N-(Trimethylsilyl)diethylamine

• Catalog No.: A18149
• CAS Number: 996-50-9
• M. F.: C7H19NSi
• M. W.: 145.31796
• Purity: 98%

SYNONYMS

• Title: N-(三甲基硅基)二乙胺
• IUPAC name: diethyl(trimethylsilyl)amine
• IUPAC Traditional name: diethyl(trimethylsilyl)amine
• Synonyms: TMSDEA; (Diethylamino)trimethylsilane

DATABASE IDS

• EC Number: 213-637-6
• MDL Number: MFCD00009040
• Beilstein Number: 635718
• CAS Number: 996-50-9

PROPERTIES

• Purity: 98%
• Boiling Point: 125-126°C
• Density: 0.760
• Flash Point: 10°C(50°F)
• Melting Point: -10°C
• Refractive Index: 1.4110
• GHS Hazard statements: H225-H314-H318
• European Hazard Symbols: Corrosive (C)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 11-34
• Safety Statements: 16-26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN2733
• Packing Group: II

REFERENCES

• 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-?-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.