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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.
Hazard Statements: H224-H302-H315-H319-H332-H341-H350-H373
Extremely flammable liquid and vapour. Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. Harmful if inhaled. Suspected of causing genetic defects. May cause cancer. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P201-P202-P210-P233-P240-P241-P242-P243-P260-P264b-P270-P271-P280i-P281-P301+P312-P303+P361+P353-P304+P340-P305+P351+P338-P308+P313-P330-P332+P313-P337+P313-P363-P370+P378q-P5
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. 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. Wear eye/face protection. Use personal protective equipment as required. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. 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. IF exposed or concerned: Get medical advice/attention. Rinse mouth. If skin irritation occurs: If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam