2-Bromothiophene has been used in electrochemical reduction of a number of mono- and dihalothiophenes at carbon cathodes in dimethylformamide containing tetramethylammonium per chlorate by cyclic voltammetry and controlled-potential electrolysis.
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Applications
2-Bromothiophene has been used in electrochemical reduction of a number of mono- and dihalothiophenes at carbon cathodes in dimethylformamide containing tetramethylammonium per chlorate by cyclic voltammetry and controlled-potential electrolysis.
Solubility
Not miscible or difficult to mix in water.
Notes
Light Sensitive. Keep away from oxidizing agents. Store in dark.
RUO – Research Use Only
General References:
- Mubarak MS and Peters DG. Electrochemical Reduction of Mono- and Dihalothiophenes at Carbon Cathodes in Dimethylformamide. First Example of an Electrolytically Induced Halogen Dance.J. Org. Chem.,1996,61(23), 8074-8078.
- Peyron C, et al. First example of base-promoted tandem alkylation-bromination of 2-bromothiophene via halogen dance process: a remarkable temperature effect.Tetrahedron Lett.2005,46(19), 3315-3318.
- Sathyapalan A, et al. Novel self assembled monolayers of allyl phenyl thiophene ether as potential dielectric material for organic thin film transistors.Thin Solid Films,2008,516(16), 5645-5648.
- The bromo-substituent can be readily displaced by methoxide in methanol in the presence of a Cu(I) catalyst: Synth. Commun., 20, 213 (1990). For coupling reaction with Thiophene-2-thiol, B22642, in the presence of Cu2O, to give 2,2'-dithienyl sulfide, see: Org. Synth. Coll., 6, 558 (1988).
- Allylic alcohols are thienylated by means of a Heck-type, Pd-catalyzed coupling reaction; the products are ketones formed by rearrangement: Chem. Lett., 423 (1977). Coupling with iodoarenes can be induced at the 5-position by the use of a palladium(II) catalyst in the presence of silver nitrate and potassium fluoride, providing access to 5-aryl-2-bromothiophene derivatives, which may be further elaborated by reaction with the available 2-bromo-substituent: Org. Lett., 7, 5083 (2005).