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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-H500
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. May form combustible dust concentrations in air
Precautionary Statements: P201-P202-P260-P264b-P270-P271-P281-P301+P310-P302+P352-P304+P340-P308+P313-P311-P312-P330-P361-P363-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Use personal protective equipment as required. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF exposed or concerned: Get medical advice/attention. Call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. Remove/Take off immediately all contaminated clothing. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant