2-Bromo-6-nitrobenzenamine

Pale yellow powder

To a solution of 2-nitroaniline (34.5 g, 0.25 mol) in aceticacid (400 ml), N-bromosuccinimide (44.5 g, 0.25 mol) wasadded portionwise over a period of 30 min at 308–318 K(Fig. 1). The mixture was stirred for 3 h at 318 K, warmed to363 K and stirred for 2 h. After cooling the mixture to roomtemperature, it was poured into intensively stirred cold water (4 l). After 10 min, an orange precipitate was filtered off andwashed with water (2 200 ml). The obtained crude productwas recrystallized from 80percent EtOH and dried under vacuum togive pure 4-bromo-2-nitroaniline (yield 39.9 g, 74percent) as anorange crystalline solid. From the filtrate, a second crystallizationcrop was obtained (yield 6.81 g), comprised of 4-bromo-2-nitroaniline and 2-bromo-6-nitroaniline in a 1:0.3ratio. The NMR spectra are consistent with those published inthe literature (Manley et al., 2003; Lemaire et al., 1989). Analytical data for 4-bromo-2-nitroaniline, 1H NMR(300 MHz, CDCl3): 8.26 (dd, J = 2.3, 0.4 Hz, 1H), 7.42 (dd, J =8.9, 2.3 Hz, 1H), 6.73 (dd, J = 8.9, 0.4 Hz, 1H), 6.10 (s, 2H).Analytical data for 2-bromo-6-nitroaniline, 1H NMR(400 MHz, CDCl3): 8.14 (dd, J = 8.7, 1.5 Hz, 1H), 7.70 (dd, J =7.7, 1.5 Hz, 1H), 6.63 (s, 2H), 6.62 (dd, J = 8.7, 7.7 Hz, 1H).Single crystals of 4-bromo-2-nitroaniline were obtained byslow evaporation from chloroform and of 2-bromo-6-nitroanilineby sublimation of the second crystallization crop underreduced pressure (323 K, 10 mbar; 1 bar = 105 Pa).2-Bromo-6-nitroaniline A mixture of 1-bromo-2-fluoro-3-nitrobenzene (6.0 g, 27.27 mmol) and NHA mixture of l-bromo-2-fluoro-3 -nitrobenzene (20.0 g, 91.37 mmol) and HTo a solution of 2-nitroaniline (34.5 g, 0.25 mol) in aceticacid (400 ml), N-bromosuccinimide (44.5 g, 0.25 mol) wasadded portionwise over a period of 30 min at 308-318 K(Fig. 1). The mixture was stirred for 3 h at 318 K, warmed to363 K and stirred for 2 h. After cooling the mixture to roomtemperature, it was poured into intensively stirred cold water (4 l). After 10 min, an orange precipitate was filtered off andwashed with water (2 200 ml). The obtained crude productwas recrystallized from 80% EtOH and dried under vacuum togive pure 4-bromo-2-nitroaniline (yield 39.9 g, 74%) as anorange crystalline solid. From the filtrate, a second crystallizationcrop was obtained (yield 6.81 g), comprised of 4-bromo-2-nitroaniline and 2-bromo-6-nitroaniline in a 1:0.3ratio. The NMR spectra are consistent with those published inthe literature (Manley et al., 2003; Lemaire et al., 1989). Analytical data for 4-bromo-2-nitroaniline, 1H NMR(300 MHz, CDCl3): 8.26 (dd, J = 2.3, 0.4 Hz, 1H), 7.42 (dd, J =8.9, 2.3 Hz, 1H), 6.73 (dd, J = 8.9, 0.4 Hz, 1H), 6.10 (s, 2H).Analytical data for 2-bromo-6-nitroaniline, 1H NMR(400 MHz, CDCl3): 8.14 (dd, J = 8.7, 1.5 Hz, 1H), 7.70 (dd, J =7.7, 1.5 Hz, 1H), 6.63 (s, 2H), 6.62 (dd, J = 8.7, 7.7 Hz, 1H).Single crystals of 4-bromo-2-nitroaniline were obtained byslow evaporation from chloroform and of 2-bromo-6-nitroanilineby sublimation of the second crystallization crop underreduced pressure (323 K, 10 mbar; 1 bar = 105 Pa).General procedure: Catalytic reaction was carried out in a 50 mL two necked round bottom flask, which charged with 0.05 g of catalyst, substrate (2 mmol) in acetic acid (5 mL) and KBr (2.2 mmol). 30% H2O2 (2.2 mmol) was then added drop wise to the reaction mixture. The content in the flask was stirred continuously at room temperature. After specified time of the reaction, the catalyst was filtered and the solid was washed with ether. The combined filtrates were washed with saturated sodium bicarbonate solution and then shaken with ether in a separating funnel. The organic extract was dried over anhydrous sodium sulfate. The products were analysed by Varian 3400 gas chromatograph equipped with a 30 m CP-SIL8CB capillary column and a Flame Ionization Detector. Identity of the products was also confirmed by using an Agilent GC-MS.Add

Molecular Weight:217.02
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:215.95344
Monoisotopic Mass:215.95344
Topological Polar Surface Area:71.8
Heavy Atom Count:11
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes