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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-H315-H317-H318
Harmful if swallowed. Fatal in contact with skin. Causes skin irritation. May cause an allergic skin reaction. Causes serious eye damage.
Precautionary Statements: P261-P262-P264b-P270-P272-P280-P301+P312-P302+P350-P305+P351+P338-P310-P330-P333+P313-P361-P363-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Gently wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. If skin irritation or rash occurs: Get medical advice/attention. Remove/Take off immediately all contaminated clothing. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant