bis(dimethylsilyl)amine

• ChemBase ID: 112754
• Molecular Formular: C4H15NSi2
• Molecular Mass: 133.3396
• Monoisotopic Mass: 133.07430255
• SMILES: C[SiH](C)N[SiH](C)C
• Canonical SMILES: C[SiH](N[SiH](C)C)C
• InChI: InChI=1S/C4H15NSi2/c1-6(2)5-7(3)4/h5-7H,1-4H3
• InChIKey: NQCZAYQXPJEPDS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(dimethylsilyl)amine
• IUPAC Traditional name: bis(dimethylsilyl)amine
• Synonyms: TETRAMETHYL DISILAZANE; TMDS; 1,1,3,3-Tetramethyldisilazane; Bis(dimethylsilyl)amine; Tetramethyldisilazane; 1,1,3,3-四甲基二硅氮烷; 四甲基二硅氮烷

Database IDs

• CAS Number: 15933-59-2
• EC Number: 240-072-2
• MDL Number: MFCD00025626
• Beilstein Number: 741869
• PubChem SID: 162097892; 24848399
• PubChem CID: 6327317

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -4.1027784
• LogD (pH = 7.4): -3.7365577
• Log P: -0.5031
• Molar Refractivity: 38.6353 cm^3
• Polarizability: 15.48848 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 99-100 °C
• Boiling Point: 99-100°C
• Flash Point: 26.6 °F; -3 °C; -3°C(26°F)
• Density: 0.752 g/mL at 25 °C(lit.); 0.768
• Refractive Index: 1.4055; n20/D 1.404(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); Irritant (Xi)
• UN Number: 2924; UN2924
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-34; 11-36/37/38
• Safety Statements: 16-26-36; 16-26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H314-H318; H225-H315-H319-H335
• GHS Precautionary statements: P210-P261-P305 + P351 + P338; P210-P280-P303+P361+P353-P305+P351+P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2924 3/PG 2

Product Information

• Purity: ≥97.0% (GC); 95+%; 97%; 98+%
• Grade: purum
• Linear Formula: [(CH3)2SiH]2NH

DETAILS

MP Biomedicals - 05225649

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 139246

Packaging
10 g in glass bottle

Sigma Aldrich - 87830

Other Notes
Silylating agent1; Silylation/hydrosilylation of β-hydroxy alkenes to silolanes2,3

REFERENCES

• Reagent for the preparation (see Appendix 4) of dimethylsilyl (DMS) derivatives, compare Hexamethyldisilazane, A15139. With allylic and homoallylic alcohols, the products can undergo Pt- or Rh-catalyzed intramolecular hydrosilylation, providing a regioselective route to 1,3-diols: J. Am. Chem. Soc., 108, 6090 (1986). For an example of this reaction, see Chlorodimethylsilane, A13113.
• The potassium derivative, formed by reaction with KH in THF, reacts with alkyl halides to give, after hydrolysis, high yields of primary amines, thus providing a convenient alternative to the classical Gabriel method. Other silazanes, including hexamethyldisilazane, give lower yields: Synthesis, 150 (1995):