Synthesis of deuterium labeled isobutane: isobutane-2-d1, isobutane-1-d9 and isobutane-d10

2-Methylpropane-2-d1 (isobutane-2-d1), 2-(methyl-d3)-propane-1,1,1,3,3,3-d6 (nonadeuterated isobutane) and 2-methylpropane-d10 (perdeuterated isobutane) were synthesized by using a combination of classical organic chemistry and recently developed H/D exchange processes on solid acids. Isobutane-2-d1 was synthesized from t-butyl chloride by Grignard synthesis with an overall yield of 27.0% (chemical purity : 99.9% and isotopic purity : 96.0%). Isobutane-1-d9 was prepared by H/D exchange of 2-methylpropane (isobutane) with a D2O exchanged zeolite. The deuteriated product was obtained with an overall yield of 80.0% (chemical purity : 99.9% and isotopic purity : 98.7%). Perdeuteriated isobutane was prepared by reacting isobutane-2-d1 with 98.0% deuteriated sulfuric acid and was obtained in a total yield of 98.0% (chemical purity : 99.8% and isotopic purity : 97.9%). Copyright © 1999 John Wiley & Sons, Ltd.