N,O-Bis(trimetilsilil)acetamida, 95 %, Thermo Scientific Chemicals

Name: N,O-Bis(trimetilsilil)acetamida, 95 %, Thermo Scientific Chemicals
SKU: L00183.14
Price: 43.80 EUR

CAS: 10416-59-8 | C8H21NOSi2 | 203.43 g/mol

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25 g

100 g

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Número de catálogo L00183.14

también denominado L00183-14

Precio (EUR)

43,80

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Cantidad:

25 g

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Precio (EUR)

43,80

Each

Identificadores químicos

CAS10416-59-8

IUPAC Nametrimethylsilyl N-(trimethylsilyl)ethanimidate

Molecular FormulaC8H21NOSi2

InChI KeySIOVKLKJSOKLIF-UHFFFAOYSA-N

SMILESCC(O[Si](C)(C)C)=N[Si](C)(C)C

Especificaciones Specification Sheet

Hoja de especificaciones

Appearance (Color)Clear, colorless to pale yellow

FormLiquid

Assay (GC)≥94.0%

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Aplicaciones
La N,O-bis(trimetilsilil)acetamida se utiliza como reactivo de desulfatación regioselectivo, y también como agente preparatorio para los éteres de carbohidratos y alcohol trimetilsililo. También se utiliza para la derivatización de grupos funcionales polares como ácidos carboxílicos, fenoles, esteroides, aminas, alcoholes, alcaloides y amidas. Se emplea en la formación de derivados estables de trimetilsililo. Además, se utiliza en química analítica para la derivatización de compuestos en análisis para aumentar su volatilidad e introducir el grupo de protección trimetilsililo en la síntesis orgánica. También se utiliza en la protección de grupos hidroxilos en productos naturales, grupos funcionales en productos intermediarios orgánicos y reactivos de derivatización para cromatografía de gases-análisis espectral de masas de ácidos fenólicos en frutas.

Solubilidad
Miscible con muchos disolventes apróticos no polares y polares.

Notas
Sensible al aire y a la humedad. Incompatible con agentes oxidantes fuertes agua y ácidos.

RUO – Research Use Only

General References:

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.