7449-74-3

Basic information

• Product Name: N-Methyl-N-(trimethylsilyl)acetamide
• Synonyms: N-Methyl-N-TMS-acetamide;N-Methyl-N-trimethylsilylacetamide [Trimethylsilylating Agent];N-Methyl-N-trimethylsilylacetamine;N-Methyl-N-(trimethylsilyl)acetamide,98%;[TriMethylsilylating Agent];N-Methyl-N-triMethylsilylacetaMide N-METHYL-N-TRIMETHYLSILYACETAMIDE;N-METHYL-N-TRIMETHYLSILYLACETAMIDE
• CAS NO: 7449-74-3
• Molecular Formula: C₆H₁₅NOSi
• Molecular Weight: 145.27
• EINECS: 231-217-0
• Product Categories: Analytical Chemistry;GC Derivatizing Reagents;Si (Classes of Silicon Compounds);Silylacetamides;Silylation (GC Derivatizing Reagents);Si-N Compounds;Trimethylsilylation (GC Derivatizing Reagents)
• Mol File: 7449-74-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 159-161 °C(lit.)
• Flash Point: 48 °C
• Appearance: Clear light yellow/lyophilized powder
• Density: 0.904 g/mL at 20 °C(lit.)
• Vapor Pressure: 6.41mmHg at 25°C
• Refractive Index: n20/D 1.439
• Storage Temp.: 2-8°C
• PKA: -0.11±0.70(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 506975
• CAS DataBase Reference: N-Methyl-N-(trimethylsilyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-N-(trimethylsilyl)acetamide(7449-74-3)
• EPA Substance Registry System: N-Methyl-N-(trimethylsilyl)acetamide(7449-74-3)

Safety Data

• Hazard Codes: Xi
• 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
• Hazardous Substances Data: 7449-74-3(Hazardous Substances Data)

Usage

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.

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.]

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

Upstream product

• 63877-23-6 (trimethylsilyl)acetyl chloride 
• 53998-37-1 Trimethylsilyl-essigsaeure-N-acetyl-N-methyl-amid 
• 4071-85-6 trimetylsilylketene 
• 79-16-3 N-methyl-acetamide 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 23138-68-3 N-methyltrimethylsilylacetamide 
• 23184-22-7 N-Methyl-N-<1-(trimethylsiloxy)vinyl>acetamid 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 7331-84-2 N,N-Bis(trimethylsilyl)propylamin 
• 66408-01-3 C₁₁H₁₇BN₂O 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 38806-26-7 N-ethyl-N-methylacetamide 
• 17882-06-3 trimethylsilyl benzenesulfonate 
• 75-77-4 chloro-trimethyl-silane 
• 67519-73-7 N-[chloro(dimethyl)silylmethyl]-N-(methyl)acetamide 
• 37010-19-8 4,4'-?dithiobis(2,1-phenylenecarbonylimino)bisbenzoic acid 
• 96835-64-2 (4-{2-[2-(4-Carboxymethyl-phenylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-phenyl)-acetic acid 
• 205499-82-7 1,1'-[dithiobis(2,1-phenylenecarbonyl)]bis-4-piperidine carboxylic acid 
• 177786-37-7 2,2'-dithiobis(2,1-phenylenecarbonylimino)bisbenzoic acid 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 39158-85-5 2-methyl-1-phenyl-1-trimethylsiloxy-1-propene 
• 53282-55-6 (trimethylsiloxymethylidene)cyclohexane 

Relevant articles and documents

INDUSTRIAL PROCESS FOR THE PREPARATION OF N-ALKYL-N-TRIALKYLSILYLAMIDES

The present invention relates to a process for producing N-alkyl-N- trialkylsilylamides from trialkylsilylhalides and N-alkylamides in the presence of a base and in the absence of a solvent.

Multiple Reaction Channels of (N-Acyl-N-alkylcarbamoyl)oxyl Radicals from N-Acyl PTOC Carbamates

N-Acyl-N-alkyl-N'-hydroxypyridine-2-thione carbamates (N-acyl PTOC carbamates) 1 are prepared in good to excellent yield by reactions of N-acylcarbamoyl chlorides with N-hydroxypyridine-2-thione sodium salt.Methods for production of the requisite carbamoyl chlorides by reaction of a secondary amide with trimethylsilyl triflate followed by treatment with phosgene were optimized.Precursors 1 react in radical chain reactions to give the title radicals (2) that can further react by several pathways.Decarboxylations of radicals 2 give amidyl radicals, and this method is excellent for production of acetamidyl radicals and in particular the N-methylacetamidyl radical which is difficult to prepare by other routes. 5-Exo cyclizations of amidyl radicals produced by decarboxylation of 2 give, ultimately, lactams and N-acylpyrrolidines. 1,5-Hydrogen transfer reactions of 2 to give α-amide radicals compete with decarboxylation; cyclization of an α-amide radical thus formed also is reported.The Lewis acid MgBr2 can reduce the 1,5-hydrogen atom transfer reaction apparently by a chelation effect on the precursor that leads to production of radical 2 in a conformation unfavorable for hydrogen atom transfer.By appropriate experimental design, radicals 2 often can be directed toward one desired reaction, and several relative rate constants for reactions of 2 necessary for such design were determined in this work.

N'-ACYL-N-ALKYLCARBAMOYLOXY RADICALS: ENTRIES TO AMIDYL RADICALS BY DECARBOXYLATION AND TO α-AMIDE RADICALS BY RADICAL TRANSLOCATION

N'-Acyl-N-hydroxypyridine-2-thione carbamates react in radical chain reactions to give the title radicals which can decarboxylate or react by intramolecular hydrogen atom transfer; the competing reaction pathways are controlled by the structure of the alkyl group and the conformation of the precursor which can be influenced by addition of a Lewis acid.