Borane–Triethylamine/Borane–Trimethylamine

Abstract image (Borane–trimethylamine 1 ) [ 75‐22‐9 ] C 3 H 12 BN (MW 72.95) InChI = 1S/C3H9N.BH3/c1‐4(2)3;/h1‐3H3;1H3 InChIKey = WVMHLYQJPRXKLC‐UHFFFAOYSA‐N (Borane–triethylamine) [ 1722‐26‐5 ] C 6 H 18 BN (MW 115.02) InChI = 1S/C6H15N.BH3/c1‐4‐7(5‐2)6‐3;/h4‐6H2,1‐3H3;1H3 InChIKey = KDKNBGWKECQREO‐UHFFFAOYSA‐N (representative of the borane complexes of trialkylamines, mild reductants soluble in most organic solvents, less sensitive to hydrolysis even under acidic conditions than borohydrides or borane–pyridine; used in conjunction with Lewis or Brønsted acids to reduce carbon–oxygen and –nitrogen double bonds as well as indoles and acetals; can be used as borane carriers for olefin hydroboration and to activate carboxylic acids as acylating agents) Borane–trimethylamine Physical Data: mp 94–94.5 °C, bp 171 °C. Solubility: very sol methanol, diethyl ether, THF, toluene, and dichloromethane; sol water; insol hexane. 1 Form Supplied in: colorless solid. Purification: vacuum sublimation. 2 Handling, Storage, and Precautions: hydrolytically stable in neutral or even mildly acidic aqueous solution; 3 thermally stable to 120 °C. 4 Decomposition of excess reagent with aqueous acid 1 generates hydrogen gas. Toxicity (intraperitoneal) rat LD 50 : 175 mg kg −1 . 5