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996-50-9 - N-(Trimethylsilyl)diethylamine, 98% - (Diethylamino)trimethylsilane - TMSDEA - A18149 - Alfa Aesar

A18149 N-(Trimethylsilyl)diethylamine, 98%

CAS Number
996-50-9
Synonyms
(Diethylamino)trimethylsilane
TMSDEA

Size Price ($) Quantity Availability
25g 44.50
100g 135.00
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N-(Trimethylsilyl)diethylamine, 98%

MDL
MFCD00009040
EINECS
213-637-6

Chemical Properties

Formula
(CH3)3SiN(CH2CH3)2
Formula Weight
145.32
Melting point
-10°
Boiling Point
125-126°
Flash Point
10°(50°F)
Density
0.760
Refractive Index
1.4110
Sensitivity
Moisture Sensitive
Solubility
Hydrolyzes in water.

Applications

It is used to derivative polar organic compounds. N,N-Diethyl(trimethylsilyl)amine is a chemical reagent with wide application in organic chemistry and used in stereo specific addition reactions as well as in SN2 nucleophilic substitutions.

Notes

Moisture Sensitive. Store away from oxidizing agents, water/moisture. Store under inert gas. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Literature References

Said Kinani.; Stéphane Bouchonnet.; Sophie Bourcier.; Jean-Marc Porcher.; Sélim Aït-Aïssa.Study of the chemical derivatization of zearalenone and its metabolites for gas chromatography-mass spectrometry analysis of environmental samples.J Chromatogr A.2008,1190(1), 307-315.

Yasushi Yamamoto.; Hideaki Shimizu.; Chinami Matui.; & Michiru Chind. Transformation of Oxiranes to β-Trimethylsilyloxyalkyl Iodide by N-(Trimethylsilyl) diethylamine and Methyl Iodide.Main Group Chem.1996,1(4), 409-414.

Moderately powerful silylating agent which functions as its own base (see Appendix 4). In the silylation of alcohols, the reagent is sensitive to steric effects. Thus, the equatorial hydroxyl group of 3-ß-tropanol can be silylated selectively: Acta Chim. Acad. Sci. Hung., 58, 189 (1968); J. Am. Chem. Soc., 96, 5876 (1974).

In the presence of MeI, primary amines such as aniline are converted to their N,N-bis(trimethylsilyl) derivatives: J. Organomet. Chem., 510, 1 (1996), and ketones to silyl enol ethers in high yield: Organometallics, 16, 2204 (1997). The combination with an alkyl iodide or bromide also provides a convenient method for generating the iodo- or bromotrialkylsilane equivalent in ring-opening of cyclic ethers. With 1 mol of reagent the main product is the ω-siloxy alkyl halide; excess reagent affords the terminal dihalide: J. Org. Chem., 64, 8024 (1999).

Promotes direct 1,4-addition of ɑ-unsubstituted aldehydes to electron deficient olefins, specifically with enones to give δ-keto aldehydes: J. Chem. Soc., Perkin 1, 316 (2001). Alternative conditions were found to be ineffective.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H314-H318

Highly flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. 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.

Other References

Beilstein
635718
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
Yes

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