hexamethyldisilane

• ChemBase ID: 127685
• Molecular Formular: C6H18Si2
• Molecular Mass: 146.37812
• Monoisotopic Mass: 146.09470364
• SMILES: C[Si](C)(C)[Si](C)(C)C
• Canonical SMILES: C[Si]([Si](C)(C)C)(C)C
• InChI: InChI=1S/C6H18Si2/c1-7(2,3)8(4,5)6/h1-6H3
• InChIKey: NEXSMEBSBIABKL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: hexamethyldisilane
• IUPAC Traditional name: hexamethyldisilane
• Synonyms: Hexamethyldisilane; Hexamethyldisilane; 六甲基二硅烷

Database IDs

• CAS Number: 1450-14-2
• EC Number: 215-911-0
• MDL Number: MFCD00008258
• Beilstein Number: 1633463
• PubChem SID: 24852990; 162222003; 24874540
• PubChem CID: 74057
• Chemspider ID: 66675
• Wikipedia Title: Hexamethyldisilane

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.7566
• LogD (pH = 7.4): 2.7566
• Log P: 2.7566
• Molar Refractivity: 34.6806 cm^3
• Polarizability: 17.651302 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colourless liquid
• Melting Point: 12-13°C; 13.85°C (287K); 9-12 °C(lit.)
• Boiling Point: 112.85°C (386K); 112-113°C; 112-114 °C(lit.)
• Flash Point: -1°C(30°F); 11 °C; 51.8 °F
• Density: 0.715 g/mL at 25 °C(lit.); 0.721; 715 mg cm^-3
• Refractive Index: 1.422; 1.4220; n20/D 1.422(lit.); n20/D 1.423
• Std molar entropy: 255.89 J K^-1 mol^-1 (at 22.52 °C)

Safety Information

• RTECS: JM9170000
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1993; UN1993
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-36/37-43; R11, R36/37, R43
• Safety Statements: 16-23-45; 9-16-23-24-26-33-37; S16, S23, S45
• TSCA Listed: 是
• GHS Pictograms: GHS exclamation mark; GHS flame; GHS health hazard; GHS02; GHS07; GHS08
• GHS Signal Word: DANGER; Danger
• GHS Hazard statements: 225, 319, 334, 335; H225-H319-H317-H335; H225-H319-H334-H335
• GHS Precautionary statements: 210, 261, 305+351+338, 342+311; P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 2

Product Information

• Purity: ≥97.0% (GC); 98%; 98+%
• Grade: purum
• Linear Formula: (Si(CH3)3)2

DETAILS

Sigma Aldrich - 217069

Application
Silylating reagent for allylic acetates,1 aryl halides,2 and diketones.3 Source material for vapor deposition during silicon carbide growth.4
Source material for vapor deposition during silicon carbide growth.
Packaging
5, 10, 50 g in glass bottle

Sigma Aldrich - 52617

Other Notes
Starting material for a convenient preparation of trimethylsilyl alkali compounds1,2; For the generation of metal-free silyl anion with TASF3

REFERENCES

• Precursor of TMSLi, TMSNa and TMSK by cleavage with alkyllithiums or alkoxides. Reaction of the metallated derivatives with aryl halides gives aryltrimethylsilanes: J. Org. Chem., 42, 2654 (1977). The anion adds 1,4-to ɑ?-enones to give ?-silyl ketones: J. Org. Chem., 41, 3063 (1976); Tetrahedron Lett., 24, 3497 (1983). The anion may also be used to deoxygenate secondary nitroalkanes (to ketoximes), nitrones (to imines), and heterocyclic N-oxides: J. Org. Chem., 64, 2211 (1999).
• Also cleaved by TBAF to give the "salt-free" silyl anion, which adds to aldehydes to give, after acid hydrolysis, ɑ-hydroxy silanes: J. Org. Chem., 48, 912 (1983). TBAF also catalyzes the silylation of OH groups under very mild conditions: Tetrahedron Lett., 35, 8413 (1994). See Appendix 4.
• Couples with aryl, benzyl or allyl halides in the presence of Tetrakis(triphenylphosphine)palladium(0), 10548, to give the corresponding silanes: J. Organomet. Chem., 148, 97 (1978); 225, 331 (1982).
• Aryl and alkenyl nitriles undergo ipso-silylation-decyanation, catalyzed by Chloro(1,5-cyclooctadiene)rhodium(I) dimer, 10466, to give the corresponding trimethylsiliyl derivatives: J. Am. Chem. Soc., 128, 8152 (2006).