title: Trimethylsilyldiazomethane: a safe non-explosive, cost effective and less-toxic reagent for phenol derivatization in GC applications.
abstract: Diazomethane is a highly explosive and toxic gas routinely employed for the quantitative and clean derivatization of phenols. We investigated the commercially available trimethylsilyldiazomethane in the presence of diisopropylethylamine as a safe, non-explosive and less-toxic alternative using six phenolic polychlorinated biphenyls as model analytes and fluoro-tagged analogues as internal standards. We compared yields and derivatization times of each method employing a liver microsomal extract as a real matrix. Steric hindrance and electronic properties of the analytes were also investigated. The alternative method afforded equal to higher derivatization yields with increased reaction times, up to 100 min, while explosion and toxic exposure risks were minimized and cost efficiency was increased above 25%. These findings demonstrate that non-explosive trimethylsilyl diazomethane produces comparable derivatization results to the dangerous diazomethane under the conditions studied.
authors.affiliation: Department of Occupational and Environmental Health, University of Iowa, Iowa City, IA, United States.
authors.forename: T J
authors.initials: TJ
authors.lastname: van 't Erve
authors.forename: R H
authors.initials: RH
authors.lastname: Rautiainen
authors.forename: L W
authors.initials: LW
authors.lastname: Robertson
authors.forename: G
authors.initials: G
authors.lastname: Luthe
mesh_terms: D002621:Chemistry / Q000191:economics* / Q000379:methods*; D003978:Diazomethane / Q000031:analogs & derivatives* / Q000737:chemistry / Q000191:economics; D007202:Indicators and Reagents / Q000737:chemistry / Q000191:economics; D009153:Mutagens / Q000138:chemical synthesis / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D011078:Polychlorinated Biphenyls / Q000138:chemical synthesis / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry* / Q000191:economics*
chemical_list: D007202:Indicators and Reagents; D009153:Mutagens; D010636:Phenols; D014297:Trimethylsilyl Compounds; D003978:Diazomethane; D011078:Polychlorinated Biphenyls; C060070:trimethylsilyldiazomethane
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