2-Bromo-5-fluoro-4-nitrobenzenamine
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2-Bromo-5-fluoro-4-nitrobenzenamine
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CAS No:
952664-69-6
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Formula:
C6H4BrFN2O2
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Chemical Name:
2-Bromo-5-fluoro-4-nitrobenzenamine
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Synonyms:
Benzenamine,2-bromo-5-fluoro-4-nitro-;2-Bromo-5-fluoro-4-nitrobenzenamine;2-Bromo-5-fluoro-4-nitroaniline
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CAS No:
2-Bromo-5-fluoro-4-nitrobenzenamine Use and Manufacturing
To a mixture of 3-fluoro-4-nitroaniline (6.5 g, 42.2 mmol) in AcOH (80 mL) and chloroform (25 mL) was added dropwise Br2-Bromo-5-fluoro-4-nitroanilineTo a mixture of 3-fluoro-4-nitroaniline (6.5 g, 42.2 mmol) in AcOH (80 mL) and chloroform (25 mL) was added dropwise BrTo a solution of 3-fluoro-4-nitroaniline (56 g, 0.36 mol) in acetic acid (500 mL) was added drop-wise bromine (17.7 mL, 0.36 mol) over 1 hour. The reaction mixture was stirred for 1 hour at 0-5 °C in an ice bath. The reaction mixture was basified with saturated NaStep 1214 15[00168] methyl 2.2-difluorobenzo[d1[1.31dioxole-5-carboxylate: To a solution of 3- fluoro-4-nitroaniline (6.5 g, 41.64 mmol, 1.00 equiv) in chloroform (25 mL) and AcOH (80 mL) was added Bn (6.58 g, 41.17 mmol, 1.00 equiv.) dropwise with stirring at 0 °C in 20 min. The resulting solution was stirred for 2 h at room temperature. The reaction was then quenched by the addition of 150 mL of water/ice. The pH value of the solution was adjusted to 9 with sodium hydroxide (10 percent). The resulting solution was extracted with 3 x 50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1 x 50 mL of water and 2 x 50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was re-crystallized from PE/EA (10: 1) to afford 6 g (61percent) of 2-bromo-5-fluoro-4-nitroaniline as a yellow solid.Synthesis of 2-bromo-5-fluoro-4-nitroaniline Synthesis of 2-bromo-5-fluoro-4-nitroaniline A flask was charged with 3-fluoro-4-nitroaniline (1.0 equiv) followed by ethyl acetate (10 vol) and stirred to dissolve all solids. N-Bromosuccinimide (1.0 equiv) was added as a portion-wise as to maintain internal temperature of 22 °C. At the end of the reaction, the reaction mixture was concentrated in vacuo on a rotavap. The residue was slurried in distilled water (5 vol) to dissolve and remove succinimide. (The succinimide can also be removed by water workup procedure.) The water was decanted and the solid was slurried in 2-propanol (5 vol) overnight. The resulting slurry was filtered and the wetcake was washed with 2-propanol, dried in vacuum oven at 50 °C overnight with NExample 172A 2-({1-[(benzyloxy)methyl]cyclobutyl}ethynyl)-5-fluoro-4-nitroaniline A mixture of Step 3[00193] N-[3-(benzyloxy)-2-hvdroxy(3.3-2H2)propyl1-
Computed Properties
Molecular Weight:235.01
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:233.94402
Monoisotopic Mass:233.94402
Topological Polar Surface Area:71.8
Heavy Atom Count:12
Complexity:187
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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2-Bromo-5-fluoro-4-nitrobenzenamine
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