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Chemical Structure| 178993-28-7 Chemical Structure| 178993-28-7

Structure of 178993-28-7

Chemical Structure| 178993-28-7

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Product Details of [ 178993-28-7 ]

CAS No. :178993-28-7
Formula : C8H10FNO
M.W : 155.17
SMILES Code : NC1=CC=C(F)C=C1OCC
MDL No. :MFCD07801192

Safety of [ 178993-28-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Application In Synthesis of [ 178993-28-7 ]

* 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 [ 178993-28-7 ]

[ 178993-28-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 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).

 

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