N-Methyl-N-(trimethylsilyl)acetamide Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H314Causes severe skin burns and eye damage

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P501Dispose of contents/container to..…

N-Methyl-N-(trimethylsilyl)acetamide Chemical Properties,Usage,Production

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.