77377-52-7 Usage
Description
N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide, also known as BSMTFA, is a highly reactive silylating reagent used in the derivatization of various organic compounds for gas chromatography-mass spectrometry (GC-MS) analysis.
Uses
Used in Chemical Analysis:
BSMTFA is used as a silylating agent for the derivatization of organic compounds, such as amino acids, in gas chromatography-mass spectrometry (GC-MS) analysis. It helps in improving the volatility, stability, and detectability of these compounds.
Used in Organic Chemistry:
In the presence of 1% t-butyldimethylchlorosilane as a catalyst, BSMTFA functions as an extremely reactive t-butyldimethylsilylating reagent for alcohols, amines, carboxylic acids, and thiols. Silylation is generally completed within 5 minutes at 25°C in acetonitrile, making it a more reactive alternative to N-(t-butyldimethylsilyl)-N-methylacetamide.
Used in Protection of Hydroxy Groups:
BSMTFA is used for the protection of hydroxy groups, resulting in the formation of stable t-butyldimethylsilyl (TBDMS) ethers. These ethers remain intact under conditions for acetate saponification and hydrogenation, and are approximately 10 times more stable against hydrolysis than the corresponding trimethylsilyl (TMS) ethers.
Used in Selective Removal of TBDMS Group:
Selective removal of the TBDMS group can be accomplished by using dilute acetic acid or tetra-n-butylammonium fluoride in THF at 25°C.
Used in Silylation of Ketones:
Silylation of ketones using BSMTFA occurs in triethylamine and DMF at 40-60°C to give the corresponding silyl enol ethers in good to excellent yields.
Used in Synthesis of N-tert-Butyldimethylsilyl Ethanolamines:
BSMTFA with 1% tert-butyldimethylchlorosilane is commonly used for the preparation of N-tert-butyldimethylsilyl ethanolamines resulting from the hydrolysis of nitrogen mustards.
Used in Selective O-Silylation:
BSMTFA is also used for selective O-silylation of N,O-diacylhydroxyl amines.
Preparation
obtained in 91% yield by reaction of
N-methyl-2,2,2-trifluoroacetamide (1.0 equiv) in benzene and
acetonitrile (1:1 v/v) with NaH (1.0 equiv) and then with
t-BuMe2SiCl (1.2 equiv) at 4°C.
Check Digit Verification of cas no
The CAS Registry Mumber 77377-52-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,7,3,7 and 7 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 77377-52:
(7*7)+(6*7)+(5*3)+(4*7)+(3*7)+(2*5)+(1*2)=167
167 % 10 = 7
So 77377-52-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H18F3NOSi/c1-5-6-7-15(3,4)13(2)8(14)9(10,11)12/h5-7H2,1-4H3
