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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-H319
Highly flammable liquid and vapour. Harmful if swallowed. Causes serious eye irritation.
Precautionary Statements: P210-P233-P240-P241-P242-P243-P264b-P270-P280-P301+P312-P303+P361+P353-P305+P351+P338-P330-P337+P313-P370+P378q-P501c
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. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. 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 (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. Rinse mouth. If eye irritation persists: Get medical advice/attention. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant