Trimethylsilyl donor strength approximately equal to BSA
Increased volatility of reaction byproducts mono(trimethylsilyl)trifluoroacetamide and trifluoroacetamide, over corresponding nonfluorinated compounds from BSA
Increased volatility makes it possible to derivatize smaller molecules with which the TMS derivatives elute with the byproducts from BSA
React with the same classes of compounds as BSA, producing the same derivatives
Add TMCS to derivatize amides, many secondary amines and hindered hydroxyls that are not derivatized by BSTFA alone
Applications
Excellent derivatization reagent for analyzing drugs of abuse (THC Metabolites, Morphine and PCP)
Can substitute for BSA in many derivatization techniques
BSTFA is an effective trimethylsilyl donor with donor strength approximately the same as its unfluorinated analog BSA, N,O-bis(trimethylsilyl)acetamide. It reacts with a wide range of polar compounds to replace labile hydrogens on a wide range of polar compounds with a -Si(CH3)3 group. Therefore, it is widely used to prepare volatile and thermally stable derivatives for gas chromatography and mass spectrometry.
One of the particular advantages of BSTFA over many of the other silylating reagents is the volatility of its by-products, mono (trimethylsilyl)trifluoro-acetamide and trifluoroac-etamide. For example, in the gas chromatographic analysis of some of the lower boiling TMS-amino acids and TMS-Krebs cycle acids, the retention times of these derivatives cause them to be co-eluted with the by-products from most TMS derivatization reagents. Good chromatographic separations can be obtained with BSTFA as the by-products from this reagent usually elute with the solvent front.
BSTFA can be used at full strength or diluted with a suitable solvent such as pyridine. In most applications it is advisable to use an excess of the silylating reagent and at least a two to one molar ratio of BSTFA to active hydrogen is recommended. Best results are obtained when the products of the silylation reaction are soluble in the final reaction mixture. Amides, many secondary amines and hindered hydroxyls will not be derivatized by BSTFA alone; however, when a catalyst such as trimethylchlorosilane is added, many of these compounds can be derivatized satisfactorily. A separate instruction book is available which addresses those applications which are best accomplished by the use of a catalyst with BSTFA.
References
1.Bagnati, R., et al. (1996). Analysis of Dexamethasone and betamethasone in bovine urine by purification with an "on-line" immunoaffinity chromatography-high performance liquid chromatography system and determination by gas chromatography-mass spectrometry. Analytical Biochemistry 235, 119. 2.Heinzen, H., et al. (1996). Mass Spectrometry of Labelled Triterpenoids: Thermospray and Electron Impact Ionization Analysis. Phytochemical Analysis 7(5), 237-244. 3.Her, G.R., et al.(1985). Quantitative methodology for corticosteroids based on chemical oxidation using electrophilic products for electron capture-negative chemical ionization using capillary gas chromatography-mass spectrometry. Analytical Biochemistry 151, 292. 4.Le Quéré, V., et al. (2004). Human CYP4F3s are the main catalysts in the oxidation of fatty acid epoxides. J. Lipid Res 45(8), 1446-1458. 5.Nichols, F. C., et al. (2004). Structures and biological activities of novel phosphatidylethanolamine lipids of Porphyromonas gingivalis. J. Lipid Res 45(12), 2317-2330. 6.Shanchun J., et al. (1994). Origins and simulated thermal alteration of sterols and keto-alcohols in deep sea marine sediments of the Okinawa Trough. Organic Geochemistry 21, 415. 7.Yu, L., et al. (2005). Fine organic aerosols collected in a humid, rural location (Great Smoky Mountains, Tennessee, USA): Chemical and temporal characteristics. Atmospheric Environment 39(33), 6037-6050.
1 Artículos Total 7,000.00 USD ![BSTFA (<i>N,O</i>-bis[Trimethylsilyl]trifluoroacetamide)](/com/CMA/Images/Image_47909.jpg)
