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[ CAS No. 191014-55-8 ] {[proInfo.proName]}

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Chemical Structure| 191014-55-8
Chemical Structure| 191014-55-8
Structure of 191014-55-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 191014-55-8 ]

CAS No. :191014-55-8 MDL No. :MFCD04116335
Formula : C8H6FNO Boiling Point : -
Linear Structure Formula :- InChI Key :HGBKZVIQHCUHRI-UHFFFAOYSA-N
M.W : 151.14 Pubchem ID :2783329
Synonyms :

Calculated chemistry of [ 191014-55-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.61
TPSA : 33.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.9
Log Po/w (XLOGP3) : 2.53
Log Po/w (WLOGP) : 2.13
Log Po/w (MLOGP) : 1.55
Log Po/w (SILICOS-IT) : 2.21
Consensus Log Po/w : 2.06

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.71
Solubility : 0.296 mg/ml ; 0.00196 mol/l
Class : Soluble
Log S (Ali) : -2.87
Solubility : 0.204 mg/ml ; 0.00135 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.87
Solubility : 0.203 mg/ml ; 0.00134 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.6

Safety of [ 191014-55-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313 UN#:
Hazard Statements:H302-H312-H319-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 191014-55-8 ]

* 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 [ 191014-55-8 ]
  • Downstream synthetic route of [ 191014-55-8 ]

