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[ CAS No. 19883-57-9 ] {[proInfo.proName]}

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Chemical Structure| 19883-57-9
Chemical Structure| 19883-57-9
Structure of 19883-57-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 19883-57-9 ]

CAS No. :19883-57-9 MDL No. :
Formula : C8H8FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JKFYKCYQEWQPTM-ZETCQYMHSA-N
M.W : 169.15 Pubchem ID :853015
Synonyms :

Calculated chemistry of [ 19883-57-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.65
TPSA : 63.32 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) : -8.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.1
Log Po/w (XLOGP3) : -1.6
Log Po/w (WLOGP) : 1.01
Log Po/w (MLOGP) : -1.0
Log Po/w (SILICOS-IT) : 0.95
Consensus Log Po/w : 0.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.12
Solubility : 129.0 mg/ml ; 0.761 mol/l
Class : Very soluble
Log S (Ali) : 0.78
Solubility : 1020.0 mg/ml ; 6.02 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.73
Solubility : 3.13 mg/ml ; 0.0185 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 19883-57-9 ]

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 [ 19883-57-9 ]

* 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 [ 19883-57-9 ]
  • Downstream synthetic route of [ 19883-57-9 ]

[ 19883-57-9 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 144744-29-6 ]
  • [ 19883-57-9 ]
  • [ 93939-74-3 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 25, p. 6914 - 6920
  • 2
  • [ 7292-73-1 ]
  • [ 19883-57-9 ]
  • [ 93939-74-3 ]
Reference: [1] Tetrahedron Asymmetry, 2000, vol. 11, # 6, p. 1343 - 1351
[2] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3327 - 3332
  • 3
  • [ 1428149-40-9 ]
  • [ 19883-57-9 ]
  • [ 93939-74-3 ]
Reference: [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3327 - 3332
  • 4
  • [ 56464-70-1 ]
  • [ 133721-87-6 ]
  • [ 459-57-4 ]
  • [ 19883-57-9 ]
  • [ 93939-74-3 ]
Reference: [1] Tetrahedron Asymmetry, 2004, vol. 15, # 18, p. 2793 - 2796
  • 5
  • [ 56464-70-1 ]
  • [ 19883-57-9 ]
  • [ 93939-74-3 ]
Reference: [1] Patent: EP2319919, 2015, B1, . Location in patent: Paragraph 0495
[2] Patent: EP2319919, 2015, B1, . Location in patent: Paragraph 0495
  • 6
  • [ 19883-57-9 ]
  • [ 174770-74-2 ]
YieldReaction ConditionsOperation in experiment
82% With sodium hydroxide In tetrahydrofuran; water a
(R)-2-Amino-2-(4-fluorophenyl)ethanol
To a stirred 1.0M solution of lithium aluminium hydride in THF (23.5 ml, 23.5 mmol), cooled to 0° C. under Ar, was added portionwise over 1 h 45 min solid (-)-4-fluoro-D-α-phenylglycine (1.98 g, 11.7 mmol).
The reaction mixture was then stirred at room temperature overnight before carefully adding water (0.89 ml), then 4N NaOH solution (0.89 ml) and then water (2.68 ml).
The mixture was stirred for a few minutes, then filtered, and the filtrate was evaporated in vacuo.
Flash chromatography of the residue (silica gel, dichloromethane-methanol-ammonia, 90:10:1) gave 1.499 g (82percent) of the title compound as a white solid; δH (250 MHz, CDCl3) 3.52 (1H, dd, J=10.7 and 8.2 Hz), 3.71 (1H, dd, J=10.7 and 4.4 Hz), 4.06 (1H, dd, J=8.1 and 4.4 Hz), 6.99-7.08 (2H, m), 7.28-7.34 (2H, m).
82% With sodium hydroxide In tetrahydrofuran; water 1.
(R)-2-Amino-2-(4-fluorophenyl)ethanol
To a stirred 1.0M solution of lithium aluminium hydride in THF (23.5 ml, 23.5 mmol), cooled to 0° C. under Ar, was added portionwise over 1 h 45 min solid (-)-4-fluoro-D-α-phenylglycine (1.98 g, 11.7 mmol).
The reaction mixture was then stirred at room temperature overnight before carefully adding water (0.89 ml), then 4N NaOH solution (0.89 ml) and then water (2.68 ml).
The mixture was stirred for a few minutes, then filtered, and the filtrate was evaporated in vacuo.
Flash chromatography of the residue (silica gel, dichloromethane/methanol/ammonia, 90:10:1) gave 1.499 g (82percent) of the title compound as a white solid: δH (250 MHz, CDCl3) 3.52 (1H, dd, J=10.7 and 8.2 Hz), 3.71 (1H, dd, J=10.7 and 4.4 Hz), 4.06 (1H, dd, J=8.1 and 4.4 Hz), 6.99-7.08 (2H, m), 7.28-7.34 (2H, m).
Reference: [1] Patent: US5952369, 1999, A,
[2] Patent: US5998440, 1999, A,
[3] Patent: US5854268, 1998, A,
  • 7
  • [ 24424-99-5 ]
  • [ 19883-57-9 ]
  • [ 142186-36-5 ]
Reference: [1] Patent: EP1187812, 2005, B1, . Location in patent: Page/Page column 27
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1991 - 1995
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 63 - 67
[4] Patent: WO2017/131221, 2017, A1, . Location in patent: Page/Page column 66; 67
  • 8
  • [ 19883-57-9 ]
  • [ 224434-01-9 ]
Reference: [1] Patent: WO2006/44412, 2006, A1, . Location in patent: Page/Page column 51-52
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