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1-Chloro-2,4-dinitrobenzene is used as a reagent for the detection and determination of pyridine compounds. It has been used as alkylating agent to evaluate the depletion of intracellular erythrocyte glutathione (GSH). It is an irreversible inhibitor of human thioredoxin reductase.
Elias S. J. Arner; Mikael Bjornstedt and Arne Holmgren. 1-Chloro-2,4-dinitrobenzene Is an Irreversible Inhibitor of Human Thioredoxin Reductase. Loss of thioredoxin disulfide reductase activity is accompanied by a large increase in nadph oxidase activity.Journal of Biological Chemistry.1995, 270 3479-3482.
YC Awasthi; HS Garg; DD Dao; CA Partridge and SK Srivastava. Enzymatic conjugation of erythrocyte glutathione with 1-chloro-2,4-dinitrobenzene: the fate of glutathione conjugate in erythrocytes and the effect of glutathione depletion on hemoglobin. bloodjournal.hematologylibrary.1981, 58 733-738.
The doubly-activated chloro-substituent is readily displaced by nucleophiles, e.g.:
Ammonia/ ammonium acetate to give 2,4-dinitroaniline: Org. Synth. Coll., 2, 221 (1943); or with ammonia gas in toluene in the presence of TBAB which improves the solubility of ammonia in the organic medium and accelerates the reaction: J. Chem. Soc., Chem. Commun., 1267 (1987). Benzyl mercaptan to give the thioether: Org. Synth. Coll., 5, 474 (1973). Iodide ion to give 2,4-dinitro-1-iodobenzene: Org. Synth. Coll., 5, 478 (1973). Nitrite in toluene (phase-transfer) to give 1,2,4-trinitrobenzene (caution!): J. Org. Chem., 56, 4967 (1991).
Hazard Statements: H302-H310-H331-H373
Harmful if swallowed. Fatal in contact with skin. Toxic if inhaled. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P260-P262-P280h-P304+P340-P405-P501a
Do not breathe dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. Wear protective gloves/clothing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.