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Product Details of [ 56962-11-9 ]

CAS No. :56962-11-9 MDL No. :MFCD00052184
Formula : C7H5ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZMOMCILMBYEGLD-UHFFFAOYSA-N
M.W : 156.57 Pubchem ID :185363
Synonyms :

Calculated chemistry of [ 56962-11-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.86
TPSA : 37.3 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) : -6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.24
Log Po/w (XLOGP3) : 0.97
Log Po/w (WLOGP) : 1.86
Log Po/w (MLOGP) : 1.39
Log Po/w (SILICOS-IT) : 2.14
Consensus Log Po/w : 1.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.8
Solubility : 2.48 mg/ml ; 0.0159 mol/l
Class : Very soluble
Log S (Ali) : -1.34
Solubility : 7.14 mg/ml ; 0.0456 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.37
Solubility : 0.663 mg/ml ; 0.00424 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.09

Safety of [ 56962-11-9 ]

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 [ 56962-11-9 ]

* 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 [ 56962-11-9 ]
  • Downstream synthetic route of [ 56962-11-9 ]

[ 56962-11-9 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 108-43-0 ]
  • [ 76-03-9 ]
  • [ 2420-26-0 ]
  • [ 56962-11-9 ]
Reference: [1] Journal of the Chemical Society, 1933, p. 496,498
  • 2
  • [ 3336-16-1 ]
  • [ 56962-11-9 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With diisobutylaluminium hydride In tetrahydrofuran; hexane at -78 - 20℃; for 19 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water at 0℃;
Diisobutylaluminium hydride (1M in hexane, 240 mL, 240 mmol) was added to a solution of 2-chloro-4-hydroxybenzonitrile (15 g, 97.7 mmol) in tetrahydrofuran (200 mL), cooled to -78° C., and the mixture was stirred at this temperature for 1 hour then at room temperature for 18 hours.
The mixture was then cooled to 0° C. and 1M hydrochloric acid (80 mL) was added dropwise.
The reaction mixture was diluted with water (200 mL) and filtered, washing through with ethyl acetate (*2).
The layers of the filtrate were separated and the organic solution was dried over magnesium sulfate and concentrated in vacuo.
Trituration of the residue with dichloromethane afforded the title compound as a solid in 84percent yield, 12.92 g.
Reference: [1] Patent: US2006/35922, 2006, A1, . Location in patent: Page/Page column 31
[2] Patent: WO2014/69963, 2014, A1, . Location in patent: Paragraph 885-886
[3] Patent: WO2007/136116, 2007, A2, . Location in patent: Page/Page column 83-85
  • 3
  • [ 108-43-0 ]
  • [ 67-66-3 ]
  • [ 56962-11-9 ]
YieldReaction ConditionsOperation in experiment
16%
Stage #1: for 4.33333 h; Heating / reflux
Stage #2: With hydrogenchloride In chloroform; water
lntermediate 14; 2-Chloro-4-hydroxybenzaldehyde. 3-Ghlorophenol (CAS 108-43-0)(49.2 g, 0.380 mol), calcium hydroxide (122.0 g), and sodium carbonate (139.4 g) were suspended in water (872 mL). Chloroform (90.6 g, 0.760 mol) was added for 80 min, and the mixture was refluxed under vigorous stirring for 3 h. The reaction mixture was cooled on ice bath. Concentrated HCI (385 mL) and chloroform (300 mL) were added. The aqueous layer was discarded. The organic one was dried with anhydrous Na2SO4 (50 g) and evaporated in vacuo. The residue was purified by chromatography (silica gel 63-100 μm, 600 g, CCI4--> CHCI3-* CHCI3ZEtOAc 93:7). Fractions containing the product were combined, evaporated, and coevaporated with dioxane to give the title compound (9.77 g, 0.062 mol, 16percent) as a white powder. 1H NMR data (DMSO-d6): 11.06 (s, 1H, COIH); 10.14 (s, 1 H, OH); 7.75 (d, 1 H, J=8.5 Hz, Ar-H); 6.92 (d, 1 H, J=2 Hz, Ar-H); 6.85 (d.d., 1 H, J^δ.5 Hz, J2=2 Hz, Ar-H).
