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[ CAS No. 459-22-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 459-22-3
Chemical Structure| 459-22-3
Chemical Structure| 459-22-3
Structure of 459-22-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 459-22-3 ]

CAS No. :459-22-3 MDL No. :MFCD00001917
Formula : C8H6FN Boiling Point : -
Linear Structure Formula :- InChI Key :JHQBLYITVCBGTO-UHFFFAOYSA-N
M.W : 135.14 Pubchem ID :68016
Synonyms :

Calculated chemistry of [ 459-22-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.92
TPSA : 23.79 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) : -5.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.62
Log Po/w (XLOGP3) : 1.94
Log Po/w (WLOGP) : 2.31
Log Po/w (MLOGP) : 2.21
Log Po/w (SILICOS-IT) : 2.55
Consensus Log Po/w : 2.13

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.28
Solubility : 0.712 mg/ml ; 0.00527 mol/l
Class : Soluble
Log S (Ali) : -2.06
Solubility : 1.17 mg/ml ; 0.00863 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.13
Solubility : 0.099 mg/ml ; 0.000733 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.06

Safety of [ 459-22-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 459-22-3 ]

* 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 [ 459-22-3 ]
  • Downstream synthetic route of [ 459-22-3 ]

[ 459-22-3 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 383-63-1 ]
  • [ 459-22-3 ]
  • [ 3108-23-4 ]
Reference: [1] Patent: WO2015/8246, 2015, A1, . Location in patent: Page/Page column 17; 18
  • 2
  • [ 140-29-4 ]
  • [ 501-00-8 ]
  • [ 326-62-5 ]
  • [ 459-22-3 ]
  • [ 10036-43-8 ]
Reference: [1] Journal of Fluorine Chemistry, 1990, vol. 49, # 1, p. 115 - 126
  • 3
  • [ 462-06-6 ]
  • [ 107-14-2 ]
  • [ 110-61-2 ]
  • [ 501-00-8 ]
  • [ 326-62-5 ]
  • [ 459-22-3 ]
Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, p. 2728 - 2733
[2] Journal of the Chemical Society, Chemical Communications, 1981, # 16, p. 817 - 818
  • 4
  • [ 140-29-4 ]
  • [ 501-00-8 ]
  • [ 326-62-5 ]
  • [ 459-22-3 ]
  • [ 10036-43-8 ]
Reference: [1] Journal of Fluorine Chemistry, 1990, vol. 49, # 1, p. 115 - 126
  • 5
  • [ 462-06-6 ]
  • [ 107-14-2 ]
  • [ 110-61-2 ]
  • [ 501-00-8 ]
  • [ 326-62-5 ]
  • [ 459-22-3 ]
Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, p. 2728 - 2733
[2] Journal of the Chemical Society, Chemical Communications, 1981, # 16, p. 817 - 818
  • 6
  • [ 18293-53-3 ]
  • [ 460-00-4 ]
  • [ 459-22-3 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 45, p. 15824 - 15832
  • 7
  • [ 352-11-4 ]
  • [ 459-22-3 ]
YieldReaction ConditionsOperation in experiment
60 %Chromat. With palladium diacetate; sodium carbonate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 140℃; for 10 h; Inert atmosphere General procedure: 0.06 mmol PPh3, 0.02 mmol Pd(OAc)2, and 0.4 mL NMP were added into a dried 20 mL tube under a dry nitrogen atmosphere. After the mixture was stirred at room temperature for about 5 min to give a homogeneous solution, 0.3 mmol K4[Fe(CN)6], 1.5 mmol Na2CO3, 1 mmol benzyl chloride, and 0.4 mL NMP were added under a dry nitrogen atmosphere. The reaction tube was sealed with a septum and placed in a constant-temperature oil bath set at 140(+/-5) °C to perform the reaction for 10 h. Once the reaction time was reached, the mixture was cooled to room temperature, then acetophenone was added as an internal standard. GC analysis of the mixture provided the yield of the product (note: in order to decrease the analysis error, the mixture after the reaction was not purified or concentrated). The cyanation product was purified by column chromatography and identified by 1H NMR, 13C NMR or GC-MS data.
