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[ CAS No. 28987-44-2 ]

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Chemical Structure| 28987-44-2
Chemical Structure| 28987-44-2
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CAS No. :28987-44-2 MDL No. :MFCD04115630
Formula : C8H8FNO3 Boiling Point : 261.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :185.15 g/mol Pubchem ID :-
Synonyms :

Safety of [ 28987-44-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 28987-44-2 ]

  • Downstream synthetic route of [ 28987-44-2 ]

[ 28987-44-2 ] Synthesis Path-Downstream   1~16

YieldReaction ConditionsOperation in experiment
Example 40-41 Compound 40 (m.p.=133-135 C.) and compound 41(m.p.=151-153 C.) were obtain from 4-fluoro-2-ethoxy-nitrobenzene by proceeding in a similar manner described in Experimental 39 step (a).
  • 4
  • [ 75-89-8 ]
  • [ 446-35-5 ]
  • [ 28987-44-2 ]
  • [ 186386-91-4 ]
YieldReaction ConditionsOperation in experiment
With tert-butoxide; In tetrahydrofuran; at 0℃; for 0.5h; To a solution of trifluoroethanol in 4 mL dry THF, was added tert-butoxide (378 mg, 3.37 mmol) at 0 C. The resulting mixture was added dropwise to the solution of 2, 4-difluoro-1-nitro-benzene (536 mg, 3.37 mmol) in 5 mL dry THF at 0C. The mixture was stirred at 0C for 30 minutes, then diluted with ethyl acetate and washed with brine. The organic layers were combined and concentrated in vacuo to give 4-fluoro-l-nitro-2- (2, 2,2- trifluoro-ethoxy)-benzene.
  • 5
  • [ 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+).
  • 6
  • [ 28987-44-2 ]
  • [ 178993-28-7 ]
YieldReaction ConditionsOperation in experiment
92% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; After the 5-fluoro-2-nitro-ethyl ether (6.8g) was dissolved in 150ml of methanol was added 10% Pd / C (680mg), purged with hydrogen, hydrogenated at room temperature with stirring. After completion of the reaction by TLC, filtered and the filtrate reduced the solvent was evaporated press 4-fluoro-2-ethoxy-aniline (5.2g, 92% yield).
92% With palladium on activated charcoal; hydrogen; In methanol; at 20℃; 5-fluoro-2-nitrophenylethyl ether (6.8 g) was dissolved in 150 ml of methanol,After addition of palladium on carbon (680 mg)Hydrogen replacement,Room temperature stirring hydrogenation,After TLC detection reaction was completed,filter,The filtrate was evaporated under reduced pressure to give 4-fluoro-2-ethoxyaniline (5.2 g, yield 92%).
(2) Synthesis of 2-Ethoxy-4-fluoroaniline By similar reaction and treatment to that in Example 40(2) using 2-ethoxy-4-fluoronitrobenzene instead of 4-fluoro-2-methoxynitrobenzene, the title compound was obtained as a black oil. 1H-NMR(CDCl3)δ: 1.44(3H, t, J=7.3 Hz), 3.50(2H, br.s), 4.00(2H, q, J=7.3 Hz), 6.27-6.64(3H, m). IR(KBr): 3548, 3369, 2981, 1618, 1512 cm-1; MS(EI): 155(M+).
56 g With palladium on activated charcoal; hydrogen; In methanol; at 20℃; for 4h; 5-fluoro-2-nitrophenylethyl ether (68 g) was dissolved in 1 L of methanol, After the addition of palladium on carbon (5 g), the hydrogen was replaced twice and stirred at room temperature for about 4 hours. After the reaction was complete, the reaction was filtered and the filtrate was evaporated under reduced pressure to give 4-fluoro-2-ethoxyaniline 56g).
With palladium 10% on activated carbon; hydrogen; In methanol; for 3h; Intermediate 3: 2-Ethoxy-4-fluorobenzenamine To a 250 mL round-bottomed flask were added <strong>[28987-44-2]2-ethoxy-4-fluoro-1-nitrobenzene</strong> (3.70 g, 20.0 mmol) and 10% Pd/C (370 mg) in MeOH (80.0 mL). The mixture was stirred at rt for 3 h under a H2 atmosphere. The mixture was filtered and the filtrate was concentrated to dryness to give the title product (2.8 g, crude, 90%) as a dark oil. MS (ESI): mass calcd. for C8H10FNO 155.07, m/z found 156.2 [M+H]+.
3.8 g With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; 10% 42 Pd/C (400 mg) was added into the solution of 345 <strong>[28987-44-2]2-ethoxy-4-fluoro-1-nitrobenzene</strong> (4.8 g, 26.0 mmol) in 43 methanol (40 mL), and reacted under hydrogen gas (balloon) at room temperature overnight, filtered on Celite, the filtrate was concentrated under reduced pressure, and the filtrate was separated on column chromatography (eluant:petroleum ether/ethyl acetate (v/v)=50:1), and afforded product 3.8 g of a pale yellow oil, LC-MS(APCI): m/z=156.1 (M+1). 1H NMR (400 MHz, CDCl3) δ 6.63 (dd, J=8.5, 5.8 Hz, 1H), 6.56 (dd, J=10.4, 2.7 Hz, 1H), 6.50 (td, J=8.5, 2.7 Hz, 1H), 4.04 (q, J=7.0 Hz, 2H), 3.42 (br, 2H), 1.45 (t, J=7.0 Hz, 3H).

