N-(tert-Butyldimethylsilyl)-N-methyltrifluoroacetamide

Base Information

• Chemical Name: N-(tert-Butyldimethylsilyl)-N-methyltrifluoroacetamide
• CAS No.: 77377-52-7
• Molecular Formula: C9H18F3NOSi
• Molecular Weight: 241.329
• Hs Code.: 2931 90 00
• DSSTox Substance ID: DTXSID50998589
• Nikkaji Number: J208.101F
• Wikidata: Q27158309
• Mol file: 77377-52-7.mol

Synonyms:MTBSTFA;N-(tert-butyldimethylsilyl)-N-methyltrifluoroacetamide;N-methyl-N-(tert-butyldimethylsilyl)trifluoroacetamide

Chemical Property of N-(tert-Butyldimethylsilyl)-N-methyltrifluoroacetamide

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 0.517mmHg at 25°C
• Refractive Index: n20/D 1.402(lit.)
• Boiling Point: 182.6 °C at 760 mmHg
• PKA: -1.50±0.70(Predicted)
• Flash Point: 64.2 °C
• PSA: 20.31000
• Density: 1.032 g/cm³
• LogP: 3.01230
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: sol most aprotic organic solvents.
• Water Solubility.: decomposes
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 241.11097522
• Heavy Atom Count: 15
• Complexity: 255

Purity/Quality:

99.9% ^*data from raw suppliers

N-(t-Butyldimethylsilyl)-N-methyltrifluoroacetamide 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 26-36-16-37/39-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Silicon)
• Canonical SMILES: CC(C)(C)[Si](C)(C)N(C)C(=O)C(F)(F)F
• Physical properties: bp 168–170°C; d 1.12 g cm?3.
• Uses: N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide is a silylating agent used in the derivatization of various organic compounds (such as amino acids) for gas chromatogography-mass spectrometry (GC-MS) analysis. In the presence of 1% of t-butyldimethylchlorosilane as the catalyst, N-(t-butyldimethylsilyl)-N-methyltrifluoroacetamide (BSMTFA) functions as an extremely reactive t-butyldimethylsilylating reagent for alcohols, amines, carboxylic acids, and thiols. Silylation is generally completed within 5 min at 25°C in acetonitrile. This amide is more reactive than N-(t-butyldimethylsilyl)-N-methylacetamide. In the protection of a hydroxy group, the resultant tbutyldimethylsilyl (TBDMS) ethers are stable under the conditions for acetate saponification and hydrogenation.These silyl ethers also remain intact towards the Jones reagent and Wittig reagents. The TBDMS ethers are approx. 10 times more stable against hydrolysis than the corresponding trimethylsilyl (TMS) ethers.Selective removal of the TBDMS group can be accomplished by use of dilute acetic acid or tetra-n-butylammonium fluoride in THF at 25°C. Silylation of ketones by use ofBSMTFAoccurs in triethylamine and DMF at 40–60°C to give the corresponding silyl enol ethers in good to excellent yields (eq 1).In addition, silyl ether formation takes place in N-hydroxysuccinimide (88% yield) and Nhydroxypyrrole (99% yield) by use of BSMTFA in THF. N-tert-Butyldimethylsilyl-N-methyltrifluoroacetamide with 1% tert-butyldimethylchlorosilane is commonly used for the preparation of N-tert-butyldimethylsilyl ethanolamines resulting from the hydrolysis of nitrogen mustards. It is also used for selective O-silylation of N,O-diacylhydroxyl amines.

Technology Process of N-(tert-Butyldimethylsilyl)-N-methyltrifluoroacetamide

There total 1 articles about N-(tert-Butyldimethylsilyl)-N-methyltrifluoroacetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-methyl-2,2,2-trifluoroacetamide (815-06-5) + tert-butyldimethylsilyl chloride (18162-48-6) → N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide (77377-52-7)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) benzene, acetonitrile, 4 deg C, 4 h, 2.) 2 h;

DOI:10.1021/jo00138a032

Reference yield: 100.0%

N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide (77377-52-7) + N-tert-butoxycarbonyl-(S)-3-chloro-4-hydroxyphenylglycine benzyl ester (436849-00-2) → N-tertbutoxycarbonyl-(S)-3-chloro-4-(tert-butyldimethylsilyloxy)phenylglycine benzyl ester (436849-01-3)

Guidance literature:

In tetrahydrofuran; at 40 ℃; for 3h;

DOI:10.1021/ja020237q DOI:10.1021/ja0212314

Reference yield: 100.0%

salicylic alcohol (90-01-7) + N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide (77377-52-7) → 1-(tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)benzene (82112-31-0)

Guidance literature:

With tert-butyldimethylsilyl chloride; In acetonitrile; for 0.0833333h; Ambient temperature; other silylating agent;

DOI:10.1021/jo00138a032

upstream raw materials:

N-methyl-2,2,2-trifluoroacetamide

tert-butyldimethylsilyl chloride

Downstream raw materials:

(tert-Butyl-dimethyl-silanyl)-[1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-amine

1-(tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)benzene

C₂₁H₃₆O₄Si₂

dibenzyl (S)-2-(tert-butyldimethylsilylamino)succinate