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Thiophene is an important building block in dyes, agrochemicals and pharmaceuticals synthesis. It is involved in the chloroalkylation reactions in 2,5-positions. It is also used to prepare butane by reduction with raney nickel, 2-vinylthiophene, dithienyl, and 2-halo thiophenes by reacting with halogens.
Metallation at the 2-position occurs readily with n-BuLi in ether (not readily in benzene). The 2,5-dilithio-derivative can be prepared in the presence of TMEDA: J. Chem. Soc., Perkin 1, 887 (1977), or with the superbasic combination of n-BuLi with KO-t-Bu: Synthesis, 316 (1988).
Smith, Z. C.; Meyer, D. M.; Simon, M. G.; Staii, C.; Shukla, D.; Thomas III, S. W. Thiophene-Based Conjugated Polymers with Photolabile Solubilizing Side Chains. Macromolecules 2015, 48 (4), 959-966.
Ghosh, T.; Gopal, A.; Saeki, A.; Seki, S.; Nair, V. C. p/n-Polarity of thiophene oligomers in photovoltaic cells: role of molecular vs. supramolecular properties. Phys. Chem. Chem. Phys. 2015, 17 (16), 10630-10639.
Hazard Statements: H225-H302-H312-H331-H315-H319
Highly flammable liquid and vapour. Harmful if swallowed. Harmful in contact with skin. Toxic if inhaled. Causes skin irritation. Causes serious eye irritation.
Precautionary Statements: P210-P261-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.