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10416-59-8 - N,O-Bis(trimethylsilyl)acetamide, 95% - BSA - L00183 - Alfa Aesar

L00183 N,O-Bis(trimethylsilyl)acetamide, 95%

Codice CAS
10416-59-8
Sinonimi
BSA

Dimensioni Prezzo ($) Quantità Disponibilità
25g 33,10
100g 85,60
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N,O-Bis(trimethylsilyl)acetamide, 95%

MDL
MFCD00008270
EINECS
233-892-7

Proprietà chimiche

Formula
C8H21NOSi2
Peso formula
203.43
Punto di fusione
-24°
Punto di ebollizione
71-73°/35mm
Punto di infiammabilità
42°(107°F)
Densità
0.829
Indice di rifrazione
1.4170
Sensibilità
Moisture Sensitive
Solubilità
Miscible with many nonpolar and polar aprotic solvents.

Applicazioni

N,O-Bis(trimethylsilyl)acetamide is used as a regioselective desulfation reagent as well as a preparatory agent for carbohydrate and alcohol trimethylsilyl ethers. It is also used for the derivatization of polar functional groups such as carboxylic acids, phenols, steroids, amines, alcohols, alkaloids and amides. It is employed in the formation of stable trimethylsilyl derivatives. Further, it is used in analytical chemistry for the derivatization of compounds in analysis to increase their volatility and to introduce the trimethylsilyl protecting group in organic synthesis. In addition to this, it is used in the protection of hydroxyl groups in natural products, functional groups in organic intermediates and derivatization reagent for gas chromatography-Mass spectral analysis of phenolic acids in fruits.

Note

Air and moisture sensitive. Incompatible with strong oxidizing agents, water and acids.

Letteratura

Powerful silylation reagent for a wide range of functional groups under mild conditions. See Appendix 4. Reviews: J. Prakt. Chem./ Chem. Ztg., 337, 332 (1995); Synthesis, 357 (1998). Unlike halosilanes, silylated amides often need no added base catalysts. For an example of use without added solvent or catalyst for the silylation of a tertiary ɑ-hydroxy ketone, see: Org. Synth. Coll., 7, 381 (1990). Silylating power can be increased in polar solvents such as DMF or acetonitrile, or by addition of acidic catalysts, often TMS chloride, or an acid such as TFA or HCl.

O-Silylation in the presence of TBAF (0.02 equiv.) occurs under very mild conditions: Tetrahedron Lett., 35, 8409 (1994).

BSA catalyzes the acylation of acylphosphoranes with activated derivatives of carboxylic acids. Subsequent ozonolysis, or oxidation with singlet oxygen or dimethyldioxirane, provides a route to 1,2,3-triketones: J. Org. Chem., 54, 2785 (1989); 60, 8231 (1995):

Saraji, M.; Ghambari, H. Suitability of dispersive liquid-liquid microextraction for the in situ silylation of chlorophenols in water samples before gas chromatography with mass spectrometry. J. Sep. Sci. 2015, 38 (20), 3552-3559.

Wittel, G.; Gu, P.; Engels, J. W. Synthesis and activity of C-analogues for immune stimulating CpG-oligodeoxynucleotides. Collect. Czech. Chem. Commun. 2015, 7, 493-494.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H226-H302-H314-H318

Flammable liquid and vapour. Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.

Dichiarazioni precauzionali: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
1306669
Classe di rischio
8
Gruppo di imballaggio
II
Codice tariffe armonizzato
2931.90
TSCA
Yes
RTECS
AK3000000

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