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Synthesis of deuterium labeled isobutane: isobutane‐2‐d 1 , isobutane‐1‐d 9 and isobutane‐d 10
Author(s) -
Sassi A.,
Coeppert A.,
Sommer J.,
Esteves P. M.,
Mota C. J.
Publication year - 1999
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199911)42:11<1023::aid-jlcr257>3.0.co;2-g
Subject(s) - isobutane , chemistry , yield (engineering) , deuterium , propane , medicinal chemistry , organic chemistry , catalysis , nuclear physics , materials science , physics , metallurgy
Abstract 2‐Methylpropane‐2‐d 1 (isobutane‐2‐d 1 ), 2‐(methyl‐d 3 )‐propane‐1,1,1,3,3,3‐d 6 (nonadeuterated isobutane) and 2‐methylpropane‐d 10 (perdeuterated isobutane) were synthesized by using a combination of classical organic chemistry and recently developed H/D exchange processes on solid acids. Isobutane‐2‐d 1 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‐d 9 was prepared by H/D exchange of 2‐methylpropane (isobutane) with a D 2 O 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‐d 1 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.