Chemical Properties
2-Bromo-6-chloro-4-nitroaniline is a pale yellow to yellow or orange powder or crystal with a melting point of 176-178° C. Store at room temperature, protected from light and under inert gas.
Uses
2-Bromo-6-chloro-4-nitroaniline is an organic amine compound that can be used in gas chromatography for analytical determinations, as well as for hydrogen bonding in C-substituted nitroanilines: simpleC(8) chain studies in 2-bromo-6-chloro-4-nitroaniline
[1-2].
Synthesis
General procedure for the synthesis of 2-chloro-4-nitro-6-bromoaniline from 2-chloro-4-nitroaniline: 345 mg (2 mmol) of 2-chloro-4-nitroaniline and 143 mg (1.2 mmol) of potassium bromide were dissolved in 10 mL of a solvent mixture of acetic acid (AcOH) and water (AcOH:H2O = 9:1), and transferred to a 50 mL three-neck flask. The reaction system was placed in a thermostatic magnetic stirring water bath and the reaction temperature was controlled at 50 °C. The reaction mixture was stirred at 30 °C for 1 h. 1.8 g (1.8 mmol) of ZnAl-BrO3-LDHs was added slowly in batches over 15 min before the reaction started. after the reaction was completed, the reaction solution was extracted with dichloromethane and the organic phases were combined. Silica gel (200-300 mesh) was added to the organic phase for adsorption, followed by distillation under reduced pressure to remove the dichloromethane. The residue was purified by column chromatography using a solvent mixture of petroleum ether and ethyl acetate (petroleum ether:ethyl acetate= 10:1) as eluent to give 478 mg of pure product. The product was a yellow solid in 95% yield.
References
[1] D A TELICHKO; V V V; E G Ivaniuk. [Gas chromatography methods of the measurement of concentrations of 2-bromo-6-chloro-4-nitroaniline, N,N-dioxyethyl-M-chloroaniline, N-oxyethyl-N-beta-cyanoethylaniline and N-ethyl-N-beta-cyanoethyl-M-toluidine in the working zone air].[J]. Gigiena truda i professional’nye zabolevaniia, 1990.
[2] CHRISTOPHER GLIDEWELL. Hydrogen bonding in C-substituted nitroanilines: simple C(8) chains in 2-bromo-6-chloro-4-nitroaniline.[J]. Acta crystallographica. Section C, Crystal structure communications, 2005. DOI:10.1107/S0108270105010085.
