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[ CAS No. 446-32-2 ] {[proInfo.proName]}

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Chemical Structure| 446-32-2
Chemical Structure| 446-32-2
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Product Details of [ 446-32-2 ]

CAS No. :446-32-2 MDL No. :MFCD00075553
Formula : C7H6FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :LGPVTNAJFDUWLF-UHFFFAOYSA-N
M.W : 155.13 Pubchem ID :2724967
Synonyms :

Calculated chemistry of [ 446-32-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 37.76
TPSA : 63.32 ?2

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) : -6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.64
Log Po/w (XLOGP3) : 0.47
Log Po/w (WLOGP) : 1.53
Log Po/w (MLOGP) : 0.32
Log Po/w (SILICOS-IT) : 0.92
Consensus Log Po/w : 0.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.44
Solubility : 5.69 mg/ml ; 0.0367 mol/l
Class : Very soluble
Log S (Ali) : -1.37
Solubility : 6.64 mg/ml ; 0.0428 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.68
Solubility : 3.27 mg/ml ; 0.0211 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.04

Safety of [ 446-32-2 ]

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 [ 446-32-2 ]

* 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 [ 446-32-2 ]
  • Downstream synthetic route of [ 446-32-2 ]

[ 446-32-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 446-32-2 ]
  • [ 117324-05-7 ]
YieldReaction ConditionsOperation in experiment
94% With thionyl chloride In ethanol A.
Synthesis of ethyl 2-amino-4-fluorobenzoate
To a chilled solution of 2-amino-4-fluorobenzoic acid (1.57 g, 10.1 mmol) in absolute ethanol (20 mL) was added neat thionyl chloride (4.4 mL, 60 mmol).
The reaction mixture was refluxed for 4 days total, with addition of more SOCl2 (8 mL, 110 mmol), then concentrated, diluted with EtOAc, washed with 2N NaOH, dried and concentrated in vacuo to give ethyl 2-amino-4-fluorobenzoate (1.73 g, 94percent).
94% With thionyl chloride In ethanol A.
Synthesis of ethyl 2-amino-4-fluorobenzoate
To a chilled solution of 2-amino-4-fluorobenzoic acid (1.57 g, 10.1 mmol) in absolute ethanol (20 mL) was added neat thionyl chloride (4.4 mL, 60 mmol).
The reaction mixture was refluxed for 4 days total, with addition of more SOCl2 (8 mL, 110 mmol), then concentrated, diluted with EtOAc, washed with 2N NaOH, dried and concentrated in vacuo to give ethyl 2-amino-4-fluorobenzoate (1.73 g, 94percent).
Reference: [1] Patent: US2002/77486, 2002, A1,
[2] Patent: US6906063, 2005, B2,
[3] Patent: EP1380576, 2004, A1, . Location in patent: Page 97
  • 2
  • [ 64-17-5 ]
  • [ 446-32-2 ]
  • [ 117324-05-7 ]
YieldReaction ConditionsOperation in experiment
94% for 96 h; Reflux A. Synthesis of ethyl 2-amino-4-fluorobenzoate (0244) To a chilled solution of 2-amino-4-fluorobenzoic acid (1.57 g, 10.1 mmol) in absolute ethanol (20 mL) was added neat thionyl chloride (4.4 mL, 60 mmol). The reaction mixture was refluxed for 4 days total, with addition of more SOCl2 (8 mL, 110 mmol), then concentrated, diluted with EtOAc, washed with 2N NaOH, dried and concentrated in vacuo to give ethyl 2-amino-4-fluorobenzoate (1.73 g, 94percent).
Reference: [1] Patent: EP2314593, 2016, B1, . Location in patent: Paragraph 0243; 0244
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 17, p. 3772 - 3793
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 10, p. 5803 - 5814
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