58367-45-6Relevant academic research and scientific papers
Quantitative Silylation Speciations of Primary Phenylalkyl Amines, Including Amphetamine and 3,4-Methylenedioxyamphetamine Prior to Their Analysis by GC/MS
Molnár, Borbála,Fodor, Blanka,Boldizsár, Imre,Molnár-Perl, Ibolya
, p. 10188 - 10192 (2015/11/09)
A novel, quantitative trimethylsilylation approach derivatizing 11 primary phenylalkyl amines (PPAAs), including amphetamine (A) and 3,4-methylenedioxyamphetamine (MDA), was noted. Triggering the fully derivatized ditrimethylsilyl (diTMS) species with the N-methyl-N-(trimethylsilyl)-trifluoroacetamide (MSTFA) reagent, a new principle was recognized followed by GC/MS. In the course of method optimization, the complementary impact of solvents (acetonitrile, ACN; ethyl acetate, ETAC; pyridine, PYR) and catalysts (trimethylchlorosilane, TMCS; trimethyliodosilane, TMIS) was studied: the role of solvent and catalyst proved to be equally crucial. Optimum, proportional, huge responses were obtained with the MSTFA/PYR = 2/1-9/1 (v/v) reagent applying catalysts; A and MDA needed the TMIS, while the rest of PPAAs provided the diTMS products also with TMCS. Similar to derivatives generated with hexamethyldisilazane and perfluorocarboxylic acid (HMDS and PFCA) (Molnár et al. Anal. Chem. 2015, 87, 848'852), the fully silylated PPAAs offer several advantages. Both of our methods save time and cost by allowing for direct injection of analytes into the column; this is in stark contrast with the requirement to evaporate acid anhydrides by nitrogen prior to their injection. Efficiences of the novel catalyzed trimethylsilylation (MSTFA) and our recently introduced (now, for A and MDA extended) acylation principle were contrasted. Catalyzed trimethylsilylation led to diTMS derivatives resulting in on average a 1.7 times larger response compared to the corresponding acylated species. Catalyzed trimethylsilylation of PPAAs, A, and MDA were characterized with retention, mass fragmentation, and analytical performance properties (R2, LOQ values). The practical utility of ditrimethylsilyation was shown by analyzing A in urine and mescaline (MSC) in cactus samples.
CONTRIBUTIONS TO THE CHEMISTRY OF ORGANIC SILICON-NITROGEN-COMPOUNDS, I. SYNTHESIS OF N,N-BIS-(TRIMETHYLSILYL)AMINES
Schorr, Manfred,Schmitt, Wilfried
, p. 25 - 36 (2007/10/02)
The preparation of N,N-bis-(trimethylsilyl)amines 1 has been investigated.Three convenient methods are reported: A, Transfer of (catalytically) activated Tms-groups to amines starting from N-silylated carbonamides, B, silylation of amines with trimethylsilylchloride 5/NEt3 in the presence of TiCl4, C, silylation of primary amines 4 or mono-(trimethylsilyl)amines 16 with CF3SO3 Tms/NEt3 or TmsI/NEt3.Methods A and B are limited to the silylation of (ar)alkylamines which have no branched α-position. Key words: N,N-bis-(trimethylsilyl)amines; N,N-bis-silylamines; N-silylcarbonamides.
Preliminary communication. Primary aminomethylation of organometallic compounds via N,N-bis(trimethylsilyl)methylthiomethylamine
Fiocca, Luisa,Fiorenza, Mariella,Reginato, Gianna,Ricci, Alfredo,Dembech, Pasquale,Seconi, Giancarlo
, p. C23 - C26 (2007/10/02)
The reaction of various organometallic compounds with N,N-bis(trimethylsilyl)methylthiomethylamine provides an easy way for the introduction of primary aminomethyl unit into a variety of organic substrates.
Silylated Amines II. A New, Highly Variable Amine Synthesis by the N,N-Bis(trimethylsilyl)aminomethylation of Grignard Compounds
Betsmann, Hans Juergen,Woelfel, Gerhard,Mederer, Karl
, p. 848 - 850 (2007/10/02)
Sodium bis(trimethylsilyl)amide reacts with chloromethyl methylether (1) to form methoxy-N,N-bis(trimethylsilyl)aminomethane (3), which effects the aminomethylation of Grignard compounds 4 to form N,N-bis(trimethylsilyl)amines 5.
N,N-Bis(trimethylsilyl)methoxymethylamine as a Convenient Synthetic Equivalent for +CH2NH2: Primary Aminomethylation of Organometallic Compounds
Morimoto, Toshiaki,Takahashi, Toshio,Sekiya, Minoru
, p. 794 - 795 (2007/10/02)
The introduction of the primary aminomethyl unit at carbon through N,N-bis(trimethylsilyl)aminomethylation of Grignard and organolithium compounds can be achieved in good yield using N,N-bis(trimethylsilyl)methoxymethylamine (1).
