| Identification | More | [Name]
2-BROMO-4-NITROANILINE | [CAS]
13296-94-1 | [Synonyms]
2-BROMO-4-NITROANILINE
2-BROMO-4-NITRO-PHENYLAMINE
AKOS BBB/074
BUTTPARK 147\16-92
TIMTEC-BB SBB007590
2-bromo-4-nitro-anilin
Aniline, 2-bromo-4-nitro-
2-Bromo-4-nitrobenzenamine
4-Amino-3-bromo-1-nitrobenzene
2-Bromo-4-nitroaniline ,97% | [EINECS(EC#)]
236-318-3 | [Molecular Formula]
C6H5BrN2O2 | [MDL Number]
MFCD00025152 | [Molecular Weight]
217.02 | [MOL File]
13296-94-1.mol |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow solid | [Uses]
2-Bromo-4-nitroaniline is used as a reagent in the synthesis of novel tetrahydrothienopyridopyrimidine derivatives which exhibit antibacterial and antifungal activity against a variety of microorganisms in vitro. Also used as a reagent in synthesis of dialkylimidazole inhibitors of Trypanosoma cruzi sterol 14α-demethylase as anti-Chagas disease agents. | [Synthesis]
Bromine (2.05 mL, 40 mmol) was slowly added dropwise to a solution of 4-nitroaniline (5.0 g, 36 mmol) in acetic acid (150 mL) at room temperature and under argon protection. The reaction mixture was stirred continuously for 2 hours at room temperature. Upon completion of the reaction, the reaction was quenched with dilute aqueous sodium thiosulfate (150 mL) followed by extraction with ethyl acetate (2 x 500 mL). The organic layers were combined and carefully poured into saturated aqueous sodium bicarbonate solution (1 L) and stirred at room temperature for 30 min until the gas release stopped completely. The organic layer was separated, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether/dichloromethane, 3:1) to afford 2-bromo-4-nitroaniline as a yellow solid (6.3 g, 80% yield).1H NMR (400 MHz, CDCl3) δ: 8.39 (1H, d, J = 2.4 Hz), 8.06 (1H, d, J = 2.4 Hz), 6.77 (1H, d, J = 9.2 Hz). | [References]
[1] Synthesis, 2004, # 17, p. 2809 - 2812
[2] Tetrahedron Letters, 2017, vol. 58, # 48, p. 4559 - 4562
[3] Tetrahedron Letters, 2005, vol. 46, # 51, p. 8959 - 8963
[4] Synthetic Communications, 2010, vol. 40, # 21, p. 3226 - 3232
[5] Journal of the American Chemical Society, 1994, vol. 116, # 26, p. 11797 - 11810 |
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