TCI C1186 tert-Butyl Crotonate (CAS 79218-15-8) is an α,β-unsaturated ester in which the bulky tert-butyl group serves as an acid-labile ester protecting group. Its conjugated double bond makes it a useful Michael acceptor and dienophile, while the steric bulk helps direct nucleophilic attack toward the beta position. The ability to remove the tert-butyl group under acidic conditions makes it attractive for orthogonal protection strategies in multistep synthesis. Supplied in a 25 mL pack, it should be handled in a fume hood and stored cool and tightly closed, away from strong acids, heat, and radical initiators.
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- Ute et al. (1996). Highly “Diheterotactic” Polymerization of tert-Butyl Crotonate. Macromolecules doi:10.1021/ma951275f
- Kraehenbuehl et al. (1994). Vapor Pressures of Methyl tert-Butyl Ether, Ethyl tert-Butyl Ether, Isopropyl tert-Butyl Ether, tert-Amyl Methyl Ether, and tert-Amyl Ethyl Ether. Journal of Chemical & Engineering Data doi:10.1021/je00016a026
- Krossing et al. (2008). Dimeric Di(tert-butyl)haloalanes and a Monomeric Di(tert-butyl)phosphino-di(tert-butyl)alane. Zeitschrift für Naturforschung B doi:10.1515/znb-2008-0905
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