O-Benzylhydroxylamine Hydrochloride

(base) [622-33-3] C7H9NO (MW 123.15) InChI = 1S/C7H9NO/c8-9-6-7-4-2-1-3-5-7/h1-5H,6,8H2 InChIKey = XYEOALKITRFCJJ-UHFFFAOYSA-N (·HCl) [2687-43-6] C7H10ClNO (MW 159.62) InChI = 1S/C7H9NO.ClH/c8-9-6-7-4-2-1-3-5-7;/h1-5H,6,8H2;1H InChIKey = HYDZPXNVHXJHBG-UHFFFAOYSA-N (reagent for the preparation of N-hydroxyamides2 (including N-hydroxy peptides3 and N-hydroxy β-lactams4) and hydroxamic acids;5 derivatizing agent for ketones,6-8 aldehydes,6 and carbohydrates9) Alternate Names: O-phenylmethylhydroxylamine hydrochloride; benzyloxyamine hydrochloride; benzyloxyammonium chloride. Physical Data: white flakes, mp 234–238 °C (subl); hygroscopic. Solubility: sol H2O, pyridine; slightly sol alcohol; insol ether. Analysis of Reagent Purity: 1H NMR (DMSO-d6 + CDCl3) δ 5.17 (s, 2H, CH2), 7.42 (s, 5H, C6H5), 11 (br, ex NH2). Preparative Methods: the free base O-benzylhydroxylamine, a liquid of bp 115–119 °C/30 mmHg, is easily prepared from the commercially available hydrochloride salt.10 For many reactions, however, it is preferable to generate the free base in situ from the salt. Handling, Storage, and Precautions: store in a cool dry place to preclude contact with moisture and oxygen; may be harmful by inhalation, ingestion, or skin absorption; avoid contact with the eyes.