  • 7
  • [ 446-35-5 ]
  • [ 28987-44-2 ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate; In ethanol; EXAMPLE 26A 2-Ethoxy-4-fluoronitrobenzene To a solution of anhydrous sodium ethoxide (0.55 mole) [prepared by dissolving sodium metal (12.6 g, 0.55 mole) in anhydrous ethanol (300 ml)] at 0 C. is added 2,4-difluoronitrobenzene (79.5 g, 0.50 mole) dropwise over an 8 hour period. Upon completion of addition the reaction mixture is allowed to warm to room temperature and stirred overnight. The solid is removed by filtration, and triturated with toluene and water. The toluene extract is combined with the original filtrate, dried with anhydrous sodium sulfate and the solvent is removed under vacuum to afford 218 g of a yellow oil which was distilled at 0.3 mm, b.p. 95-98 C. to afford substantially pure 2-ethoxy-4-fluoronitrobenzene. STR20
  • 8
  • [ 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.

  • 9
  • [ 110-85-0 ]
  • [ 28987-44-2 ]
  • [ 1089280-28-3 ]
YieldReaction ConditionsOperation in experiment
88% In 1,4-dioxane; at 120℃; for 72h; To 2-(ethyloxy)-4-fluoro-1-nitrobenzene (Example 116, step A) (3.0 g, 16.2 mmol) in 60 mL of dioxane was added, piperazine (4.19 g, 48.61 mmol). The mixture was heated to 120 C. 72 h. The mixture was purified by flash chromatography to give the title compound of step A (3.6 g, 14.33 mmol, 88%). 1H NMR (400 MHz, CDCl3) δ ppm 7.95 (d, J=9.34 Hz, 1H), 6.40 (dd, J=9.34, 2.56 Hz, 1H), 6.30 (d, J=2.56 Hz, 1H), 4.13 (q, J=6.96 Hz, 2H), 3.30-3.33 (m, 4H), 2.95-3.02 (m, 4H), 1.48 (t, J=6.96 Hz, 3H).
  • 10
  • [ 50533-97-6 ]
  • [ 28987-44-2 ]
  • [ 1124330-03-5 ]
YieldReaction ConditionsOperation in experiment
100% With N-ethyl-N,N-diisopropylamine; In ISOPROPYLAMIDE; at 100℃; for 4h; 4-(Dimethylamino)piperidine (2.89 g) was added to a stirred solution of 2-ethoxy-4-fluoro- 1 -nitrobenzene (3.79 g) and DIPEA (7.1 mL) in DMA (17.5 mL). The mixture was then heated to 1000C for 4h. The mixture was then concentrated in vacuo and purified by SCX, eluting with 7M NH3/ MeOH to afford the title compound (6.10 g, 102 %) as a yellow solid; 1H NMR: 1.39 (5H, m), 1.82 (2H, d), 2.19 (6H, s), 2.36 (IH, m), 2.96 (2H, t), 4.00 (2H, d), 4.19 (2H, q), 6.50 (IH, dd), 6.58 (IH, d), 7.86 (IH, d); m/z: MH+ 294.
  • 11
  • [ 108-01-0 ]
  • [ 28987-44-2 ]
  • [ 1124330-06-8 ]
YieldReaction ConditionsOperation in experiment
55% With potassium hydroxide;tetrabutylammomium bromide; In water; toluene; at 80℃; for 16h; 7V,7V-Dimethylethanolamine (5.02 mL) was added a mixture of 2-ethoxy-4-fluoro-l- nitrobenzene (4.63 g) and tetra-n-butylammonium bromide (1.61 g) in toluene (20 mL) and 25% w/v aq. KOH (20 mL). The mixture was heated to 800C for 16h and was then poured onto ice water (50 mL). The resulting mixture was extracted with EtOAc (3 x 100 mL). The combined organic portions were washed with water (2 x 50 mL) and brine (2 x 50 mL), dried (MgSO4) and concentrated in vacuo. Purification by FCC using 5-10% (2M NH3 /MeOH) in DCM afforded the title compound (3.50 g, 55%) as a yellow gum; 1H NMR: 1.35 (3H, t), 2.23 (6H, s), 2.65 (2H, t), 4.20 (4H, m), 6.66 (IH, dd), 6.79 (IH, d), 7.92 (IH, ); m/z: MH+ 255.
