is used in the Barton–McCombie deoxygenation reaction for deoxygenation of alcohols. In combination with lithium tri-tert-butoxyaluminum hydride it cleaves ethers. For example, THF is converted, after hydrolysis, to 1-butanol. It also promotes certain variants of the Reformatskii reaction. Triethylborane is the precursor to the reducing agents lithium triethylborohydride ("Superhydride") and sodium triethylborohydride. MH + Et3B → MBHEt3 (M = Li, Na) Triethylborane reacts with methanol to form diethyl(methoxy)borane, which is used as the chelating agent in the Narasaka–Prasad reduction for the stereoselective generation of syn-1,3-diols from β-hydroxyketones. Safety Triethylborane is strongly pyrophoric, with an autoignition temperature of , burning with an apple-green flame characteristic for boron compounds. Thus, it is typically handled and stored using air-free techniques. Triethylborane is also acutely toxic if swallowed, with an LD50 of 235 mg/kg in rat test subjects. See also Organoboranes Pentaborane Zip fuel References Alkylboranes Rocket fuels