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

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

Numéro CAS
10416-59-8
Synonymes
BSA

Dimensions Prix ($) Quantité Disponibilité
5g 16,56
25g 28,80
100g 76,59
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N,O-Bis(trimethylsilyl)acetamide, 95%

MDL
MFCD00008270
EINECS
233-892-7

Propriétés chimiques

Formule
C8H21NOSi2
Poids formulaire
203.43
Point de fusion
-24°
Point d'ébullition
71-73°/35mm
Point d'éclair
42°(107°F)
Densité
0.829
Indice de réfraction
1.4170
Sensibilité
Moisture Sensitive
Solubilité
Miscible with many nonpolar and polar aprotic solvents.

Applications

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.

Notes

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

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H314-H318-H226-H302

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

Mentions de prudence: P210-P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. 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. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
1306669
Classe de danger
8
Groupe d'emballage
II
Code tarifaire harmonisé
2931.90
TSCA
Yes
RTECS
AK3000000

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