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[ CAS No. 458-52-6 ] {[proInfo.proName]}

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Chemical Structure| 458-52-6
Chemical Structure| 458-52-6
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Product Details of [ 458-52-6 ]

CAS No. :458-52-6 MDL No. :MFCD00047827
Formula : C7H8FNO Boiling Point : -
Linear Structure Formula :- InChI Key :YWUVOJJHVFLNJA-UHFFFAOYSA-N
M.W :141.14 Pubchem ID :3756383
Synonyms :

Calculated chemistry of [ 458-52-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.3
TPSA : 35.25 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) : -6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 1.41
Log Po/w (WLOGP) : 1.84
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 1.53
Consensus Log Po/w : 1.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.98
Solubility : 1.47 mg/ml ; 0.0104 mol/l
Class : Very soluble
Log S (Ali) : -1.75
Solubility : 2.48 mg/ml ; 0.0176 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.42
Solubility : 0.538 mg/ml ; 0.00381 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 458-52-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 458-52-6 ]

* 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 [ 458-52-6 ]
  • Downstream synthetic route of [ 458-52-6 ]

[ 458-52-6 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 4755-50-4 ]
  • [ 458-52-6 ]
  • [ 10205-71-7 ]
Reference: [1] Synthesis, 2010, # 12, p. 1983 - 1988
  • 2
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  • [ 458-50-4 ]
Reference: [1] Journal of the Chemical Society, 1931, p. 981
  • 3
  • [ 446-38-8 ]
  • [ 458-52-6 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogen In ethanol b) 2-fluoro-4-(methoxy)aniline; A solution of 3-fluoro-4-nitrophenyl methyl ether (28.1 g, 164 mmol) in ethanol (200 mL) was hydrogenated with palladium on charcoal. The reaction mixture was filtered through Kieselguhr and evaporated under vacuum to afford the product as an oil (22.8 g, 98percent); MS (+ve ion electrospray) m/z 141 (MH+).
97% With hydrogen In methanol at 20℃; for 1 h; To a stirred solution of 2-fluoro-4-methoxy-l -nitrobenzene (2.76 g, 16.13 mmol) in methanol (5O mL) at room temperature under nitrogen was added 10percent palladium on carbon (276 mg). Hydrogen gas was bubbled through the reaction mixture for 1 h, whereupon the suspension was filtered through a short pad of celite. The filtrate was evaporated and the resulting red oil was triturated with petroleum ether. The resulting orange solid was filtered off and dried to give 2-fluoro-4-methoxyaniline, (2.2 g, 97 percent).
73% With palladium on activated charcoal In ethyl acetate at 20℃; for 1 h; 2-fluoro-4-methoxy-nitrobenzene (0.5 g, 2.9 mmol) was dissolved in ethyl acetate (10 mL) was added palladium on carbon (50 mg), stirred at room temperature for 1 hour. The reaction mixture was filtered, the filtrate was concentrated to give 2-fluoro-4-methoxyaniline (8B), a brown solid (0.3 g, 73percent yield) of the title compound.
41 g With palladium on activated charcoal; hydrogen In methanol at 20℃; for 4 h; A solution of Compound 74a (50g) and Pd/C (lOg) in MeOH (lOOml) under H2 was stirred at room temperature for 4hrs. After filtered, the filtrate was concentrated under reduced pressure togive 41g Compound 74b.

Reference: [1] Patent: WO2006/2047, 2006, A2, . Location in patent: Page/Page column 69-70
[2] Patent: WO2009/84970, 2009, A1, . Location in patent: Page/Page column 71
[3] Patent: CN104395312, 2016, B, . Location in patent: Paragraph 0689; 0690-0694
[4] Journal of the Chemical Society, 1931, p. 981
[5] Journal of the Chemical Society, 1940, p. 1268,1270
[6] Australian Journal of Chemistry, 1972, vol. 25, p. 2621 - 2629
[7] Heterocycles, 1992, vol. 34, # 12, p. 2301 - 2311
[8] Patent: US5262390, 1993, A,
[9] Patent: US5399543, 1995, A,
[10] Patent: US2004/204427, 2004, A1, . Location in patent: Page/Page column 20
[11] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 12, p. 3526 - 3529
[12] Patent: WO2015/3658, 2015, A1, . Location in patent: Page/Page column 54
  • 4
  • [ 217314-31-3 ]
  • [ 458-52-6 ]
Reference: [1] Synthesis, 1998, # 11, p. 1599 - 1603
[2] Organic Syntheses, 2002, vol. 78, p. 63 - 63
  • 5
  • [ 209353-23-1 ]
  • [ 458-52-6 ]
Reference: [1] Helvetica Chimica Acta, 1998, vol. 81, # 6, p. 1088 - 1094
  • 6
  • [ 394-41-2 ]
  • [ 458-52-6 ]
Reference: [1] Heterocycles, 1992, vol. 34, # 12, p. 2301 - 2311
[2] Journal of the Chemical Society, 1940, p. 1268,1270
[3] Australian Journal of Chemistry, 1972, vol. 25, p. 2621 - 2629
  • 7
  • [ 372-20-3 ]
  • [ 458-52-6 ]
Reference: [1] Heterocycles, 1992, vol. 34, # 12, p. 2301 - 2311
  • 8
  • [ 29632-74-4 ]
  • [ 458-52-6 ]
Reference: [1] Organic Syntheses, 2002, vol. 78, p. 63 - 63
  • 9
  • [ 104-94-9 ]
  • [ 458-52-6 ]
  • [ 366-99-4 ]
  • [ 363-47-3 ]
Reference: [1] Journal of Fluorine Chemistry, 2005, vol. 126, # 4, p. 661 - 667
  • 10
  • [ 104-94-9 ]
  • [ 458-52-6 ]
  • [ 366-99-4 ]
  • [ 363-47-3 ]
Reference: [1] Journal of Fluorine Chemistry, 2005, vol. 126, # 4, p. 661 - 667
  • 11
  • [ 104-94-9 ]
  • [ 458-52-6 ]
  • [ 366-99-4 ]
  • [ 363-47-3 ]
Reference: [1] Journal of Fluorine Chemistry, 2005, vol. 126, # 4, p. 661 - 667
  • 12
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  • [ 501-29-1 ]
Reference: [1] Journal of the Chemical Society, 1931, p. 981
  • 13
  • [ 458-52-6 ]
  • [ 940298-93-1 ]
Reference: [1] Journal of Fluorine Chemistry, 2006, vol. 127, # 9, p. 1256 - 1260
  • 14
  • [ 458-52-6 ]
  • [ 1421373-65-0 ]
Reference: [1] Patent: CN104910049, 2016, B,
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