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The nitro-group is susceptible to nucleophilic displacement (compare 1,4-Dinitrobenzene, A10293): J. Heterocycl. Chem., 18, 1241 (1981). This has been used as the basis of a synthesis of diaryl ethers involving Diels-Alder addition and decarboxylative aromatization of the adduct: J. Chem. Soc., Perkin 1, 1231 (1990):/n
Undergoes vicarious nucleophilic substitution of hydrogen at the 3-position. For example with chloromethyl phenyl sulfone and base, 2-nitro-3-(phenylsulfonylmethyl)furan is formed in 75% yield: Tetrahedron, 51, 8339 (1995). For analogous example and reaction scheme, see 2-Nitrothiophene, A17464./n
For a review of vicarious nucleophilic substitution in heterocyclic compounds, see: Synthesis, 103 (1991)./n
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. 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 IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant