N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide

Bezeichnung:N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide

CAS-Nr77377-52-7

Englisch Name:N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide

CBNumberCB7707814

SummenformelC9H18F3NOSi

Molgewicht241.33

MOL-Datei77377-52-7.mol

N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide physikalisch-chemischer Eigenschaften

Siedepunkt	172-175 °C(lit.)
Dichte	1.036 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.402(lit.)
Flammpunkt	127 °F
storage temp.	2-8°C
Löslichkeit	sol most aprotic organic solvents.
Aggregatzustand	Liquid
pka	-1.50±0.70(Predicted)
Wichte	1.023
Farbe	Clear colorless to slightly yellow
Wasserlöslichkeit	decomposes
Sensitive	Moisture Sensitive
Hydrolytic Sensitivity	8: reacts rapidly with moisture, water, protic solvents
BRN	3606546
CAS Datenbank	77377-52-7(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,F
R-Sätze:	10-36/37/38
S-Sätze:	26-36-16-37/39-36/37/39
RIDADR	UN 1993 3/PG 3
WGK Germany	3
F	10-21
Hazard Note	Flammable
TSCA	No
HS Code	2931 90 00
HazardClass	3
PackingGroup	III

Gefahreninformationscode (GHS)

N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R10:Entzündlich.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
clear colorless to slightly yellow liquid
Physikalische Eigenschaften
bp 168–170°C; d 1.12 g cm?3.
Verwenden
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.
Verwenden
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.
Verwenden
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.
synthetische
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.
Definition
ChEBI: An N-silyl compound that is N-methyltrifluoroacetamide in which the amide nitrogen is replaced by a tert-butyldimethylsilyl group.
Allgemeine Beschreibung
N-tert-Butyldimethylsilyl-N-methyltrifluoroacetamide is a silylating reagent which replaces the active hydrogen with tert-Butyldimethylsilyl group. The tert-Butyldimethylsilyl derivatives are found to be more resistant to hydrolysis and stable compared to trimethylsilyl (TMS) derivatives. This reagent is suitable for GC-MS analysis since it produces mass spectra, which can be easily interpreted. It is widely used for the silylation of different alcohols, thiols, phenols, carboxylic acids, amines, and amides.
reaction suitability
reagent type: derivatization reagent
reaction type: Silylations

N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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