15.3% for 4.33333 h; Inert atmosphere; Reflux To a solution of compound B7 (150 g, 1.17 mol), calcium hydroxide (375 g, 5.07 mol), and sodium carbonate (420 g, 3.96 mol) in 1.5 L of water was added chloroform (270 g, 2.29 mol) for 80 min, and the mixture was refluxed under N2 atmosphere for 3 h. The reaction mixture was cooled on an ice bath. 1 L of cone. aq. HCI and 1 L of chloroform were added. The mixture was shaken and after phase separation the aqueous layer was discarded. The organic one was dried with Na2SO4, concentrated and purified by chromatography on silica gel (eluent: PE/EtOAc = 10/1) to give 28 g of compound B8 as a white solid (Yield: 15.3percent).
15.3% With sodium carbonate; calcium hydroxide In water for 3 h; Reflux; Inert atmosphere Synthesis of Compound B8: [Show Image] To a solution of compound B7 (150 g, 1.17 mol), calcium hydroxide (375 g, 5.07 mol), and sodium carbonate (420 g, 3.96 mol) in 1.5 L of water was added chloroform (270 g, 2.29 mol) for 80 min, and the mixture was refluxed under N2 atmosphere for 3 h. The reaction mixture was cooled on an ice bath. 1 L of conc. aq. HCl and 1 L of chloroform were added. The mixture was shaken and after phase separation the aqueous layer was discarded. The organic one was dried with Na2SO4, concentrated and purified by chromatography on silica gel (eluent: PE/EtOAc = 10/1) to give 28 g of compound B8 as a white solid (Yield: 15.3percent).
Reference: [1] Patent: WO2006/136924, 2006, A1, . Location in patent: Page/Page column 98
[2] Patent: WO2011/20615, 2011, A1, . Location in patent: Page/Page column 45; 47; 48
[3] Patent: EP2289883, 2011, A1, . Location in patent: Page/Page column 19
[4] Journal of Chemical & Engineering Data, 1983, vol. 28, # 1, p. 139 - 141
[5] Journal of Organic Chemistry, 1964, vol. 29, p. 2693 - 2698
  • 4
  • [ 874-42-0 ]
  • [ 56962-11-9 ]
Reference: [1] Patent: DE942808, 1953, ,
  • 5
  • [ 108-43-0 ]
  • [ 74-90-8 ]
  • [ 56962-11-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1907, vol. 357, p. 373
  • 6
  • [ 121-86-8 ]
  • [ 56962-11-9 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 1741
  • 7
  • [ 108-43-0 ]
  • [ 76-03-9 ]
  • [ 2420-26-0 ]
  • [ 56962-11-9 ]
Reference: [1] Journal of the Chemical Society, 1933, p. 496,498
  • 8
  • [ 56962-11-9 ]
  • [ 74-88-4 ]
  • [ 54439-75-7 ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate In water; N,N-dimethyl-formamide Reference Example 20
-chloro-4-methoxybenzaldehyde
To a solution of 2-chloro-4-hydroxybenzaldehyde (2 g, 12.8 mmol) in N,N-dimethylformamide (25 mL) were added potassium carbonate (3.46 g, 25 mmol) and methyl iodide (large excess) and the mixture was stirred at room temperature for 18 h.
Water was added to the reaction mixture and the mixture was extracted with ethyl acetate.
The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate.
The solvent was evaporated under reduced pressure to give an almost pure title compound (1.55 g, 70percent).
1H-NMR (δ ppm, CDCl3): 3.89 (3H, s), 6.84-6.95 (2H, m), 7.90 (1H, d, J=8.8 Hz), 10.33 (1H, s)
Reference: [1] Patent: EP1223170, 2002, A1,
[2] Patent: EP1813611, 2007, A1, . Location in patent: Page/Page column 23
[3] Patent: EP1354884, 2003, A1, . Location in patent: Page/Page column 232
[4] Patent: US2005/250796, 2005, A1, . Location in patent: Page/Page column 12
[5] Patent: WO2011/20615, 2011, A1, . Location in patent: Page/Page column 69
[6] Patent: WO2018/89449, 2018, A1, . Location in patent: Page/Page column 163-166
  • 9
  • [ 56962-11-9 ]
  • [ 79213-60-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2553 - 2570
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