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[ CAS No. 231291-22-8 ] {[proInfo.proName]}

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Chemical Structure| 231291-22-8
Chemical Structure| 231291-22-8
Structure of 231291-22-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 231291-22-8 ]

CAS No. :231291-22-8 MDL No. :MFCD00792430
Formula : C7H4F3NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JNYLMODTPLSLIF-UHFFFAOYSA-N
M.W : 191.11 Pubchem ID :2777551
Synonyms :

Calculated chemistry of [ 231291-22-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.2
TPSA : 50.19 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) : -6.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.16
Log Po/w (XLOGP3) : 1.3
Log Po/w (WLOGP) : 2.95
Log Po/w (MLOGP) : -0.02
Log Po/w (SILICOS-IT) : 1.77
Consensus Log Po/w : 1.43

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.05
Solubility : 1.69 mg/ml ; 0.00884 mol/l
Class : Soluble
Log S (Ali) : -1.95
Solubility : 2.12 mg/ml ; 0.0111 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.985 mg/ml ; 0.00515 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 231291-22-8 ]

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

Application In Synthesis of [ 231291-22-8 ]

* 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 [ 231291-22-8 ]
  • Downstream synthetic route of [ 231291-22-8 ]

[ 231291-22-8 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 124-38-9 ]
  • [ 368-48-9 ]
  • [ 131747-42-7 ]
  • [ 131747-41-6 ]
  • [ 131747-43-8 ]
  • [ 231291-22-8 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1569 - 1575
  • 2
  • [ 124-38-9 ]
  • [ 368-48-9 ]
  • [ 131747-42-7 ]
  • [ 131747-41-6 ]
  • [ 131747-43-8 ]
  • [ 231291-22-8 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1569 - 1575
  • 3
  • [ 124-38-9 ]
  • [ 368-48-9 ]
  • [ 131747-42-7 ]
  • [ 131747-41-6 ]
  • [ 131747-43-8 ]
  • [ 231291-22-8 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1569 - 1575
  • 4
  • [ 216431-85-5 ]
  • [ 231291-22-8 ]
YieldReaction ConditionsOperation in experiment
97.3% Reflux In a 10L three-necked flask was charged water 1420g, sulfuric acid 2440g, glacial acetic acid 150mL slowly added 6- (trifluoromethyl) nicotinonitrile 870g (5mol).Reflux overnight reaction.Cool, add ice and cool with ice-brine to precipitate a white solid.The filtrate was extracted with ethyl acetate. The organic phases were combined, washed twice with water and the organic phase was dried to dryness and acid-washed to give 930 g of 6-(trifluoromethyl)-3-picolinic acid as a beige solid. The yield was 97.3percent.
97.3% With sulfuric acid; acetic acid In waterReflux In a 10 L three-necked flask, 1420 g of water, 2440 g of sulfuric acid and 150 mL of glacial acetic acid were added, and 870 g (5 mol) of 6- (trifluoromethyl) nicotinonitrile was added slowly.Reflux overnight reaction. Cooling, adding ice cubes, and cooling with ice brine, precipitating a white solid was filtered, the filtrate was extracted with ethyl acetate, the organic phases were combined, washed twice with water, the organic phase was dried and swirled,The residue was acid washed to give 930 g of 5- (trifluoromethyl) picolinic acid as an off-white solid in a yield of 97.3percent.
Reference: [1] Patent: CN107298677, 2017, A, . Location in patent: Paragraph 0036-0038
[2] Patent: CN107337638, 2017, A, . Location in patent: Paragraph 0031; 0032; 0033
[3] Patent: EP1122242, 2001, A1,
[4] Patent: US6673799, 2004, B1, . Location in patent: Page column 16
  • 5
  • [ 64-19-7 ]
  • [ 216431-85-5 ]
  • [ 231291-22-8 ]
YieldReaction ConditionsOperation in experiment
97.3% With sulfuric acid In waterReflux In a 10 L three-necked flask, 1420 g of water, 2440 g of sulfuric acid, and 150 mL of glacial acetic acid were added, and 870 g (5 mol) of 6-(trifluoromethyl)nicotinonitrile was slowly added thereto.The reaction was refluxed overnight.The temperature was lowered, ice was added, and cooled with iced brine to precipitate a white solid.After filtration, the filtrate was extracted with ethyl acetate. The organic phases were combined and washed twice with water. The organic phase was dried by rotary evaporation and the acid eluted to give 930 g of 6-(trifluoromethyl)picolinic acid as an off-white solid. The yield was 97.3percent.
Reference: [1] Patent: CN107382989, 2017, A, . Location in patent: Paragraph 0021; 0036-0038
  • 6
  • [ 124-38-9 ]
  • [ 436799-32-5 ]
  • [ 231291-22-8 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
  • 7
  • [ 624-28-2 ]
  • [ 231291-22-8 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
[2] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
[3] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
  • 8
  • [ 30766-11-1 ]
  • [ 231291-22-8 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
  • 9
  • [ 223463-13-6 ]
  • [ 231291-22-8 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
  • 10
  • [ 124-38-9 ]
  • [ 368-48-9 ]
  • [ 131747-42-7 ]
  • [ 131747-41-6 ]
  • [ 131747-43-8 ]
  • [ 231291-22-8 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1569 - 1575
  • 11
  • [ 231291-22-8 ]
  • [ 386704-12-7 ]
Reference: [1] Patent: US2011/178134, 2011, A1,
[2] Patent: WO2008/148853, 2008, A1,
  • 12
  • [ 231291-22-8 ]
  • [ 386715-33-9 ]
Reference: [1] Patent: US2013/131036, 2013, A1,
[2] Patent: WO2013/62966, 2013, A2,
[3] Patent: US2014/107340, 2014, A1,
[4] Patent: JP2017/178911, 2017, A,
  • 13
  • [ 231291-22-8 ]
  • [ 358780-14-0 ]
Reference: [1] Patent: US2012/302608, 2012, A1,
[2] Patent: WO2015/191630, 2015, A1,
  • 14
  • [ 64-17-5 ]
  • [ 231291-22-8 ]
  • [ 597532-36-0 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 14, p. 3434 - 3437
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