Sodium Bis(2-methoxyethoxy)aluminum Hydride

[22722-98-1] C6H16AlNaO4 (MW 202.19) InChI = 1S/2C3H7O2.Al.Na.2H/c2*1-5-3-2-4;;;;/h2*2-3H2,1H3;;;;/q2*-1;2*+1;; InChIKey = XJIQVZMZXHEYOY-UHFFFAOYSA-N (reducing agent for many functional groups;1 methylation reagent for aryl-activated compounds;19 can function as a base;21 can hydroaluminate alkenes and alkynes22) Alternate Names: SMEAH, Red-Al®, Vitride. Physical Data: fp 4 °C (3.4 M toluene solution); d 1.036 g cm−3 (3.4 M toluene solution), d 1.122 g cm−3 (solid); highly viscous liquid at rt; thermally stable up to 205 °C, upon which vigorous decomposition starts. Solubility: sol aromatic hydrocarbons, ether, THF, DME; insol aliphatic hydrocarbons. Form Supplied in: 3.4 M solution in toluene. 145 g contains 1 mol of active hydride. The pure compound is a slightly yellow, glassy solid. Analysis of Reagent Purity: concentration can be determined by iodometric titration. The titration of SMEAH solutions can be performed using salicylaldehyde phenyl hydrazone,24 using 9H-fluoren-9-one,25 or by NMR spectroscopy, using the No-D 1H NMR-based method.26 Handling, Storage, and Precautions: highly flammable; moisture sensitive; reacts less strongly with H2O than LiAlH4; potent skin irritant. Use in a fume hood.