O ‐Pivaloyl Hydroxylamine Triflic Acid

[1293990-73-4] C6H12F3NO5S (MW 267.22) InChI = 1S/C5H12NO2.CHF3O3S/c1-5(2,3)4(7)8-6;2-1(3,4)8(5,6)7/h1-3,6H3;(H,5,6,7)/q+1;/p-1 InChIKey = AJUKGKFBUGZGSW-UHFFFAOYSA-M (easy-to-handle reagent for the installation of an O-acylated hydroxylamine motif1 and as reagent in electrophilic amination reactions to directly access unprotected anilines,2,3 primary amines,4–7 and aminosulfur compounds8,9) Alternative Name: O-Pivaloylhydroxylammonium trifluoromethanesulfonate. Physical Data: mp 139–141 °C. Solubility: insoluble in pentane and DCM. Soluble in acetonitrile and methanol (>3 g mL−1). Slow decomposition in DMSO. Form Obtained in: colorless, free-flowing solid or needles (after recrystallization); not commercial. Analysis of Reagent Purity: 1H NMR and elemental analysis. Preparative Methods: Prepared through a two-step process. Starting from N-Boc hydroxylamine, O-pivaloylation and subsequent Boc-deprotection with triflic acid affords reagent 1 as colorless precipitate (eq 1). Purification of the protected intermediate or the product is usually not required. See the literature for a detailed procedure.10 (1) Purification: recrystallization from n-butyl acetate. Handling, Storage, and Precautions: bench- and air-stable solid. May absorb water from the atmosphere. For long-term storage, <10 °C is recommended. Decomposes exothermally at 192 °C.5