1,1,2,3,3-Pentaisopropylguanidine

[81236-11-5] C16H35N3 (MW 269.54) InChI = 1S/C16H35N3/c1-11(2)17-16(18(12(3)4)13(5)6)19(14(7)8)15(9)10/h11-15H,1-10H3 InChIKey = YKRBTEJVESWMGV-UHFFFAOYSA-N (hindered amine base; used in oxidations of ketone hydrazones, and in eliminations of hydrogen iodide and p-toluenesulfonic acid) Preparative Method: the reagent is not commercially available, but is easily prepared in two steps. First, Thiophosgene is slowly added to Diisopropylamine to give N,N,N′,N′-tetraisopropylthiourea, as a pale yellow liquid, in 44% yield. A Vilsmeier salt is then formed from the reaction of tetraisopropylthiourea with Phosgene, and subsequently treated with isopropylamine to give 1,1,2,3,3-pentaisopropylguanidine (69% yield) as a liquid, bp 60 °C/0.01 mmHg (eq 1).1 The compound solidifies on storing at −20 °C under argon. (1) Handling, Storage, and Precautions: Use in a fume hood.