N-Methyl-N-(trimethylsilyl)acetamide Chemical Properties

Boiling point:

159-161 °C(lit.)

Density 

0.904 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.439

Flash point:

48 °C

storage temp. 

-20°C

form 

lyophilized powder

pka

-0.11±0.70(Predicted)

color 

Clear light yellow

Specific Gravity

0.906

Sensitive 

Moisture Sensitive

BRN 

506975

InChI

InChI=1S/C6H15NOSi/c1-6(8)7(2)9(3,4)5/h1-5H3

InChIKey

QHUOBLDKFGCVCG-UHFFFAOYSA-N

SMILES

C(N(C)[Si](C)(C)C)(=O)C

CAS DataBase Reference

7449-74-3(CAS DataBase Reference)

NIST Chemistry Reference

Acetamide, n-methyl-n-(trimethylsilyl)-(7449-74-3)

EPA Substance Registry System

Acetamide, N-methyl-N-(trimethylsilyl)- (7449-74-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

37/39-16

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

F 

10-21

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29319090

MSDS

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

N-Methyl-N-(trimethylsilyl)acetamide Usage And Synthesis

Chemical Properties

clear light yellow liquid

Uses

N-Methyl-N-trimethylsilylacetamide may be used as a derivatizing reagent for the following:

• Quantification of the carbohydrate intermediates in glycation systems using gas chromatography coupled to mass spectrometry technique.
• Characterization of damaged products of thymine and cytosine formed by the exposure to UV light in a hydrogen peroxide solution using gas chromatography/mass spectrometry with scan mode and selected ion monitoring mode.

Reactions

The interaction of N-Methyl-N-(trimethylsilyl)acetamide with chloromethyl(methyl)-diacetoxysilane led to the formation of 2,4,6-trimethyl-2,4-bis((N-methylacetamido)methyl)-1,3,5,2,4-trioxadisilinan-6-ylium chloride[1].

General Description

N-Methyl-N-trimethylsilylacetamide is a trialkyl-silyl reagent and a versatile derivatizing agent used in gas chromatography (GC).

Purification Methods

N-Methyl-N-trimethylsilylacetamide [7449-74-3] M 145.3, b 48 -49o/11mm, 8 4o/13mm, 105-107o/35mm (solid at room temperature), d 4 0.90, n D 1.4379. A likely impurity is Et3N.HCl which can be detected by its odour. If it is completely soluble in *C6H6, then redistil; otherwise dissolve it in this solvent, filter and evaporate first in a vacuum at 12mm, then fractionate; all operations should be carried out in a dry N2 atmosphere. [Klebe et al. J Am Chem Soc 88 3390 1966, Ried & Suarez-Rivero Chem Ber 96 1473 1963, Beilstein 4 IV 4011.]

References

[1] Nataliya F. Lazareva, Igor M.Lazarev,lrina V.Sterkhova. "Trans-silylationof N-methyl-N-trimethylsilylacetamide with chloromethyl(methyl)diacetoxysilane."Journal of Organometallic Chemistry1006 (2023): Article 123000.

N-Methyl-N-(trimethylsilyl)acetamide(7449-74-3)Related Product Information

• Acetamide
• Methyl acrylate
• TRIMETHOXYCHLOROSILANEDISC 05/06/04
• N,N-Dimethylacetamide
• N-Methylacetamide
• Methylparaben
• Kresoxim-methyl
• Methanol
• Methyl salicylate
• N,O-Bis(trimethylsilyl)acetamide
• Trimethylsilylacetylene
• Acetaminophen
• METSULFURON METHYL
• Basic Violet 1
• Tribenuron methyl
• Lithium bis(trimethylsilyl)amide
• Methyl
• N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide