diethyl(trimethylsilyl)amine

• ChemBase ID: 104757
• Molecular Formular: C7H19NSi
• Molecular Mass: 145.31796
• Monoisotopic Mass: 145.12867615
• SMILES: CCN(CC)[Si](C)(C)C
• Canonical SMILES: CCN([Si](C)(C)C)CC
• InChI: InChI=1S/C7H19NSi/c1-6-8(7-2)9(3,4)5/h6-7H2,1-5H3
• InChIKey: JOOMLFKONHCLCJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl(trimethylsilyl)amine
• IUPAC Traditional name: diethyl(trimethylsilyl)amine
• Synonyms: N-(Trimethylsilyl)diethylamine; N-TRIMETHYLSILYL DIETHYLAMINE; TMSDEA; (Diethylamino)trimethylsilane; N-(Trimethylsilyl)diethylamine; N,N-Diethyltrimethylsilylamine; N,N-Diethyl-1,1,1-trimethylsilylamine; N-TRIMETHYLSILYLDIETHYLAMINE; N-(三甲基硅基)二乙胺; (二乙氨基)三甲基硅烷; N-(三甲基甲硅烷基)二乙胺; N,N-二乙基三甲基甲硅烷胺

Database IDs

• CAS Number: 996-50-9
• EC Number: 213-637-6
• MDL Number: MFCD00009040
• Beilstein Number: 635718
• PubChem SID: 162091987; 24864626; 24859530; 24847772
• PubChem CID: 70454

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -1.4219337
• LogD (pH = 7.4): -1.3960248
• Log P: 1.8515
• Molar Refractivity: 40.7309 cm^3
• Polarizability: 18.099138 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -10°C
• Boiling Point: 125-126 °C(lit.); 125-126°C
• Flash Point: 10°C(50°F); 48.2 °F; 9 °C
• Density: 0.760; 0.767 g/mL at 25 °C(lit.); 0.77 g/ml
• Refractive Index: 1.4110; n20/D 1.411(lit.); n20/D 1.412
• Vapor Density: >1 (vs air)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: 2733; UN2733
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-34; R:34
• Safety Statements: 16-26-36/37/39-45; 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H314; H225-H314-H318
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2733 3/PG 2

Product Information

• Purity: ≥95.0% (GC); 95%; 97%; 98%
• Grade: derivatization grade; purum; Selectophore™
• Linear Formula: (C2H5)2NSi(CH3)3

DETAILS

MP Biomedicals - 05223114

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02157087

(N,N-Diethyl-1,1,1-trimethylsilylamine)
Purity: 95%
1 ml = approx. 0.77 g

Sigma Aldrich - 394890

Packaging
5 mL in glass bottle

Sigma Aldrich - 127256

Packaging
25, 100 g in glass bottle

Sigma Aldrich - 32575

Other Notes
Silylating agent1,2

Sigma Aldrich - 32574

General description
Visit our Sensor Applications portal to learn more.
Legal Information
Selectophore is a trademark of Sigma-Aldrich GmbH

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.