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[ CAS No. 222978-02-1 ] {[proInfo.proName]}

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Chemical Structure| 222978-02-1
Chemical Structure| 222978-02-1
Structure of 222978-02-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 222978-02-1 ]

CAS No. :222978-02-1 MDL No. :MFCD08236861
Formula : C8H6FNO Boiling Point : -
Linear Structure Formula :- InChI Key :WLQHJQUGYACADR-UHFFFAOYSA-N
M.W : 151.14 Pubchem ID :11829631
Synonyms :

Calculated chemistry of [ 222978-02-1 ]

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 : 1.0
Molar Refractivity : 37.24
TPSA : 44.02 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 : Yes
Log Kp (skin permeation) : -6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.6
Log Po/w (XLOGP3) : 0.86
Log Po/w (WLOGP) : 1.46
Log Po/w (MLOGP) : 1.28
Log Po/w (SILICOS-IT) : 2.06
Consensus Log Po/w : 1.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.66
Solubility : 3.33 mg/ml ; 0.0221 mol/l
Class : Very soluble
Log S (Ali) : -1.37
Solubility : 6.48 mg/ml ; 0.0429 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.57
Solubility : 0.403 mg/ml ; 0.00267 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 222978-02-1 ]

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

Application In Synthesis of [ 222978-02-1 ]

* 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 [ 222978-02-1 ]
  • Downstream synthetic route of [ 222978-02-1 ]

