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[ CAS No. 1201597-22-9 ] {[proInfo.proName]}

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Chemical Structure| 1201597-22-9
Chemical Structure| 1201597-22-9
Structure of 1201597-22-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1201597-22-9 ]

CAS No. :1201597-22-9 MDL No. :MFCD11847293
Formula : C8H6F2O Boiling Point : -
Linear Structure Formula :- InChI Key :BQVVPJZIUSQOAU-UHFFFAOYSA-N
M.W : 156.13 Pubchem ID :21063800
Synonyms :

Calculated chemistry of [ 1201597-22-9 ]

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 : 36.71
TPSA : 17.07 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) : -5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 1.95
Log Po/w (WLOGP) : 2.93
Log Po/w (MLOGP) : 2.63
Log Po/w (SILICOS-IT) : 3.27
Consensus Log Po/w : 2.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.37
Solubility : 0.66 mg/ml ; 0.00423 mol/l
Class : Soluble
Log S (Ali) : -1.93
Solubility : 1.82 mg/ml ; 0.0117 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.28
Solubility : 0.0825 mg/ml ; 0.000528 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.17

Safety of [ 1201597-22-9 ]

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 [ 1201597-22-9 ]

* 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 [ 1201597-22-9 ]
  • Downstream synthetic route of [ 1201597-22-9 ]

[ 1201597-22-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 117358-51-7 ]
  • [ 68-12-2 ]
  • [ 1201597-22-9 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With n-butyllithium In diethyl ether; hexane at -50℃; for 1.83333 h;
Stage #2: at -50℃; for 1.83333 h;
To a solution of 1,3-difluoro-S-methylbenzene (10.2g, 80mmol ) in anhydrous ether ( 80 mL ) was added n-BuLi (2.5 M solution in hexane, 48 ml, 120 mmol) over a 20 min period while the internal temperature was maintained at around -5O°C. After stirring at that temperature for 1.5hr, DMF (14.6g, 200mmol) was added over a 20 min period. After stirring at the same temperature for an additional 1.5 h, the reaction mixture was slowly poured into IN aqueous sulfuric acid (30OmL) and extracted with ether three times. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated to give the title compound (11.2g, 90percent). 1H-NMR (500MHz, CDCl3): δ 10.25 (s, 1H), 6.75 (d, 2H, J=9.9 Hz), 2.39 (s, 3H).
90%
Stage #1: With n-butyllithium In diethyl ether; hexane at -50℃; for 1.83333 h;
Stage #2: at -50℃; for 1.83333 h;
Stage #3: With sulfuric acid; water In diethyl ether; hexane
Step B: 2,6-difluoro-4-methylbenzaldehyde To a solution of 1 ,3-difluoro-5-methylbenzene (10.2g, 80mmol ) in anhydrous ether ( 80 mL ) was added n-BuLi (2.5 M solution in hexane, 48 ml, 120 mmol) over a 20 min period while the internal temperature was maintained at around -5O0C. After stirring at that temperature for 1.5hr, DMF (14.6g, 200mmol) was added over a 20 min period. After stirring at <n="36"/>the same temperature for an additional 1.5 h, the reaction mixture was slowly poured into IN aqueous sulfuric acid (30OmL) and extracted with ether three times. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated to give the title compound (11.2g, 90percent). 1H-NMR (500MHz, CDCl3): δ 10.25 (s, 1H), 6.75 (d, 2H5 J=9.9 Hz), 2.39 (s, 3H).
Reference: [1] Patent: WO2010/129208, 2010, A1, . Location in patent: Page/Page column 32
[2] Patent: WO2009/152072, 2009, A1, . Location in patent: Page/Page column 34-35
[3] Journal of the American Chemical Society, 2018, vol. 140, # 9, p. 3371 - 3377
[4] Patent: WO2011/32277, 2011, A1, . Location in patent: Page/Page column 87
  • 2
  • [ 141776-91-2 ]
  • [ 1201597-22-9 ]
Reference: [1] Patent: WO2009/152072, 2009, A1,
  • 3
  • [ 1201597-22-9 ]
  • [ 1201597-23-0 ]
YieldReaction ConditionsOperation in experiment
53%
Stage #1: With sodium hydroxide; silver(l) oxide In water for 1.5 h;
Stage #2: With hydrogenchloride In water
Silver oxide (43.8 g, 0.189mol) was placed in a flask along with water (20OmL) and sodium hydroxide (33.7g, 0.842mol). To it was added 2,6-difluoro-4-methylbenzaldehyde (29.23 g, 0.187mol) in small portions over a 30min period. After a vigorous exothermic reaction, the color of the reaction mixture changed from black to gray. The resulting thick suspension was stirred for 1 hr and then filtered through a Buchner funnel. The filtrate was acidified to pH 2 with concentrated HCl to give a suspension. The precipitate was collected by suction filtration, dissolved in ether, dried over anhydrous Na2SO4, filtered and concentrated to give white solid (17.0 g, 53percent). 1H-NMR (500MHz, d6-DMSO): 613.7 ( br.s, 1H ), 7.02 ( d, 2H, J=9.3 Hz), 2.32 ( s, 3H ).
53%
Stage #1: With sodium hydroxide In hexane; water for 1.5 h;
Stage #2: With hydrogenchloride In hexane; water
Step C: 2,6-difluoro-4-methylbenzoic acid Silver oxide (43.8 g, 0.189mol) was placed in a flask along with water (20OmL) and sodium hydroxide (33.7g, 0.842mol). To it was added 2,6-difluoro-4-methylbenzaldehyde (29.23 g, 0.187mol) in small portions over a 30min period. After a vigorous exothermic reaction, the color of the reaction mixture changed from black to gray. Resulting thick suspension was stirred for 1 hr, filtered through a Buchner funnel. The filtrate was acidified to pH 2 with concentrated HCl to give a suspension. The precipitate was collected by suction filtration, dissolved in ether and dried over anhydrous Na2SO4, filtered and concentrated to give white solid (17.0 g, 53percent). 1H-NMR (500MHz, d6-DMSO): 613.7 ( br.s, 1H ), 7.02 ( d, 2H, J=9.3 Hz), 2.32 ( s, 3H ).
Reference: [1] Patent: WO2010/129208, 2010, A1, . Location in patent: Page/Page column 32-33
[2] Patent: WO2009/152072, 2009, A1, . Location in patent: Page/Page column 35
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