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[ CAS No. 185629-32-7 ] {[proInfo.proName]}

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Chemical Structure| 185629-32-7
Chemical Structure| 185629-32-7
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Product Details of [ 185629-32-7 ]

CAS No. :185629-32-7 MDL No. :MFCD08689703
Formula : C8H8FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DOMJYWCXCVFKCA-UHFFFAOYSA-N
M.W : 169.15 Pubchem ID :11182865
Synonyms :

Calculated chemistry of [ 185629-32-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.08
TPSA : 52.32 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) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.72
Log Po/w (XLOGP3) : 1.74
Log Po/w (WLOGP) : 1.62
Log Po/w (MLOGP) : 1.75
Log Po/w (SILICOS-IT) : 1.4
Consensus Log Po/w : 1.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.22
Solubility : 1.01 mg/ml ; 0.00598 mol/l
Class : Soluble
Log S (Ali) : -2.46
Solubility : 0.593 mg/ml ; 0.0035 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.39
Solubility : 0.692 mg/ml ; 0.00409 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 185629-32-7 ]

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 [ 185629-32-7 ]

* 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 [ 185629-32-7 ]
  • Downstream synthetic route of [ 185629-32-7 ]

[ 185629-32-7 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 185629-31-6 ]
  • [ 185629-32-7 ]
YieldReaction ConditionsOperation in experiment
99% With palladium on activated charcoal; hydrogen In ethanol; ethyl acetate at 20℃; for 16 h; A mixture of methyl 3-fluoro-4-nitrobenzoate (2.50 g,12.5 mmol) and Pd/C (300 mg, 10 wtpercent) in 1:1 EtOAc/EtOH (40 mL) was stirred at rt for 16h under 1 atm of H2. The mixture was filtered through Celite and concentrated to give the titlecompound (2.1 g, 99percent) as a beige solid. MS (ES+) C8H8FNO2 requires: 169, found: 170[M+Hj
98% With palladium 10% on activated carbon; hydrogen In methanol; ethyl acetate at 20℃; for 6 h; Methyl 3-fluoro-4-nitrobenzoate (1.0 g, 5.00 mmol) is dissolved in ethyl acetate (5 mL) and methanol (5 mL), followed by adding 10percent Pd/C (150 mg), and the reaction mixture reacts at room temperature for 6 hrs in a hydrogen gas atmosphere, then filtered with siliceousearth, rotated to remove the solvent, so as to obtain a white solid, that is methyl 3-fluoro-4-aminobenzoate, with the yield of 98percent.
Spectrum is : 1H NMR (400 MHz, CDCl3) δ: 7.69(m, 1H), 7.66(m, 1H), 6.76(m, 1H), 4.17(s , 2H), 3.88(s , 3H).
95% With hydrogen In ethanol; ethyl acetate 2. Methyl 4-amino-3-fluorobenzoate[00155]; Methyl 3- fluoro-4-nitrobenzoate (5.18 g, 26.0 mmol) in a 1 : 1 mixture (50 mL) of EtOH and AcOEt with 10percent Pd/C (0.52 g) was hydrogenated on a Parr hydrogenation apparatus at 40 psi. Pd/C was removed by filtration through a pad of Celite.(R). 545. The filtrate was concentrated under vacuum. The residue was diluted with AcOEt, washed with brine, and dried over anhydrous MgSO4. Evaporation of solvent under vacuum gave the title compound (4.17 g, 95percent yield) as a pale solid.
Reference: [1] Patent: WO2018/81276, 2018, A1, . Location in patent: Page/Page column 154
[2] Patent: EP3401315, 2018, A1, . Location in patent: Paragraph 0096; 0097
[3] Patent: WO2007/16392, 2007, A2, . Location in patent: Page/Page column 48
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4345 - 4359
[5] Patent: US2003/232889, 2003, A1, . Location in patent: Page/Page column 15
[6] Patent: WO2012/87519, 2012, A1, . Location in patent: Page/Page column 84; 85
[7] Patent: WO2012/87520, 2012, A1, . Location in patent: Page/Page column 43; 44
  • 2
  • [ 185629-31-6 ]
  • [ 5081-36-7 ]
  • [ 403-21-4 ]
  • [ 185629-32-7 ]
Reference: [1] Patent: US2003/158226, 2003, A1,
  • 3
  • [ 369-25-5 ]
  • [ 185629-32-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 34, p. 6191 - 6194
  • 4
  • [ 403-21-4 ]
  • [ 185629-32-7 ]
Reference: [1] Patent: WO2012/87520, 2012, A1,
[2] Patent: WO2012/87519, 2012, A1,
  • 5
  • [ 185629-32-7 ]
  • [ 924287-65-0 ]
Reference: [1] Patent: WO2012/87520, 2012, A1,
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 24, p. 9960 - 9973
[3] Patent: WO2018/39386, 2018, A1,
[4] Patent: WO2018/81276, 2018, A1,
[5] Patent: WO2012/87519, 2012, A1,
  • 6
  • [ 185629-32-7 ]
  • [ 1123171-91-4 ]
Reference: [1] Patent: US2009/54427, 2009, A1, . Location in patent: Page/Page column 15
  • 7
  • [ 185629-32-7 ]
  • [ 716361-59-0 ]
Reference: [1] Patent: WO2018/110669, 2018, A1,
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