CAS 14041-29-3, Cat. No EN300-54108642
Reagent for thiolation
4-((tert-Butylthio)methyl) morpholine is a member of the dialkylaminomethyl sulfide class1. Like related aminomethyl sulfides (e.g., methyl analog EN300-53983882), it exists in equilibrium with an iminium/thiolate pair and can therefore serve as a controlled thiolate-transfer reagent, releasing tert-butylthiolate in low steady-state concentration. This controlled release prevents catalyst poisoning and enables its use as an odor-reduced, bench-stable sulfur transfer reagent for C–S bond formation under metal-catalyzed coupling conditions2. The reagent shows broad compatibility with aryl electrophiles (aryl chlorides, bromides, triflates, and related substrates) and tolerates functional groups such as esters, ketones, aldehydes, heterocycles, and halides. Sterically hindered substrates react more slowly, reflecting the bulky tert-butylthiolate fragment.
Synonyms: tert-butylthiomethyl morpholine; 4-[(tert-butylsulfanyl)methyl]morpholine; 4-[[(1,1-dimethylethyl)thio]methyl]morpholine; morpholine, 4-[(tert-butylthio)methyl]-
Selected publication
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Dialkylaminomethyl Sulfides: An Improved Synthesis.
Vineyard, B. D. J. Chem. Eng. 1966, 11 (4), 620–621. DOI: 10.1021/je60031a057
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Metal-Catalyzed Methylthiolation of Chloroarenes and Diverse Aryl Electrophiles.
Toyoda, S.; Iizumi, K.; Yamaguchi, J. Chem. Sci. 2025, 16 (25), 11559–11567. DOI: 10.1039/D5SC01428J