  • 12
  • [ 4318-37-0 ]
  • [ 28987-44-2 ]
  • [ 1124330-01-3 ]
YieldReaction ConditionsOperation in experiment
95% With N-ethyl-N,N-diisopropylamine; In ISOPROPYLAMIDE; at 100℃; for 4h; <strong>[4318-37-0]1-Methylhomopiperazine</strong> (2.82 mL) was added to a stirred solution of 2-ethoxy-4-fiuoro-l- nitrobenzene (3.5 g) and DIPEA (6.54 mL) in DMA (17.5 mL). The mixture was heated at 1000C for 4h then diluted with water (75 mL) and extracted with DCM (3 x 150 mL). The combined organic portions were washed with brine (3 x 75 mL), dried (Na2SO4) and concentrated in vacuo to afford the title compound (5.0 g, 95%) as a gum; 1H NMR: 1.37 (3H, t), 1.94-1.87 (2H, m), 1.96 (3H, s), 2.67 (2H, t), 3.57 (2H, t), 3.66-3.63 (2H, m), 4.18 (2H, q), 6.27 (IH, d), 6.42 (IH, dd), 7.87 (IH, d); m/z: MH+ 280.
  • 13
  • [ 109-01-3 ]
  • [ 28987-44-2 ]
  • 1-(3-ethoxy-4-nitro-phenyl)-4-methyl-piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% at 20℃; for 18h; (b)1-(3-ethoxy-4-nitro-phenyl)-4-methyl-piperazineN-Methylpiperazine (603 pL, 5.44 mmol) was added to 2-ethoxy-4-fluoro-1-nitro-benzene (500 mg, 2.7 mmol) and the resulting mixture was stirred at room temperature for 18 hours. Water was added to the reaction mixture and subsequently extracted with ethyl acetate.The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacua. The crude product was purified by column chromatography on silica (DCM/MeOH = 10/0 to 9/1 vlv%) to yield the title compound (646 mg, 90%).
  • 14
  • [ 28987-44-2 ]
  • [ 760968-77-2 ]
  • [ 951667-63-3 ]
YieldReaction ConditionsOperation in experiment
50% 5-Hydroxy-2-(toluene-4-sulfonylamino)-benzoic acid methyl ester (200 mg, 0.622 mmol) was dissolved in dry DMF (5 ml) under Nitrogen. Added K2CO3 (215 mg, 1.56 mmol) and 2-Ethoxy-4-fluoro-1-nitro-benzene (121 mg, 0.653 mmol). Heated to 80 C. for 3 hours. Cooled to room temperature. Added EtOAc, washed with 0.5 M KHSO4 (2×25 ml), aq. sat. NH4Cl (25 ml), 0.5 M NaOH (2×25 ml) and aq. sat. NaCl (25 ml). Dried over Na2SO4, filtered off and concentrated in vacuo. Stripped with CH2Cl2. Stirred up in EtOH. Gave crystal formation. Filtered off and washed with EtOH, dried on filter and on vacuo line. Gave an off white solid 150 mg (y:50%).LC: >95%MS: [M+H]+=487
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  • [ 110-91-8 ]
  • [ 28987-44-2 ]
  • [ 415686-74-7 ]
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  • [ 28987-44-2 ]
  • [ 1246529-73-6 ]
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