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Thermo Scientific™
N,O-Bis(trimethylsilyl)acetamide, 95%
CAS: 10416-59-8 | C8H21NOSi2 | 203.43 g/mol
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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
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規格表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.
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.
Solubility
Miscible with many nonpolar and polar aprotic solvents.
Notes
Air and moisture sensitive. Incompatible with strong oxidizing agents, water and acids.
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.
Solubility
Miscible with many nonpolar and polar aprotic solvents.
Notes
Air and moisture sensitive. Incompatible with strong oxidizing agents, water and acids.
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.