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Furan has an important biological properties and pharmacological activity. Its iodinated lipophilic derivative is widely used in the treatment of ventricular and arterial fibrillation. Its derivatives are used as inhibitors of biofilm formation for several bacterial species, as well as possess quorum-sensing inhibitory activities. 2-methylfuran and 2,5-dimethylfuran are used as lignocellulosic biofuels. Its resin is used to stop sand production in underground gas storage wells. It undergo Diels-Alder reaction with arynes to give derivatives of dihydronaphthalenes which are useful intermediates in synthesis of other polycyclic aromatic compounds.
Diels-Alder cycloadditions of furans with reactive dienophiles, followed by dehydration of the resulting 7-oxabicyclo[2.2.1]heptenes generate benzenes, often with unusual substitution patterns; review: Heterocycles, 22, 875 (1984). Adducts of furans with alkynes can be deoxygenated to give aromatics, by reduction with a low-valent Ti reagent: Synthesis, 787 (1984).
Lithiation occurs at the 2-position. For the formation of furfuryl propargyl ethers and their subsequent base catalyzed intramolecular Diels-Alder cyclization to isobenzofuran derivatives, see: J. Org. Chem., 60, 6168 (1995). 2,5-Dilithiation can be effected with n-BuLi - TMEDA: J. Chem. Soc., Perkin 1, 887 (1977), or n-BuLi - KO-t-Bu: Synthesis, 316 (1988). A Barbier-type reaction has been reported in which furan is reacted with a lithium carboxylate in the presence of Li metal and t-butyl chloride with sonication: J. Org. Chem., 60, 8 (1995), providing an easy access to 2-furyl ketones.
García-Gómez, D.; Bregy, L.; Barrios-Collado, C.; Miguel, G. V.; Zenobi, R. Real-Time High-Resolution Tandem Mass Spectrometry Identifies Furan Derivatives in Exhaled Breath. Anal. Chem. 2015, 87 (13), 6919-6924.
Xu, N.; Tang, C.; Meng, X.; Fan, X.; Tian, Z.; Huang, Z. Experimental and Kinetic Study on the Ignition Delay Times of 2,5-Dimethylfuran and the Comparison to 2-Methylfuran and Furan. Energy Fuels 2015, 29 (8), 5372-5381.
Dichiarazioni di rischio (UE): H224-H302-H332-H315-H341-H350-H373
Extremely flammable liquid and vapour. Harmful if swallowed. Harmful if inhaled. Causes skin irritation. Suspected of causing genetic defects. May cause cancer. May cause damage to organs through prolonged or repeated exposure.
Dichiarazioni precauzionali: P210-P260-P201-P303+P361+P353-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.