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

Boiling point:

172-175 °C(lit.)

Density 

1.036 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.402(lit.)

Flash point:

127 °F

storage temp. 

2-8°C

solubility 

sol most aprotic organic solvents.

pka

-1.50±0.70(Predicted)

form 

Liquid

Specific Gravity

1.023

color 

Clear colorless to slightly yellow

Water Solubility 

decomposes

Sensitive 

Moisture Sensitive

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

BRN 

3606546

CAS DataBase Reference

77377-52-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

10-36/37/38

Safety Statements 

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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide Usage And Synthesis

Chemical Properties

clear colorless to slightly yellow liquid

Physical properties

bp 168–170°C; d 1.12 g cm?3.

Uses

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.

Uses

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.

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.

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.

Definition

ChEBI: An N-silyl compound that is N-methyltrifluoroacetamide in which the amide nitrogen is replaced by a tert-butyldimethylsilyl group.

General Description

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.

N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide(77377-52-7)Related Product Information

• METSULFURON METHYL
• Basic Violet 1
• Trifluoroacetamide
• N-Methylacetamide
• N,N-Dimethylformamide
• N,N-Dimethylacetamide
• Methyl acrylate
• Tribenuron methyl
• POLYDIMETHYLSILOXANE
• Kresoxim-methyl
• Methylparaben
• Dimethyl sulfoxide
• Methyl salicylate
• Dimethyl sulfone
• Methanol
• Poly(dimethylsiloxane)
• tert-Butyldimethylsilyl chloride
• Methyl