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Chemical Structure| 19924-43-7
Chemical Structure| 19924-43-7
Structure of 19924-43-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 19924-43-7 ]

CAS No. :19924-43-7 MDL No. :MFCD00001910
Formula : C9H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :LXKNAUOWEJWGTE-UHFFFAOYSA-N
M.W : 147.17 Pubchem ID :88310
Synonyms :

Calculated chemistry of [ 19924-43-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.46
TPSA : 33.02 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) : -9.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : -3.07
Log Po/w (WLOGP) : 1.76
Log Po/w (MLOGP) : 1.44
Log Po/w (SILICOS-IT) : 2.13
Consensus Log Po/w : 0.82

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.91
Solubility : 1200.0 mg/ml ; 8.13 mol/l
Class : Highly soluble
Log S (Ali) : 2.94
Solubility : 129000.0 mg/ml ; 873.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -2.99
Solubility : 0.149 mg/ml ; 0.00101 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.13

Safety of [ 19924-43-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P310+P330-P405 UN#:3276
Hazard Statements:H301-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 19924-43-7 ]

* 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 [ 19924-43-7 ]
  • Downstream synthetic route of [ 19924-43-7 ]

[ 19924-43-7 ] Synthesis Path-Upstream   1~10

  • 1
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  • [ 22246-12-4 ]
Reference: [1] Archiv der Pharmazie, 1991, vol. 324, # 8, p. 509 - 518
  • 2
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  • [ 2039-67-0 ]
Reference: [1] Archiv der Pharmazie, 1988, vol. 321, # 8, p. 481 - 486
[2] Archiv der Pharmazie, 1991, vol. 324, # 8, p. 509 - 518
[3] Journal of Organic Chemistry, 1982, vol. 47, # 9, p. 1717 - 1721
[4] Journal of Fluorine Chemistry, 1995, vol. 74, # 1, p. 113 - 122
[5] Chemical Communications, 2018, vol. 54, # 11, p. 1323 - 1326
[6] Chemistry - A European Journal, 2012, vol. 18, # 5, p. 1383 - 1400
[7] Chemicke Listy, 1953, vol. 47, p. 1374,1377[8] Chem.Abstr., 1955, p. 1069
  • 3
  • [ 19924-43-7 ]
  • [ 5020-41-7 ]
Reference: [1] Journal of the Chemical Society, 1935, p. 1533,1543
  • 4
  • [ 19924-43-7 ]
  • [ 43050-39-1 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1980, vol. 14, # 3, p. 179 - 184[2] Khimiko-Farmatsevticheskii Zhurnal, 1980, vol. 14, # 3, p. 53 - 59
  • 5
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  • [ 5803-22-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 16, p. 3841 - 3850
  • 6
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  • [ 1798-09-0 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 776 - 794
  • 7
  • [ 19924-43-7 ]
  • [ 25263-44-9 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 200℃; for 0.5 h; Heating / reflux
Stage #3: at 20℃;
Example 1 Synthesis of Exemplified Compound 4 (A) Synthesis of Compound 4-a In a nitrogen atmosphere, 15.5 g of metallic sodium, 200 ml of 1-methyl-2-pyrrolidinone (NMP), and 66.8 g of diphenyldisulfide (PhSSPh) were placed into a flask, and the mixture was refluxed under heating at an outside temperature of 200 C. for 30 minutes. Thereto, added was a solution prepared by dissolving 75 g of (3-methoxyphenyl)acetonitrile in 200 ml of 1-methyl-2-pyrrolidinone, while being refluxed at the same temperature, followed by refluxing under heating at an outside temperature of 200 C. for additional 3 hours. After completion of the reaction,the reaction liquid was cooled to room temperature (r.t.), and 200 ml of hexane and 400 ml of a 0.5M aqueous sodium hydroxide solution were added thereto. The resultant mixture was stirred and transferred into a separatory funnel, and the resultant hexane layer was separated and removed. To the obtained aqueous layer, was added 3M hydrochloric acid to adjust the solution to be acidic, and was subjected to extraction by ethyl acetate. The solution was separated, and an ethyl acetate layer was obtained. The ethyl acetate layer was washed with 1M hydrochloric acid and then a saturated saline solution, dried over anhydrous magnesium sulfate, followed by distilling off the solvent, and being purified by silica gel column chromatography, to thereby obtain 70.4 g (100percent yield) of Compound 4-a. 1H NMR (300 MHz, CDCl3) ? (ppm): 3.73 (2H, s), 6.16 (1H, s), 6.80 to 6.89 (3H, m), 7.20 to 7.30 (1H, m)
98%
Stage #1: With boron tribromide In dichloromethane at 0 - 20℃; for 3 h;
Stage #2: With ethanol; water; sodium hydrogencarbonate In dichloromethane at 0℃;
Intermediate 28. (3-Hydroxyphenyl)acetonitrile; To a solution of (3-methoxyphenyl)acetonitrile (1.89 ml_, 13.59 mmol) in methylene chloride (100 ml_) was added dropwise at 0 0C a 1 M solution of boron tribromide in methylene chloride (65.22 ml_, 65.22 mmol) under nitrogen. The resulting mixture was stirred at room temperature for 3 hours, quenched by slow addition of ethanol (100 ml_) at 0 0C and poured into an excess of saturated sodium bicarbonate solution. The organic layer was separated and washed with ethyl acetate (3 x 100 ml_). The combined organic layers were washed with water (2 x 100 ml_), dried (MgSO4) and the solvents removed under reduced pressure. The title compound was obtained (1.78 g, 98percent) as a brown oil and was used in the next step without further purification.
71%
Stage #1: With boron tribromide In dichloromethane at 0 - 20℃; Inert atmosphere
Stage #2: With water In dichloromethaneCooling with ice
Step ATo a solution of 2-(3-methoxyphenyl)acetonitrile (2 g; 13.59 mmol) in 13 mL of dry DCM) cooled at 0°C under nitrogen atmosphere, a 1M solution of BBr3 in DCM (28.54 mmol; 28.54 mL) is slowly added dropwise. The mixture is stirred at room temperature for 20 hours. The reaction mixture is then poured into ice, water is added and the organic phase is extracted three times with DCM, washed with brine and dried over anhydrous Na2S04. After evaporation, the crude mixture is chromatographed on silica gel using PE/EtAc (80/20) as an eluant, yielding 1.28 g (71percent) of 2-(3-hydroxyphenyl)acetonitrile.
71% With boron tribromide In dichloromethane at 0 - 20℃; for 20 h; Inert atmosphere Step A
To a solution of 2-(3-methoxyphenyl)acetonitrile (2 g; 13.59 mmol) in 13 mL of dry DCM) cooled at 0° C. under nitrogen atmosphere, a 1M solution of BBr3 in DCM (28.54 mmol; 28.54 mL) is slowly added dropwise.
The mixture is stirred at room temperature for 20 hours.
The reaction mixture is then poured into ice, water is added and the organic phase is extracted three times with DCM, washed with brine and dried over anhydrous Na2SO4.
After evaporation, the crude mixture is chromatographed on silica gel using PE/EtAc (80/20) as an eluant, yielding 1.28 g (71percent) of 2-(3-hydroxyphenyl)acetonitrile.

Reference: [1] Patent: US2006/142553, 2006, A1, . Location in patent: Page/Page column 11 - 12
[2] Patent: WO2008/46598, 2008, A1, . Location in patent: Page/Page column 57
[3] Patent: WO2013/651, 2013, A1, . Location in patent: Page/Page column 35; 55
[4] Patent: US2014/88074, 2014, A1, . Location in patent: Paragraph 0286; 0287; 0524; 0525
[5] Patent: US6180627, 2001, B2,
[6] Patent: EP2282736, 2015, B1, . Location in patent: Paragraph 0103
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  • [ 25263-44-9 ]
Reference: [1] Patent: EP997474, 2000, A1,
  • 9
  • [ 19924-43-7 ]
  • [ 3458-98-8 ]
Reference: [1] Journal of Fluorine Chemistry, 1995, vol. 74, # 1, p. 113 - 122
  • 10
  • [ 19924-43-7 ]
  • [ 13292-87-0 ]
  • [ 2039-54-5 ]
Reference: [1] Patent: US4767769, 1988, A,
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