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[ CAS No. 19910-33-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 19910-33-9
Chemical Structure| 19910-33-9
Chemical Structure| 19910-33-9
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Product Details of [ 19910-33-9 ]

CAS No. :19910-33-9 MDL No. :MFCD00012106
Formula : C9H9NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :RBSRRICSXWXMRC-UHFFFAOYSA-N
M.W : 195.17 Pubchem ID :89244
Synonyms :

Calculated chemistry of [ 19910-33-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.62
TPSA : 83.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.23
Log Po/w (XLOGP3) : 1.76
Log Po/w (WLOGP) : 1.78
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : -0.42
Consensus Log Po/w : 1.05

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.28
Solubility : 1.03 mg/ml ; 0.00527 mol/l
Class : Soluble
Log S (Ali) : -3.12
Solubility : 0.147 mg/ml ; 0.000753 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.59
Solubility : 5.01 mg/ml ; 0.0256 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.08

Safety of [ 19910-33-9 ]

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 [ 19910-33-9 ]

* 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 [ 19910-33-9 ]
  • Downstream synthetic route of [ 19910-33-9 ]

[ 19910-33-9 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 19910-33-9 ]
  • [ 100-27-6 ]
Reference: [1] Journal of the American Chemical Society, 1988, vol. 110, # 13, p. 4336 - 4345
  • 2
  • [ 50712-64-6 ]
  • [ 19910-33-9 ]
YieldReaction ConditionsOperation in experiment
78.8% With water; sodium hydroxide In ethanol at 20℃; for 2 h; To a solution of compound 39.2 (4.5 g, 20.17 mmol, 1.0 eq) in ethanol (40 ml) was added NaOH (1.614 g, 40.35 mmol, 2 eq.) and water (10 ml). Reaction was stirred at room temperature for 2 hours. After completion of the reaction, solvent was evaporated under reduced pressure and water was added. Dilute HCl was added to acidify the reaction mixture. The product was extracted with ethyl acetate. Organic layers were combined and dried over Na2SO4 and concentrated under reduced pressure to obtain crude which was purified by column chromatography to furnish 39.3 (3.1 g, 78.8percent). MS (ES): m/z 195.17 [M+H]+.
Reference: [1] Patent: US2016/251376, 2016, A1, . Location in patent: Paragraph 0625; 0628; 0629
  • 3
  • [ 50712-63-5 ]
  • [ 19910-33-9 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogenchloride In water at 20℃; for 14 h; Heating / reflux a)
2-(4-Amino-phenyl)-propionic acid (1)
2-(4-nitro-phenyl)-propionitrile (6.03 g) is added to conc. hydrochloric acid (50 ml) at room temperature.
The reaction mixture is refluxed for 14 h.
The mixture is cooled to room temperature.
The mixture is extracted with dichloromethane.
The extracts are washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo.
2-(4-nitro-phenyl)-propionitrile (6.03 g) is added to conc. hydrochloric acid (50 ml) at room temperature. The reaction mixture is refluxed for 14 h. The mixture is cooled to room temperature. The mixture is extracted with dichloromethane.The extracts are washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo.Pale white solid, yield: 99percent.; 2-(4-nitro-phenyl)-propionitrile (6.03 g) is added to conc. hydrochloric acid (50 ml) at room temperature. The reaction mixture is refluxed for 14 h. The mixture is cooled to room temperature. The mixture is extracted with dichloromethane. The extracts are washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo.Pale yellow solid, yield: quantitative.; 2-(4-nitro-phenyl)-propionitrile (6.03 g) is added to conc. hydrochloric acid (50 ml) at room temperature. The reaction mixture is refluxed for 14 h. The mixture is cooled to room temperature. The mixture is extracted with dichloromethane. The extracts are washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo.Pale yellow solid, yield: quantitative.
Reference: [1] Patent: US2009/156590, 2009, A1, . Location in patent: Page/Page column 62; 63; 64; 65
[2] Tetrahedron Letters, 2010, vol. 51, # 40, p. 5246 - 5251
[3] Chemische Berichte, 1916, vol. 49, p. 2280
[4] Arzneimittel-Forschung/Drug Research, 1973, vol. 23, # 8, p. 1090 - 1100
  • 4
  • [ 50415-69-5 ]
  • [ 19910-33-9 ]
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 10, p. 1704 - 1712
[2] Patent: US4476315, 1984, A,
[3] Organic Letters, 2011, vol. 13, # 16, p. 4240 - 4243
  • 5
  • [ 17639-93-9 ]
  • [ 50415-69-5 ]
  • [ 7440-44-0 ]
  • [ 19910-33-9 ]
Reference: [1] Patent: US4476315, 1984, A,
  • 6
  • [ 61881-49-0 ]
  • [ 19910-33-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1983, vol. 26, # 2, p. 222 - 226
  • 7
  • [ 104-03-0 ]
  • [ 19910-33-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 11, p. 1704 - 1711
  • 8
  • [ 50434-36-1 ]
  • [ 19910-33-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 11, p. 1704 - 1711
  • 9
  • [ 492-37-5 ]
  • [ 19910-33-9 ]
  • [ 77656-96-3 ]
  • [ 21762-10-7 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 4, p. 952 - 958
  • 10
  • [ 5445-26-1 ]
  • [ 19910-33-9 ]
Reference: [1] Patent: US2016/251376, 2016, A1,
  • 11
  • [ 1823-91-2 ]
  • [ 19910-33-9 ]
Reference: [1] Chemische Berichte, 1916, vol. 49, p. 2280
[2] Arzneimittel-Forschung/Drug Research, 1973, vol. 23, # 8, p. 1090 - 1100
  • 12
  • [ 492-37-5 ]
  • [ 19910-33-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1885, vol. 227, p. 274
  • 13
  • [ 20461-79-4 ]
  • [ 100-51-6 ]
  • [ 19910-33-9 ]
Reference: [1] Chemische Berichte, 1952, vol. 85, p. 168,171
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