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3-Bromothiophene is used in the preparation of derivatives such as thienylenic alpha, µ-diformyl-alpha-oligothiophenes and 3-lithiothiophene. It is also used in the synthesis of 3-lithiothiophene by reacting with n-butyllithium.
Intermediate for preparation of 3-substituted thiophenes by the Grignard route: Arkiv. Kemi., 13, 295 (1959). Similarly, used in the synthesis of poly(3-alkylthiophenes) as conducting polymers: J. Org. Chem., 58, 904 (1993). Conditions have been described for the formation of 3-lithiothiophene, previously considered to be stable only under cryogenic conditions. It has been found to be stable in hexane solution at ambient temperature: Tetrahedron Lett., 35, 3673 (1994). Subsequent reaction with electrophiles leads to a variety of 3-substituted thiophenes.
Tang, T.; Lin, T.; Wang, F.; He, C. Origin of Near-Infrared Absorption for Azulene-Containing Conjugated Polymers upon Protonation or Oxidation. J. Phys. Chem. B 2014, 119 (25), 8176-8183.
Skhiri, A.; Beladhria, A.; Yuan, K.; Soule, J.; Salem, R. B.; Doucet, H. Pd-Catalysed Direct Arylation of Heteroaromatics Using (Poly)halobenzenesulfonyl Chlorides as Coupling Partners: One Step Access to (Poly)halo-Substituted Bi(hetero)aryls. Eur. J. Org. Chem. 2015, 2015 (20), 4428-4436.
Hazard Statements: H227-H300-H310-H330-H315-H319-H335
Combustible liquid. Fatal if swallowed. Fatal in contact with skin. Fatal if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P301+P310a-P304+P340-P305+P351+P338-P320-P330-P405-P501a
IF SWALLOWED: Immediately call a POISON CENTER/doctor 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. Specific treatment is urgent (see label). Rinse mouth. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.