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[ CAS No. 446-36-6 ] {[proInfo.proName]}

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Chemical Structure| 446-36-6
Chemical Structure| 446-36-6
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Product Details of [ 446-36-6 ]

CAS No. :446-36-6 MDL No. :MFCD00007107
Formula : C6H4FNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :QQURWFRNETXFTN-UHFFFAOYSA-N
M.W : 157.10 Pubchem ID :9937
Synonyms :

Calculated chemistry of [ 446-36-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.24
TPSA : 66.05 ?2

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) : -5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.86
Log Po/w (XLOGP3) : 1.91
Log Po/w (WLOGP) : 1.86
Log Po/w (MLOGP) : 0.7
Log Po/w (SILICOS-IT) : -0.35
Consensus Log Po/w : 1.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.35
Solubility : 0.694 mg/ml ; 0.00442 mol/l
Class : Soluble
Log S (Ali) : -2.92
Solubility : 0.189 mg/ml ; 0.0012 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.47
Solubility : 5.34 mg/ml ; 0.034 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 446-36-6 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501 UN#:3077
Hazard Statements:H302-H315-H317-H318-H410 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 446-36-6 ]

* 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.

  • Downstream synthetic route of [ 446-36-6 ]

[ 446-36-6 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 446-36-6 ]
  • [ 56-81-5 ]
  • [ 135838-04-9 ]
  • 2
  • [ 446-36-6 ]
  • [ 4045-25-4 ]
  • [ 859217-96-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In DMF (N,N-dimethyl-formamide); at 80℃; for 3.5h; A mixture of <strong>[4045-25-4]4-methoxypiperidine hydrochloride</strong> (9.10 g, 60.01 mmol) prepared in Example (7a), 5-fluoro-2-nitrophenol (6.91 g, 43.98 mmol) and dimethylformamide (12 mL) was stirred under a nitrogen atmosphere. Triethylamine (15.24 mL, 109.95 mmol) was added to the reaction mixture and the mixture was stirred at an external temperature of 80 C. for 3 hours and 30 minutes. After the reaction, saturated aqueous ammonium chloride and a mixed solvent of ethyl acetate-diethyl ether was added to the reaction mixture. The organic layer was separated off, and the aqueous layer was extracted with diethyl ether. The obtained organic layers were combined and dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 37.36 g of the title compound as orange crystals. 1H-NMR (400 MHz, CDCl3) delta: 1.60-1.68 (m, 2H), 1.83-1.90 (m, 2H), 3.26 (ddd, J=13.2, 8.0, 3.6 Hz, 2H), 3.32 (s, 3H), 3.42-3.47(m, 1H), 3.62 (ddd, J=13.2, 7.6, 3.6 Hz, 2H), 6.24 (d, J=2.8 Hz, 1H), 6.36 (dd, J=10.0, 2.8 Hz, 1H), 7.87 (d, J=10.0 Hz, 1H). The 1H of OH could not be identified.
  • 3
  • [ 7583-53-1 ]
  • [ 446-36-6 ]
  • [ 457099-08-0 ]
YieldReaction ConditionsOperation in experiment
1-[4-Fluoro-2-(1-methyl-piperidin-3-ylmethoxy)-phenyl]-3-(5-methyl-pyrazin-2-yl)-urea Prepared according to the methods for compound 303, using 2-nitro-5-fluorophenol and 1-methyl-3-hydroxymethyl piperidine. 1H NMR (400 MHz, CDCl3) delta8.50 (br s, 1H), 8.19 (m, 2H), 6.65 (m, 2H), 3.85 (m, 2H), 3.60 (s, 3H), 2.80-3.20 (m, 2H), 2.54 (s, 3H), 2.39 (s, 3H), 1.60-2.10 (m 5H). LRMS (ESI, Positive) m/e 373.95 (M+1).
  • 4
  • [ 446-36-6 ]
  • [ 1972-28-7 ]
  • [ 28987-44-2 ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; In tetrahydrofuran; ethanol; di-isopropyl ether; ethyl acetate; (1) Synthesis of 2-Ethoxy-4-fluoronitrobenzene To a solution of ethanol (4.2 ml) in tetrahydrofuran (65 ml) was added a solution of triphenylphosphine (13 g) and 5-fluoro-2-nitrophenol (10 g) in tetrahydrofuran (65 ml). To this solution was added diethyl azodicarboxylate (10 ml) under ice-cooling and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated under reduced pressure and diisopropyl ether was added. The precipitated crystals were collected by filtration and concentrated under reduced pressure. The concentrate was subjected to silica gel column chromatography (developing solvent; hexane:ethyl acetate=4:1) to give a yellow oil. To this oil was added ethyl acetate, washed with an aqueous sodium hydroxide solution, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (9.6 g) as a yellow oil. 1H-NMR(CDCl3)δ: 1.50(3H, t, J=7.3 Hz), 4.17(2H, q, J=7.3 Hz), 6.67-6.79(2H, m), 7.92(1H, dt, J=3.3, 2.6 Hz). MS(EI): 185(M+).
  • 5
  • [ 446-36-6 ]
  • [ 75-03-6 ]
  • [ 28987-44-2 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate; In acetone; for 15h;Reflux; Intermediate 2: 2-Ethoxy-4-fluoro-1-nitrobenzene To a 100 mL round-bottomed flask were added a mixture of 5-fluoro-2-nitrophenol (3.14 g, 20.0 mmol), iodoethane (3.43 g, 22.0 mmol), K2CO3 (5.52 g, 40.0 mmol), and acetone (30.0 mL). The mixture was heated at reflux for 15 h, and then concentrated under vacuum to dryness. Water (30 mL) was added to the residue and the resulting mixture was extracted with EtOAc (3*20 mL). The combined organic phases were washed with saturated NaCl(aq) (30 mL), dried over anhydrous Na2SO4, and concentrated to dryness to give the title compound (3.7 g, 100%) as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.92 (dd, J=9.0, 6.0 Hz, 1H), 6.80-6.65 (m, 2H), 4.17 (q, J=7.0 Hz, 2H), 1.51 (t, J=7.0 Hz, 3H).
99% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 24h;sealed tube; To 5-fluoro-2-nitrophenol (8.3 g, 52.83 mmol) in 50 mL of DMF was added K2CO3 (14.6 g, 105.7 mmol), and ethyl iodide (8.53 mL, 105.7 mmol). The mixture was stirred at 60 C. for 24 h in a sealed tube. The mixture was poured into 500 mL of H2O and extracted with diethyl ether, dried (Na2SO4), filtered, and rotovaped down to give the title compound of step A (9.69 g, 52.33 mmol, 99%). 1H NMR (400 MHz, CDCl3) δ ppm 7.88-7.94 (m, 1H), 6.71-6.77 (m, 1H), 6.66-6.71 (m, 1H), 4.11-4.19 (m, 2H), 1.45-1.51 (m, 3H).
85% With potassium carbonate; In butanone; at 80℃; for 18h;Inert atmosphere; Dissolved the commercially available 5-fluoro-2-nitrophenol (250 mg, 1.59 mmol) in 2-butanone (10 ml) under Nitrogen. Added K2CO3 (659 mg, 4.77 mmol) and iodo-ethane (260 mg, 1.67 mmol). Stirred at 80 C. for 18 hours. Cooled, filtered off and washed with 2-butanone. The filtrate was concentrated in vacuo. Redissolved in EtOAc and washed with 0.5N NaOH (2×25 ml) and aq. sat. NaCl (25 ml). Dried over Na2SO4, filtered off and concentrated in vacuo. Gave 251 mg (85%) yellow liquid.GC: >95%MS: [M]+=185
83.1% With potassium carbonate; In N,N-dimethyl-formamide; at 37℃; 5-fluoro-2-nitrophenol (5.0 g, 31.8 mmol), 56 potassium carbonate (13.17 g, 95.4 mmol) were suspended in 150 mL 40 DMF, 346 ethyl iodide (5.00 mL, 63.6 mmol) was added dropwise, and the reaction was heated to 37 C. with stirring. After TLC detected the reaction was complete, the system was poured in 252 ice-water, extracted with ethyl acetate (200 mL×3), the organic layer was combined, washed with brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the filtrate was separated on column chromatography (eluant:petroleum ether/ethyl acetate (v/v)=20:1), to afford 4.8 g of a yellow oil. Yield was 83.1%.
With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; 5-fluoro-2-nitrophenol (300 mg), ethyliodide (0.50 mL) and potassium carbonate (500 mg) were dissolved in dimethylformamide (DMF, 3 mL), and reacted at 50 C. overnight. The dimethylformamide of the reaction mixture was concentrated under reduced pressure, added with water and the organic layer was extracted with ethyl acetate. The organic layer was washed with brine, and the water was removed with sodium sulfate, and the solvent was removed under reduced pressure. The thus obtained compound was used in the subsequent reaction without further purification.
With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; Step 1: Preparation of 4-fluoro-2-ethoxy-1-nitrobenzene 5-fluoro-2-nitrophenol (300 mg), ethyliodide (0.50 mL) and potassium carbonate (500 mg) were dissolved in dimethylformamide (DMF, 3 mL), and reacted at 50C overnight. The dimethylformamide of the reaction mixture was concentrated under reduced pressure, added with water and the organic layer was extracted with ethyl acetate. The organic layer was washed with brine, and the water was removed with sodium sulfate, and the solvent was removed under reduced pressure. The thus obtained compound was used in the subsequent reaction without further purification.

  • 7
  • [ 446-36-6 ]
  • [ 19362-77-7 ]
  • [ 1467066-71-2 ]
  • 8
  • [ 74-96-4 ]
  • [ 446-36-6 ]
  • [ 28987-44-2 ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate; In N,N-dimethyl-formamide; at 37℃; 5-fluoro-2-nitrophenol (120 g, 1 eq), potassium carbonate (316 g, 3 eq) was suspended in 2 L DMF, and bromoethane (166 g, 2 eq) The temperature was raised to 37 C, After the TLC test reaction was completed, the system was poured into ice water and the product precipitated and washed with water to give 5-fluoro-2-nitrophenylethyl ether (138.6 g, yield 98%).
97% With potassium carbonate; In N,N-dimethyl-formamide; at 37℃; The 5-fluoro-2-nitrophenol (6g, 1eq), potassium carbonate (15.8g, 3eq) was suspended in 150mlN, N, N-Dimethylformamide, was added dropwise bromoethane (8.3g, 2eq), the reaction temperature was raised to 37 [deg.] C with stirring, TLC detection reactionAfter completion, the system was poured into ice water, the precipitated product was filtered washed with diethyl ether to give 5-fluoro-2-nitrobenzene (6.8g, yield97%).
97% With potassium carbonate; In N,N-dimethyl-formamide; at 35 - 40℃; 5-fluoro-2-nitrophenol (6 g, 1 eq),Potassium carbonate (15.8 g, 3 eq)Was added to 150 ml of N, N-dimethylformamide,Bromoethane (8.3 g, 2 eq) was added dropwise with stirring,Raising the temperature to 35-40 C stirring reaction,After TLC detection reaction was completed,The reaction solution was poured into ice water,Product precipitation, filtration, washing,5-fluoro-2-nitrophenylethyl ether (6.8 g, yield 97%).
  • 9
  • [ 446-36-6 ]
  • [ 56346-41-9 ]
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