Nitrous acid, tris(1-methylethyl)silyl Ester

Abstract

[61209-09-4] C9H21NO2Si (MW 203.35) InChI = 1S/C9H21NO2Si/c1-7(2)13(8(3)4,9(5)6)12-10-11/h7-9H,1-6H3 InChIKey = RRZPPUDARIQSBT-UHFFFAOYSA-N (oxidant1; reagent for nitrosation and oximation1; silyl nitrite1) Physical Data: liquid, bp 40.5–41.5 °C/1.9 mbar.2 Form Supplied in: commercially not available and mostly prepared in situ prior to use. Analysis of Reagent Purity: NMR, IR, Mass spectroscopy, and elemental analysis.2 Preparative Method: best prepared in situ by the combination of triisopropylsilyl chloride (TIPSCl) with silver nitrite in organic solvent at low temperature (−20 °C).1 First isolation was accomplished by stirring a mixture of silver nitrite (1.22 equiv) and triisopropylsilyl iodide (1.0 equiv) in THF (130 mL) at room temperature for 8 h. The title compound was purified by distillation under reduced pressure after filtering out silver iodide.2 Handling, Storage, and Precautions: toxicity of this chemical is unknown. However, considering cardiac toxicity of nitroso agents, it should be handled excluding direct exposure to light under well-ventilated fume hood. To prevent decomposition, it is necessary to keep cold under inert atmosphere.