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N-Trimethylsilylacetamide

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Identification
Molecular formula
C5H13NOSi
CAS number
10416-59-8
IUPAC name
N-trimethylsilylacetamide
State
State

N-Trimethylsilylacetamide is a liquid at room temperature.

Melting point (Celsius)
-55.30
Melting point (Kelvin)
217.85
Boiling point (Celsius)
82.00
Boiling point (Kelvin)
355.15
General information
Molecular weight
131.26g/mol
Molar mass
131.2630g/mol
Density
0.8059g/cm3
Appearence

N-Trimethylsilylacetamide is a colorless liquid. It is often described as practically odorless.

Comment on solubility

Solubility of N-trimethylsilylacetamide

N-trimethylsilylacetamide (TMSA) is an interesting chemical compound with distinct solubility properties. Its solubility can be explained through various factors:

  • Polarity: TMSA contains a polar amide functional group, which can interact favorably with polar solvents.
  • Solvent Compatibility: It is generally soluble in common organic solvents such as acetone, ethyl acetate, and chloroform, making it versatile for various applications.
  • Water Solubility: Unlike many amides, TMSA has limited solubility in water due to its bulky trimethylsilyl group, which decreases the overall polarity of the molecule.

As a result, TMSA is often utilized in organic reactions as a silylating agent or protective group. In summary, while its solubility profile is strong in non-polar to mildly polar solvents, it does not extend significantly to highly polar solvents like water. As one wise adage goes, "like dissolves like," and this holds true for N-trimethylsilylacetamide.

Interesting facts

Interesting Facts about N-trimethylsilylacetamide

N-trimethylsilylacetamide (TMS-acetamide) is a fascinating chemical compound that plays a significant role in both synthetic and analytical chemistry. Here are some intriguing insights about this versatile compound:

  • Functional Role: TMS-acetamide is widely used as a derivatizing agent, particularly in gas chromatography-mass spectrometry (GC-MS) analyses. It enhances the volatility and thermal stability of polar compounds, making them easier to analyze.
  • Synthetic Applications: As a reactant, TMS-acetamide serves as a source of the trimethylsilyl group, which can protect functional groups during multi-step synthesis, a crucial step in organic synthesis routes.
  • Reaction Mechanisms: The silylation reaction mechanisms involving TMS-acetamide can aid in understanding how compounds interact with each other at a molecular level. This knowledge is vital for both theoretical and practical chemistry and can provide insights into reaction pathways.
  • Environmental Analysis: In the field of environmental science, TMS-acetamide can be used to analyze residues of organophosphorus pesticides, showcasing its importance beyond traditional synthetic applications.
  • Precision and Efficiency: The use of TMS-acetamide in creating stable derivatives often leads to increased precision in quantification and identification during analytical procedures, highlighting its value to chemists and researchers.
  • Emerging Technologies: With the rise of mass spectrometry techniques, TMS-acetamide’s relevance continues to grow, prompting ongoing studies into its properties and uses in emerging fields such as metabolomics and proteomics.

With its unique chemical structure and diverse applications, N-trimethylsilylacetamide remains a compound of interest for scientists and students alike. Its ability to enhance the study of complex mixtures gives it a prominent place in modern analytical practices.

Synonyms
N-(Trimethylsilyl)acetamide
13435-12-6
N-Trimethylsilylacetamide
ACETAMIDE, N-(TRIMETHYLSILYL)-
Trimethylsilylacetamide
(Acetylamino)trimethylsilane
EINECS 236-565-7
NSC 139859
BRN 0741928
DTXSID8065454
4-04-00-04011 (Beilstein Handbook Reference)
DTXCID2034205
236-565-7
C5H13NOSi
Acetamide, TMS derivative
n-trimethylsilyl-acetamide
MFCD00008671
TMS acetamide
N-TMS-acetamide
(Acetylamino)trimethylsilane; N-(Trimethylsilyl)acetamide; NSC 139859; Trimethylsilylacetamide; TMS-acetamide; TMS acetamide
N-trimethylsilylacetoamide
n-(trimethylsilyl)-acetamide
SCHEMBL321022
N-mono(trimethylsilyl)acetamide
SCHEMBL8835944
SCHEMBL10541857
SCHEMBL10541860
N-(Trimethylsilyl)acetamide, 95%
WLN: 1VM-SI-1&1&1
CT3250
NSC139859
AKOS015837704
FS-5493
NSC-139859
DB-371193
CS-0187550
NS00054346
T0590
D92366
EN300-109884
S18875
N-(Trimethylsilyl)acetamide, for GC derivatization, >=98.0% (GC)