS No. 52671-64-4 ] {[proInfo.proName]}

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Chemical Structure| 52671-64-4
Chemical Structure| 52671-64-4
Structure of 52671-64-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 52671-64-4 ]

CAS No. :52671-64-4 MDL No. :MFCD00143110
Formula : C6H7Cl2NO Boiling Point : -
Linear Structure Formula :- InChI Key :RFJVQGMBFQGZPV-UHFFFAOYSA-N
M.W : 180.03 Pubchem ID :12598190
Synonyms :

Calculated chemistry of [ 52671-64-4 ]

Physicochemical Properties

Num. heavy atoms : 10
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 : 44.84
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 : No
Log Kp (skin permeation) : -5.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.73
Log Po/w (WLOGP) : 2.44
Log Po/w (MLOGP) : 1.75
Log Po/w (SILICOS-IT) : 1.31
Consensus Log Po/w : 1.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.12
Solubility : 0.137 mg/ml ; 0.000758 mol/l
Class : Soluble
Log S (Ali) : -3.36
Solubility : 0.0794 mg/ml ; 0.000441 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.06
Solubility : 1.59 mg/ml ; 0.00881 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.16

Safety of [ 52671-64-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52671-64-4 ]

* 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 [ 52671-64-4 ]
  • Downstream synthetic route of [ 52671-64-4 ]

[ 52671-64-4 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 52671-64-4 ]
  • [ 56-81-5 ]
  • [ 18119-24-9 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: With sulfuric acid; boric acid; iron(II) sulfate In nitrobenzene at 120 - 150℃; for 22 h;
Stage #2: With potassium carbonate In water; nitrobenzene
Step 4:
8-Chloro-6-hydroxyquinoline
In a 500 mL 3-necked flask equipped with a mechanical stirrer, a reflux condenser, were added in order ferrous sulfate (2.0 g), 4-amino-3-chlorophenol hydrochloride (6.4 g, commercially available), nitrobenzene (2.9 mL) and a solution of boric acid (3.0 g) in glycerol (16 g).
Then concentrated sulfuric acid (9 mL) 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 hours, then at 150° C. and kept stirring under this temperature for 20 hours.
After cooling, the reaction was poured on crushed ice and the resulting solution was neutralized with K2CO3.
The product separated as a light brown solid that was filtered off, washed with water and hexanes and dried in a vacuum oven (35° C.) overnight giving 7 g (77percent) of the desired product. MS (ES) m/z (relative intensity): 180 (M++-H, 100).
77%
Stage #1: at 0 - 150℃; for 22 h;
Stage #2: With potassium carbonate In water
In a 500 ml 3-necked flask equipped with a mechanical stirrer, a reflux condenser, were added in order ferrous sulfate (2.0 g), 4-amino-3-chlorophenol hydrochloride (6.4 g, commercially available), nitrobenzene (2.9 mL) and a solution of boric acid (3.0 g) in glycerol (16 g).
Then concentrated sulfuric acid (9 mL) 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 hours, then at 150° C. and kept stirring under this temperature for 20 hours.
After cooling, the reaction was poured on crushed ice and the resulting solution was neutralized with K2CO3.
The product separated as a light brown solid that was filtered off, washed with water and hexanes and dried in a vacuum oven (35° C.) overnight giving 7 g (77percent) of the desired product. MS (ES) m/z (relative intensity): 180 (M++-H, 100).
Reference: [1] Patent: US2007/299083, 2007, A1, . Location in patent: Page/Page column 14
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 4066 - 4084
[3] Patent: US2007/27160, 2007, A1, . Location in patent: Page/Page column 43
  • 2
  • [ 52671-64-4 ]
  • [ 98-95-3 ]
  • [ 18119-24-9 ]
YieldReaction ConditionsOperation in experiment
77% With sulfuric acid; boric acid; iron(II) sulfate In glycerol at 0 - 150℃; for 22 h; Step 4: 8-Chloro-6-hydroxyquinoline In a 500 mL 3-necked flask equipped with a mechanical stirrer, a reflux condenser, were added in order ferrous sulfate (2.0 g), 4-amino-3-chlorophenol hydrochloride (6.4 g, commercially available), nitrobenzene (2.9 mL) and a solution of boric acid (3.0 g) in glycerol (16 g). Then concentrated sulfuric acid (9 mL) 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 1200C for 2 hours, then at 1500C and kept stirring under this temperature for 20 hours. After cooling, the reaction was poured on crushed ice and the resulting solution was neutralized with K2CO3. The product separated as a light brown solid that was filtered off, washed with water and hexanes and dried in a vacuum oven (35°C) overnight giving 7 g (77 percent) of the desired product. MS (ES) m/z (relative intensity): 180 (M++-H, 100).
Reference: [1] Patent: WO2007/146116, 2007, A2, . Location in patent: Page/Page column 28
  • 3
  • [ 52671-64-4 ]
  • [ 796851-15-5 ]
Reference: [1] Patent: WO2007/146116, 2007, A2,
  • 4
  • [ 52671-64-4 ]
  • [ 74-88-4 ]
  • [ 29242-84-0 ]
YieldReaction ConditionsOperation in experiment
41%
Stage #1: With potassium <i>tert</i>-butylate; potassium carbonate In acetone at 20℃;
Stage #2: at 20℃; for 2 h;
To a suspension of 4-amino-3-chlorophenol hydrochloride (500 mg, 2.7 MMOL) in acetone (5 mL), at r. t. , under N2, were added K2CO3 (138 mg, 1 eq) and t-BuOK (311 mg, 1 eq). Mel was then added (173pL, 1eq.). The reaction mixture was stirred at r. t. for 2 hr. CH2CI2 (10 mL) was added and the reaction quenched with H20 (5 mL). The phases were separated and the aqueous layer was extracted with CH2CI2 (5 mL). The combined organic extracts were dried over anh. NA2SO4, the solids were filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash chromatography (silica gel, CH2Cl2 100percent) to give the title compound (180 mg, 41 percent). NMR (APOS;H, DMSO): 8 6.81 (d, 1H), 6.72 (s, 1H), 6.68 (d, 1H), 4.81 (s, 2H), 3.63 (s, 3H).
Reference: [1] Patent: WO2004/62665, 2004, A1, . Location in patent: Page/Page column 38
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