Tributylphosphine

[998-40-3] C12H27P (MW 202.36) InChI = 1S/C12H27P/c1-4-7-10-13(11-8-5-2)12-9-6-3/h4-12H2,1-3H3 InChIKey = TUQOTMZNTHZOKS-UHFFFAOYSA-N (1,4-addition catalyst; used with disulfides for the thioetherification of alcohols; acylation catalyst; used to prepare active esters) Physical Data: bp 240 °C; bp 130 °C/20 mmHg; d 0.812 g cm−3. Solubility: sol most organic solvents; slightly sol MeCN, H2O. Form Supplied in: widely available, neat; usually requires distillation. Analysis of Reagent Purity: 31P NMR.1 Purification: distillation at reduced pressure. Improperly stored bottles of Bu3P are invariably contaminated with tributylphosphine oxide and butyl dibutylphosphinate. Handling, Storage, and Precautions: can be stored at room temperature indefinitely under an inert atmosphere. Oxygen should be rigorously excluded to avoid free radical chain oxidation. Tributylphosphine is pyrophoric and has an unpleasant odor. Toxicity: LD50 (rat) 750 mg kg−1.2