[ 222978-02-1 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 222978-02-1 ]
  • [ 222978-03-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 10, p. 1257 - 1260
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2973 - 2984
[3] ChemMedChem, 2017, vol. 12, # 23, p. 1953 - 1968
  • 2
  • [ 128-08-5 ]
  • [ 75-18-3 ]
  • [ 222978-02-1 ]
  • [ 222978-03-2 ]
Reference: [1] Patent: US2003/220241, 2003, A1,
[2] Patent: US2003/220241, 2003, A1,
[3] Patent: US2003/220241, 2003, A1,
[4] Patent: US6358985, 2002, B1,
[5] Patent: US6297239, 2001, B1,
[6] Patent: US6316436, 2001, B1,
[7] Patent: US6284755, 2001, B1,
  • 3
  • [ 433939-83-4 ]
  • [ 222978-02-1 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With methanol; ozone In dichloromethane at -78℃; for 0.5 h;
Stage #2: With sodium tetrahydroborate In dichloromethane for 1 h;
Stage #3: With hydrogenchloride In water
Into a cooled solution (-78° C.) of 2-fluoro-4-vinylbenzonitrile (1.3 g, 8.8 mmol; see step (i) above) in 40 mL of CH2Cl2 and 5 mL of methanol was bubbled ozone (50 L/h, 29 g/m3) for 30 min.
Argon was subsequently bubbled through to remove excess ozone.
Sodium borohydride (0.67 g, 0.018 mol) was added and the cooling bath was removed.
The mixture was stirred and allowed to react for 1 h.
The mixture was evaporated and 2M HCl was added.
The mixture was extracted twice with diethyl ether and the combined ether fraction was dried (Na2SO4) and evaporated.
The crude product crystallized. Yield: 1.1 g (81percent).
1H NMR (300 MHz, CDCl3) δ7.59 (m, 1H), 7.3-7.2 (m, 2H), 4.79 (d, 2H), 2.26 (t, 1H)
81%
Stage #1: With ozone In methanol; dichloromethane at -78℃; for 0.5 h;
Stage #2: With sodium tetrahydroborate In methanol; dichloromethane at -78℃; for 1 h;
Into a cooled solution [(-78°C)] of 2-fluoro-4-vinylbenzonitrile (1.3 g, 8.8 mmol; see step (i) above) in 40 mL of [CH2CI2] and 5 mL of methanol was bubbled ozone (50 [L/H,] 29 [G/M3)] for 30 min. Argon was subsequently bubbled through to remove excess ozone. Sodium borohydride (0.67 g, 0.018 mol) was added and the cooling bath was removed. The mixture was stirred and allowed to react for 1 h. The mixture was evaporated and 2M HCI was added. The mixture was extracted twice with diethyl ether and the combined ether fraction was dried [(NA2SO4)] and evaporated. The crude product crystallised. Yield: 1.1 g (81percent). 'H NMR (300 MHz, [CD3) 6] 7.59 (m, 1H), 7.3-7. 2 (m, 2H), 4.79 (d, 2H), 2.26 [(T, I H)]
Reference: [1] Patent: US2004/19033, 2004, A1, . Location in patent: Page/Page column 45
[2] Patent: WO2003/101956, 2003, A1, . Location in patent: Page 127
  • 4
  • [ 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
  • 5
  • [ 176508-81-9 ]
  • [ 222978-02-1 ]
Reference: [1] ChemMedChem, 2017, vol. 12, # 23, p. 1953 - 1968
[2] Patent: WO2017/222951, 2017, A1, . Location in patent: Page/Page column 143
[3] Patent: US2008/119457, 2008, A1,
  • 6
  • [ 557-21-1 ]
  • [ 222978-01-0 ]
  • [ 222978-02-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2973 - 2984
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 10, p. 1257 - 1260
  • 7
  • [ 101048-76-4 ]
  • [ 222978-02-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 12, p. 2388 - 2409
  • 8
  • [ 222978-01-0 ]
  • [ 222978-02-1 ]
Reference: [1] Patent: US2003/220241, 2003, A1,
[2] Patent: US2002/99007, 2002, A1,
[3] Patent: US2002/49217, 2002, A1,
[4] Patent: US6350755, 2002, B1,
[5] Patent: US6413964, 2002, B1,
[6] Patent: US6358985, 2002, B1,
[7] Patent: US6297239, 2001, B1,
  • 9
  • [ 222978-01-0 ]
  • [ 222978-02-1 ]
Reference: [1] Patent: US6562823, 2003, B1,
  • 10
  • [ 77-92-9 ]
  • [ 101048-76-4 ]
  • [ 222978-02-1 ]
Reference: [1] Patent: US6441017, 2002, B1,
  • 11
  • [ 452-74-4 ]
  • [ 222978-02-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2973 - 2984
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 10, p. 1257 - 1260
  • 12
  • [ 153556-42-4 ]
  • [ 222978-02-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2973 - 2984
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 10, p. 1257 - 1260
  • 13
  • [ 85070-67-3 ]
  • [ 222978-02-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 12, p. 2388 - 2409
  • 14
  • [ 440105-58-8 ]
  • [ 222978-02-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 12, p. 2388 - 2409
  • 15
  • [ 222978-02-1 ]
  • [ 101048-76-4 ]
YieldReaction ConditionsOperation in experiment
90% With pyridinium chlorochromate In dichloromethane at 20℃; for 4 h; Example 16b
Preparation of 2-Fluoro-4-formyl-benzonitrile
Pyridinium chlorochromate (7.39 g, 34.27 mmol) is added to a solution of 2-fluoro-4-hydroxymethyl-benzonitrile (5.18 g, 34.27 mmol) in dichloromethane (150 mL), and the mixture is stirred at room temperature for 4 hours.
The reaction mixture is passed through a short silica gel pad, eluding with additional dichloromethane.
The filtrate is concentrated to afford 2-Fluoro-4-formyl-benzonitrile as a white solid (4.6 g, 90percent).
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2973 - 2984
[2] Patent: US2008/119457, 2008, A1, . Location in patent: Page/Page column 51
[3] Patent: US2003/220241, 2003, A1,
[4] Patent: US2003/220241, 2003, A1,
[5] Patent: US2003/87940, 2003, A1,
[6] Patent: US2002/49217, 2002, A1,
[7] Patent: US2002/99007, 2002, A1,
[8] Patent: US6413964, 2002, B1,
[9] Patent: US6350755, 2002, B1,
[10] Patent: US2002/115640, 2002, A1,
[11] Patent: US6297239, 2001, B1,
[12] Patent: US6284755, 2001, B1,
[13] Patent: US6284755, 2001, B1,
  • 16
  • [ 64-17-5 ]
  • [ 1634-04-4 ]
  • [ 222978-02-1 ]
  • [ 101048-76-4 ]
Reference: [1] Patent: US4784471, 1988, A,
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