TCI C0220, 2-chloronitrobenzene (CAS 88-73-3), is a classical activated aryl halide in which an ortho nitro group strongly promotes nucleophilic aromatic substitution at the carbon bearing chlorine. It reacts readily with amines, phenoxides, alkoxides, and thiolates to give nitro-substituted diphenylamines, diaryl ethers, and diaryl sulfides that can be cyclised into phenothiazine or carbazole frameworks after nitro reduction. Direct reduction instead provides 2-chloroaniline, itself a valuable intermediate. AMI Scientific stocks this TCI reagent in 25 g and 500 g packs; consult the official product data sheet and SDS before use, as this class of compound can be absorbed through the skin.
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- Arjunan et al. (2012). A comparative spectroscopic, electronic structure and chemical shift investigations of o-Chloronitrobenzene, p-Chloronitrobenzene and m-Chloronitrobenzene. Journal of Molecular Structure doi:10.1016/j.molstruc.2011.10.033
- Guo et al. (2005). Selective adsorption of p-chloronitrobenzene from aqueous mixture of p-chloronitrobenzene and o-chloronitrobenzene using HZSM-5 zeolite. Water Research doi:10.1016/j.watres.2004.12.031
- (1997). 4-Chloronitrobenzene. Environmental Health Perspectives doi:10.2307/3433449
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