[13057-19-7] C2H5IO (MW 171.97) InChI = 1S/C2H5IO/c1-4-2-3/h2H2,1H3 InChIKey = UUSXSNJAQDJKCG-UHFFFAOYSA-N (reactive methoxymethylating agent for phosphorus,1 carbon,2 oxygen,3 and nitrogen4 nucleophiles; iodomethylating agent for aromatic systems5) Alternate Name: iodomethoxymethane. Physical Data: bp 122 °C (dec), 39 °C/20 mmHg; d 2.030 g mL−1. Solubility: sol common organic solvents. Form Supplied in: liquid, commercially available (stabilized with copper). Preparative Methods: displacement of chloride from Chloromethyl Methyl Ether by iodide ion, followed by distillation of the product (eq 1);2a,2b,5b reaction of Formaldehyde or trioxane with methanol and Hydrogen Iodide (eq 2);6 reaction of methylal (Dimethoxymethane) with Iodotrimethylsilane (eq 3).1a This last route has the advantage of not using or producing highly carcinogenic materials such as chloromethyl methyl ether or Bis(chloromethyl) Ether. (1) (2) (3) Handling, Storage, and Precautions: corrosive and a lachrymator; a strong alkylating agent and as such is likely to be harmful if swallowed or absorbed through the skin. It should be handled accordingly. Use in a fume hood.