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[ CAS No. 66684-61-5 ] {[proInfo.proName]}

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Chemical Structure| 66684-61-5
Chemical Structure| 66684-61-5
Structure of 66684-61-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 66684-61-5 ]

CAS No. :66684-61-5 MDL No. :MFCD11865203
Formula : C7H5F2NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :DXEGOHULGVHKCT-UHFFFAOYSA-N
M.W :189.12 Pubchem ID :10330129
Synonyms :

Calculated chemistry of [ 66684-61-5 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.67
TPSA : 55.05 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) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.34
Log Po/w (XLOGP3) : 1.92
Log Po/w (WLOGP) : 2.72
Log Po/w (MLOGP) : 2.29
Log Po/w (SILICOS-IT) : 0.55
Consensus Log Po/w : 1.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.43
Solubility : 0.7 mg/ml ; 0.0037 mol/l
Class : Soluble
Log S (Ali) : -2.7
Solubility : 0.378 mg/ml ; 0.002 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.47
Solubility : 0.645 mg/ml ; 0.00341 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 66684-61-5 ]

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 [ 66684-61-5 ]

* 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 [ 66684-61-5 ]
  • Downstream synthetic route of [ 66684-61-5 ]

[ 66684-61-5 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 151414-46-9 ]
  • [ 74-88-4 ]
  • [ 66684-61-5 ]
YieldReaction ConditionsOperation in experiment
87% With potassium carbonate In water; N,N-dimethyl-formamide (Step 2)
Synthesis of 3,5-difluoro-2-nitroanisole
In DMF (50 ml) was dissolved 3,5-difluoro-2-nitrophenol.
Potassium carbonate (10.4 g, 75.5 mmol) and methyl iodide (6.3 ml, 100.6 mmol) were added and the mixture was stirred for 15 hours at room temperature.
Water (300 ml) was added, followed by extraction with ether (500 ml).
The extract was washed with saturated brine (2 * 200 ml), dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, whereby the title compound (8.29 g, 87percent) was obtained as a yellow crystalline powder.
1H-NNR (DMSO-d6) δ: 3.97 (s, 3H), 7.21-7.27 (m, 2H).
Reference: [1] Patent: EP1346982, 2003, A1,
[2] Patent: US2005/176726, 2005, A1, . Location in patent: Page/Page column 30
[3] Patent: US6441012, 2002, B1,
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 18, p. 5876 - 5884,9
  • 2
  • [ 93343-10-3 ]
  • [ 66684-61-5 ]
YieldReaction ConditionsOperation in experiment
72% With nitric acid In dichloromethane at 0℃; for 3 h; 1,5-difluoro-3-methoxy-2-nitrobenzene (A)
To a solution of 3,5-difluoroanisole (30 g, 208 mmol) in 260 mL dichloromethane was added HNO3 (>90percent fuming, 60 mL) dropwise at 0° C.
The resulting solution was stirred at 0° C. for 3 hours, then washed water.
The aqueous phase was extracted with dichloromethane.
The organic phase was washed with brine, dried over magnesium sulfate and condensed on a rotavap.
The residue was recrystallized in hexane and ethyl acetate to provide 28.5 g (72percent yield) of 1,5-difluoro-3-methoxy-2-nitrobenzene as an off-white powder. 1H NMR (400 MHz, DMSO) δ ppm 7.20 (m, 2H), 3.91 (s, 3H).
Reference: [1] Patent: US2009/143367, 2009, A1, . Location in patent: Page/Page column 30
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7621 - 7638
  • 3
  • [ 315-14-0 ]
  • [ 74-88-4 ]
  • [ 66684-61-5 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate In acetone at 50℃; for 2 h; To a solution of 2.45 g (14.0 mmol) of 1,3,5-trifluoro-2-nitrobenzene in acetone are successively added 2.9 g (21.0 mmol) of K2CO3 powder and 3.5 mL (56.0 mmol) of methyl iodide.
The reaction mixture is heated at 50° C. for 2 hours and then filtered and evaporated to dryness.
The residue is taken up in ethyl acetate and washed with water and with saturated aqueous NaCl solution.
The organic phase is dried over Na2SO4, filtered and concentrated under vacuum.
2.52 g of the expected product are recovered in the form of a yellow solid, which is used as obtained in the following step. Yield=95percent.
Reference: [1] Patent: US2012/277220, 2012, A1, . Location in patent: Page/Page column 19
  • 4
  • [ 315-14-0 ]
  • [ 124-41-4 ]
  • [ 66684-62-6 ]
  • [ 66684-61-5 ]
Reference: [1] Journal of Pharmacy and Pharmacology, 1993, vol. 45, # 8, p. 736 - 744
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 9, p. 1362 - 1370
[3] Journal of Pharmacy and Pharmacology, 1993, vol. 45, # 8, p. 736 - 744
[4] Patent: WO2013/171281, 2013, A1, . Location in patent: Page/Page column 155-156
  • 5
  • [ 372-38-3 ]
  • [ 66684-61-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 9, p. 1362 - 1370
[2] Journal of Pharmacy and Pharmacology, 1993, vol. 45, # 8, p. 736 - 744
  • 6
  • [ 67-56-1 ]
  • [ 315-14-0 ]
  • [ 124-41-4 ]
  • [ 66684-61-5 ]
YieldReaction ConditionsOperation in experiment
2.2 g at 0℃; Add 60 mL of methanol to a 100 mL single-mouth bottle.The ice water bath was cooled to 0-10 ° C, and sodium metal (2.6 g, 112.94 mmol) was added in portions, and the mixture was stirred and dissolved to obtain a 2N sodium methoxide solution in methanol.Add in another dry 250mL three-necked bottle1,3,5-trifluoro-2-nitrobenzene (10 g, 56.47 mmol) and methanol (100 mL) were stirred and dissolved.Cool down to 0-5 °C. The sodium methoxide methanol solution prepared above is added dropwise to the system, and the addition is completed.Insulation reaction for 2-3h.Add 2N HCl aqueous solution to adjust the pH to neutral, and pour the reaction solution into 200 mL of purified water.Extract three times with ethyl acetate (100 mL × 3), and combine the organic phases.The mixture was washed twice with saturated brine (100 mL×2), dried over anhydrous sodium sulfate for 30 min, and filtered.The filtrate was concentrated under reduced pressure to give 10 g of crude material.The crude product was stirred with petroleum ether (30 mL) at room temperature and filtered.The filtrate was concentrated under reduced pressure to give 4 g of oily product.The product was eluted with PE/EA = 10/1, and the collected product was concentrated under reduced pressure to give 2.2 g.
Reference: [1] Patent: CN108707139, 2018, A, . Location in patent: Paragraph 0733; 0735; 0736; 0737; 0738
  • 7
  • [ 2713-34-0 ]
  • [ 66684-61-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 18, p. 5876 - 5884,9
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