5-Bromothiophenesulfonyl chloride

Chemical Properties

light yellow crystalline low melting solid

Uses

5-Bromothiophene-2-sulfonyl chloride serves as a starting material for the synthesis of sulfonamide compounds[1]. The reagent reacts with 4-chloroanisole to yield the corresponding sulfone product, and couples with 2-aminobenzoic acid in acetone at room temperature using DMAP[1][3]. It functionalizes m-THPP via sulfonate linkers in dry THF with K2CO3, where base selection and temperature control the distribution of mono- and tetrasubstituted derivatives[2]. The compound acts as a sulfonylating agent in dichloromethane with triethylamine, and reacts with glycine tert-butyl ester hydrochloride in a dioxane/water mixture containing Et3N[4][5].

References

[1] Liu, J.-P., Zheng, Y.-B. (2007). 5-Bromothiophene-2-sulfonic acid. Acta Crystallographica Section E Structure Reports Online, 63(9), o3697–o3697. https://doi.org/10.1107/s1600536807037208
[2] Shaker, Y. M., Omar, M. A., Grover, N., Senge, M. O. (2022). Facile synthesis of porphyrin-conjugates as amphiphilic modified photosensitizer structures of m-THPP bearing carbamate, carboxylate and sulfonate linkers. Journal of Porphyrins and Phthalocyanines, 26(10), 638–647. https://doi.org/10.1142/s1088424622500468
[3] Garzya, V., Forbes, I. T., Lauru, S., Maragni, P. (2004). Indium(III)-catalysed aryl sulfonylation reactions. Tetrahedron Letters, 45(7), 1499–1501. https://doi.org/10.1016/j.tetlet.2003.12.028
[4] Dai, Z., Yang, X., Li, Y., Bai, C., Wang, K., Huang, J., Wen, X., Wu, X., Ding, J., Peng, T., He, Y. (2026). Discovery and synthesis of phenylthiophene sulfonamide derivatives with promising anti-inflammatory activity. RSC Advances, 16(37), 40019–40034. https://doi.org/10.1039/d6ra03406c
[5] Nuti, E., Casalini, F., Santamaria, S., Gabelloni, P., Bendinelli, S., Pozzo, E. D., Costa, B., Marinelli, L., Pietra, V. L., Novellino, E., Bernardo, M. M., Fridman, R., Settimo, F. D., Martini, C., Rossello, A. (2011). Synthesis and biological evaluation in U87MG glioma cells of (ethynylthiophene)sulfonamido-based hydroxamates as matrix metalloproteinase inhibitors. European Journal of Medicinal Chemistry, 46(7), 2617–2629. https://doi.org/10.1016/j.ejmech.2011.03.033