[ 191014-55-8 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 3939-09-1 ]
  • [ 865-33-8 ]
  • [ 191014-55-8 ]
  • [ 94610-82-9 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 27, p. 3776 - 3779
  • 2
  • [ 7677-24-9 ]
  • [ 456-49-5 ]
  • [ 191014-55-8 ]
  • [ 94610-82-9 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 8, p. 2880 - 2883
  • 3
  • [ 191014-55-8 ]
  • [ 186590-01-2 ]
YieldReaction ConditionsOperation in experiment
95% With aluminum (III) chloride In toluene at 130℃; for 18 h; A mixture of intermediate 127, 4-fluoro-2-methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130 C. for 18 hrs. After cooling, ice water (~50 mL) was added and the resulting mixture extracted with ether (20 mLx2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95percent) as a white solid: 1H NMR (DMSO-d6, 300 MHz) ? ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (1H, dd, J=7 Hz, J=8.5 Hz, Ar-H), 11.64 (1H, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) ? ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84, 161.41, 161.58, 163.00, 166.35. HRMS (ESI-) calcd for C7H3NOF (M-H) 136.0199, found 136.0199.
95%
Stage #1: With aluminum (III) chloride In toluene at 130℃; for 18 h;
Stage #2: With water In toluene
A mixture of 4-fluoro-2-methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130° C. for 18 hrs. After cooling, ice water (50 mL)was added and the resulting mixture extracted with ether (20 mL.x.2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95percent) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (1H, dd, J=7 Hz, J=8.5 Hz, Ar-H), 11.64 (1H, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) δ ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84,161.41, 161.58, 163.00, 166.35. HRMS (ESI-) calcd for C7H3NOF (M-H) 136.0199, found 136.0199.
95%
Stage #1: With aluminum (III) chloride In toluene at 130℃; for 18 h;
Stage #2: With water In toluene at 0℃;
4-Fluoro-2-hydroxyben.sum.onitrile. A mixture of intermediate 127, 4-fluoro-2- methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130 °C for 18 hrs. After cooling, ice water (~50 mL)was added and the resulting mixture extracted with ether (20 mL x 2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95percent) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (IH, dd, J = 7 Hz, J = 8.5 Hz, Ar-H), 11.64 (IH, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) δ ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84, 161.41, 161.58, 163.00, 166.35.HRMS (ESI-) calcd for C7H3NOF (M-H) 136.0199, found 136.0199.
Reference: [1] Patent: US2005/267105, 2005, A1, . Location in patent: Page/Page column 67
[2] Patent: US2007/111984, 2007, A1, . Location in patent: Page/Page column 33
[3] Patent: WO2007/64316, 2007, A1, . Location in patent: Page/Page column 153
[4] Patent: WO2007/39172, 2007, A1, . Location in patent: Page/Page column 157-158
[5] Patent: US2008/261979, 2008, A1, . Location in patent: Page/Page column 74
  • 4
  • [ 191014-55-8 ]
  • [ 870563-60-3 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 1, p. 50 - 53
  • 5
  • [ 450-88-4 ]
  • [ 544-92-3 ]
  • [ 191014-55-8 ]
YieldReaction ConditionsOperation in experiment
85% at 180℃; for 5.5 h; To a solution of intermediate 126, 1-bromo-4-fluoro-2-methoxybenzene (9.0 g) in N-methylpyrrolidone (100 mL, Sure Seal; Aldrich) was added CuCN (6.6 g, 73.7 mmol, 1.8 eq.; Aldrich), and the mixture stirred at 180 C. under anhydrous nitrogen for 5.5 hrs. After cooling, 14percent aqueous NH4OH (330 mL) was added and stirring continued for 45 min at room temperature. The mixture was extracted with ether (100 mLx3), and the combined extracts washed sequentially with dilute aqueous NH4OH, dilute HCl and brine, then dried (MgSO4), and concentrated to provide the title compound (5.2 g, Yield 85percent in 2 steps) as a white solid: 1H NMR (CDCl3, 500 MHz) ? ppm: 3.91 (3H, s, OMe), 6.69 (1H, dd, J=2.3 Hz, J=10.5 Hz, Ar-H), 6.72 (1H, dt, J=2.5 Hz, J=J=8.0 Hz, Ar-H), 7.55 (1H, dd, J=6.5 Hz, J=8.5 Hz, Ar-H); 13C NMR (CDCl3, 125.8 Hz) ? ppm: 56.49, 98.16, 100.06, 100.27, 108.31, 108.50, 115.83 135.37, 135.46, 163.25, 163.34 165.47, 167.50. An analytical sample was obtained by trituration with ether: Anal. calcd for C8H6FNO: C, 63.57; H, 4.00; N, 9.26; found: C, 63.36; H, 3.91; N, 9.16.
Reference: [1] Patent: US2005/267105, 2005, A1, . Location in patent: Page/Page column 67
[2] Patent: EP1510516, 2005, A1, . Location in patent: Page/Page column 88
[3] Patent: US2007/111984, 2007, A1, . Location in patent: Page/Page column 32-33
[4] Patent: US2007/129379, 2007, A1, . Location in patent: Page/Page column 26
[5] Patent: WO2007/64316, 2007, A1, . Location in patent: Page/Page column 152
  • 6
  • [ 3939-09-1 ]
  • [ 191014-55-8 ]
Reference: [1] Patent: US2005/20611, 2005, A1, . Location in patent: Page/Page column 39
  • 7
  • [ 557-21-1 ]
  • [ 450-88-4 ]
  • [ 191014-55-8 ]
Reference: [1] Patent: WO2013/28474, 2013, A1, . Location in patent: Page/Page column 69
  • 8
  • [ 748101-41-9 ]
  • [ 450-88-4 ]
  • [ 191014-55-8 ]
Reference: [1] Patent: EP2744499, 2016, B1, . Location in patent: Paragraph 0166
  • 9
  • [ 3939-09-1 ]
  • [ 865-33-8 ]
  • [ 191014-55-8 ]
  • [ 94610-82-9 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 27, p. 3776 - 3779
  • 10
  • [ 147460-41-1 ]
  • [ 191014-55-8 ]
Reference: [1] Patent: WO2013/28474, 2013, A1,
[2] Patent: EP2744499, 2016, B1,
  • 11
  • [ 7677-24-9 ]
  • [ 456-49-5 ]
  • [ 191014-55-8 ]
  • [ 94610-82-9 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 8, p. 2880 - 2883
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