85 %Chromat. With copper(l) iodide In toluene at 180℃; for 20 h; Inert atmosphere; Sealed tube General procedure: 0.3 mmol CuI and 0.3 mL toluene were added into a dried 40 mL tube under a dry nitrogen atmosphere. After the mixture was stirred at room temperature for about 1 min, 0.5 mmol K4[Fe(CN)6], 1 mmol benzyl chloride, and 0.7 mL toluene were added under a dry nitrogen atmosphere. The reaction tube was sealed with a septum and placed in a constant-temperature oil bath set at 180(+/-5) °C to perform the reaction for 20 h. Once the reaction time was reached, the mixture was cooled to room temperature, then 1 mL solution of acetophenone (0.8 mmol/mL in dichloromethane) was added as an internal standard into the reaction tube. Subsequently, GC analysis of the mixture provided the yield of the product (note: in order to decrease the analysis error, the mixture after the reaction was not purified or concentrated). The cyanation product was identified by GC-MS data.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 39, p. 5107 - 5109
[2] Tetrahedron Letters, 2012, vol. 53, # 23, p. 2825 - 2827
  • 8
  • [ 1765-93-1 ]
  • [ 107-14-2 ]
  • [ 459-22-3 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 1, p. 50 - 53
[2] Green Chemistry, 2017, vol. 19, # 19, p. 4515 - 4519
  • 9
  • [ 151-50-8 ]
  • [ 459-22-3 ]
Reference: [1] Patent: WO2008/152081, 2008, A2, . Location in patent: Page/Page column 12
  • 10
  • [ 333-20-0 ]
  • [ 210422-66-5 ]
  • [ 459-22-3 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7621 - 7627
  • 11
  • [ 928664-98-6 ]
  • [ 460-00-4 ]
  • [ 459-22-3 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 18, p. 6948 - 6951
  • 12
  • [ 352-33-0 ]
  • [ 1071-36-9 ]
  • [ 459-22-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 19, p. 4470 - 4474
  • 13
  • [ 143-33-9 ]
  • [ 352-11-4 ]
  • [ 459-22-3 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1997, vol. 31, # 3, p. 155 - 157
[2] Roczniki Chemii, 1968, vol. 42, p. 1619 - 1629
[3] Bulletin des Societes Chimiques Belges, 1960, vol. 69, p. 312 - 322
  • 14
  • [ 16647-04-4 ]
  • [ 80482-67-3 ]
  • [ 459-22-3 ]
  • [ 90433-70-8 ]
Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, p. 2746 - 2748
  • 15
  • [ 75-05-8 ]
  • [ 460-00-4 ]
  • [ 459-22-3 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 13, p. 3377 - 3386
  • 16
  • [ 140-29-4 ]
  • [ 501-00-8 ]
  • [ 326-62-5 ]
  • [ 459-22-3 ]
  • [ 10036-43-8 ]
Reference: [1] Journal of Fluorine Chemistry, 1990, vol. 49, # 1, p. 115 - 126
  • 17
  • [ 459-56-3 ]
  • [ 459-22-3 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1997, vol. 31, # 3, p. 155 - 157
[2] Tetrahedron Letters, 2011, vol. 52, # 39, p. 5107 - 5109
  • 18
  • [ 352-32-9 ]
  • [ 459-22-3 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1960, vol. 69, p. 312 - 322
[2] Australian Journal of Chemistry, 1970, vol. 23, p. 1921 - 1937
  • 19
  • [ 143-33-9 ]
  • [ 459-46-1 ]
  • [ 459-22-3 ]
Reference: [1] Australian Journal of Chemistry, 1970, vol. 23, p. 1921 - 1937
  • 20
  • [ 462-06-6 ]
  • [ 107-14-2 ]
  • [ 110-61-2 ]
  • [ 501-00-8 ]
  • [ 326-62-5 ]
  • [ 459-22-3 ]
Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, p. 2728 - 2733
[2] Journal of the Chemical Society, Chemical Communications, 1981, # 16, p. 817 - 818
  • 21
  • [ 459-22-3 ]
  • [ 13101-83-2 ]
Reference: [1] Australian Journal of Chemistry, 1970, vol. 23, p. 1921 - 1937
  • 22
  • [ 459-22-3 ]
  • [ 75-24-1 ]
  • [ 1737-19-5 ]
Reference: [1] Australian Journal of Chemistry, 1970, vol. 23, p. 1921 - 1937
  • 23
  • [ 459-22-3 ]
  • [ 29419-14-5 ]
Reference: [1] Australian Journal of Chemistry, 1970, vol. 23, p. 1921 - 1937
  • 24
  • [ 75-91-2 ]
  • [ 459-22-3 ]
  • [ 58656-98-7 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 104, p. 102023 - 102027
  • 25
  • [ 459-22-3 ]
  • [ 1583-88-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 3, p. 663 - 670
[2] Organic Letters, 2014, vol. 16, # 4, p. 1092 - 1095
[3] Journal of the Chemical Society. Perkin Transactions 1, 2002, vol. 2, # 2, p. 197 - 206
[4] Journal of Organic Chemistry, 1958, vol. 23, p. 1979,1980
  • 26
  • [ 459-22-3 ]
  • [ 157662-77-6 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 4, p. 1131 - 1132
  • 27
  • [ 459-22-3 ]
  • [ 374898-01-8 ]
Reference: [1] ChemCatChem, 2014, vol. 6, # 8, p. 2425 - 2431
[2] ChemCatChem, 2014, vol. 6, # 8, p. 2425 - 2431
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