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1-Chloro-4-nitrobenzene is an important intermediate used in the preparation of 2,4-dinitrochlorobenzene and 3,4-dichloronitrobenzene. It is used as a raw material in the preparation of 4-nitrodiphenylamine, 4-chloroaninline and (4-[(4-aminobenzene)sulfonyl]aniline). It serves as a common antioxidant, which is found in rubber.
The Cl substituent is activated to nucleophilic substitution by the p-nitro-group, and can be displaced under relatively mild conditions. For displacement by phenoxide, see: Org. Synth. Coll., 2, 445 (1943). For displacement by alkoxide in good yield, in the presence of TBAB or 18-crown-6, see: J. Org. Chem., 48, 3022 (1983).
Büldt, L. A.; Prescimone, A.; Neuburger, M.; Wenger, O. S. Photoredox Properties of Homoleptic d6 Metal Complexes with the Electron-Rich 4,4',5,5'-Tetramethoxy-2,2'-bipyridine Ligand. Eur. J. Inorg. Chem. 2015, 2015 (28), 4666-4677.
Zhuo, L.; Kou, K.; Yao, P.; Wu, G.; Wang, Y. Preparation and thermal decomposition kinetics research of pyridine-containing polyimide. J. Therm. Anal. Calorim. 2015, 119 (3), 2039-2051.
Hazard Statements: H301-H311-H331-H341-H351-H373
Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Suspected of causing genetic defects. Suspected of causing cancer. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P260-P201-P280-P301+P310a-P405-P501a
Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER/doctor Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.