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[ CAS No. 268734-34-5 ] {[proInfo.proName]}

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Chemical Structure| 268734-34-5
Chemical Structure| 268734-34-5
Structure of 268734-34-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 268734-34-5 ]

CAS No. :268734-34-5 MDL No. :MFCD09264509
Formula : C9H6FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :AHJLHWRWDRCIKO-UHFFFAOYSA-N
M.W : 179.15 Pubchem ID :17965941
Synonyms :

Calculated chemistry of [ 268734-34-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.39
TPSA : 50.09 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) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.89
Log Po/w (XLOGP3) : 1.59
Log Po/w (WLOGP) : 1.9
Log Po/w (MLOGP) : 1.71
Log Po/w (SILICOS-IT) : 2.11
Consensus Log Po/w : 1.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.16
Solubility : 1.23 mg/ml ; 0.00689 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 1.0 mg/ml ; 0.00558 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.84
Solubility : 0.261 mg/ml ; 0.00146 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 268734-34-5 ]

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

Application In Synthesis of [ 268734-34-5 ]

* 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 [ 268734-34-5 ]
  • Downstream synthetic route of [ 268734-34-5 ]

[ 268734-34-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 268734-34-5 ]
  • [ 222978-03-2 ]
Reference: [1] ChemMedChem, 2017, vol. 12, # 23, p. 1953 - 1968
  • 2
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 105942-08-3 ]
  • [ 268734-34-5 ]
YieldReaction ConditionsOperation in experiment
59% With triethylamine; triphenylphosphine In acetonitrile at 50℃; A mixture OF4-BROMO-2-FLUORO-BENZONITRILE (4.00 g, 20.0 mmol), ET3N (3.94 g, 38.9 mmol), palladium (II) acetate (314 mg, 1.40 MMOL), triphenylphosphine (214 mg, 0.816 mmol) in 4: 1 CH3CN/MeOH (50 mL) is purged with a stream of nitrogen for 15 min in a sealed tube equipped with gas inlet/outlet valves. The reaction is flushed with carbon monoxide (3 X 60 psi), releasing the pressure between each addition. The reaction is left under an atmosphere of carbon monoxide (60 psi) and heated to-50 C overnight. The pressure is released and the reaction mixture is filtered through a SINTERED-GLASS FUNNEL containing diatomaceous earth, washing with MEOH (20 mL). The reaction residue is subjected to flash chromatography (silica gel, 9: 1 Hex/EtOAc) to afford the sub-title compound (2.13 g, 59percent) as a white solid. Rf 0.33 (4 : 1 HEX/ETOAC). mp 61-62 C. 'H NMR (300 MHz, CDC13) B 3.97 (s, 3H), 7.72 (DD, J = 6.2, 8.0 HZ, 1H), 7.86 (dd, J= 1.3, 9.2 Hz, 1H), 7.93 (dd, J= 1.3, 8.0 Hz, 1H).
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 18, p. 7102 - 7107
[2] Patent: WO2004/67529, 2004, A1, . Location in patent: Page 173
  • 3
  • [ 67-56-1 ]
  • [ 176508-81-9 ]
  • [ 268734-34-5 ]
YieldReaction ConditionsOperation in experiment
87% at 20℃; Step 1: methyl-4-cyano-3-fluorobenzoate4-Cyano-3-fluorobenzoic acid (1 g; 6.06 mmol) was suspended in MeOH (10 mL) and 1-(3- dimethyl aminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (1.39 g; 7.27 mmol; 1 .20 eq.) and 4-dimethylaminopyridine (70 mg; 0.61 mmol; 0.10 eq.) were added. The mixture was stirred at RT overnight. <n="98"/>Solvents were concentrated and the resulting mixture was taken up into EtOAc (20 ml_) and washed with 0.1 N HCI solution (10 ml_), 0.1 N NaOH solution (10 ml.) and brine (2x10 ml_), dried over MgSO4 and evaporated. The title product was isolated as an off-white solid (0.95 g; 87percent). 1H-NMR (DMSO-d6, 300MHz) δ 8.16 (dd, J = 6.40 Hz, J = 7.91 Hz, 1 H), 8.02 (dd, J = 1.50 Hz, J = 9.80 Hz, 1 H), 7.97 (dd. J = 1.50 Hz, J = 7.91 , 1 H), 3.95 (s, 3H). GC/MS Rt 3.10 min: 179 (M+H)+. HPLC (Method A) Rt 3.17 min (Purity: 87percent).
Reference: [1] Patent: WO2009/80663, 2009, A1, . Location in patent: Page/Page column 96-97
[2] Patent: WO2009/43889, 2009, A2, . Location in patent: Page/Page column 111-112
  • 4
  • [ 105942-08-3 ]
  • [ 268734-34-5 ]
Reference: [1] Patent: US2002/115640, 2002, A1,
[2] Patent: US2003/87940, 2003, A1,
  • 5
  • [ 77-78-1 ]
  • [ 176508-81-9 ]
  • [ 268734-34-5 ]
Reference: [1] ChemMedChem, 2017, vol. 12, # 23, p. 1953 - 1968
[2] Patent: US2008/119457, 2008, A1, . Location in patent: Page/Page column 51
  • 6
  • [ 268734-34-5 ]
  • [ 222978-02-1 ]
Reference: [1] ChemMedChem, 2017, vol. 12, # 23, p. 1953 - 1968
[2] Patent: US2003/87940, 2003, A1,
[3] Patent: US2002/115640, 2002, A1,
[4] Patent: US2008/119457, 2008, A1, . Location in patent: Page/Page column 51
  • 7
  • [ 268734-34-5 ]
  • [ 101048-76-4 ]
Reference: [1] Patent: US2008/119457, 2008, A1,
  • 8
  • [ 268734-34-5 ]
  • [ 176508-81-9 ]
Reference: [1] Organic letters, 2003, vol. 5, # 1, p. 7 - 10
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