Tris(trimethylsilyl)methane

Tris(trimethylsilyl)methane
Names
Preferred IUPAC name
Methanetriyltris(trimethylsilane)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.154.179 Edit this at Wikidata
  • InChI=1S/C10H28Si3/c1-11(2,3)10(12(4,5)6)13(7,8)9/h10H,1-9H3
    Key: BNZSPXKCIAAEJK-UHFFFAOYSA-N
  • C[Si](C)(C)C([Si](C)(C)C)[Si](C)(C)C
Properties
C10H28Si3
Molar mass 232.589 g·mol−1
Appearance colorless liquid
Density 0.827 g/cm3
Boiling point 219 °C (426 °F; 492 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tris(trimethylsilyl)methane is the organosilicon compound with the formula (tms)3CH (where tms = (CH3)3Si). It is a colorless liquid that is highly soluble in hydrocarbon solvents.

Trisyl chemistry

Structure of [InC(tms)3]4, an In(I) tetrahedrane (dark gray = In, orange = Si).[1]

Reaction of tris(trimethylsilyl)methane with methyl lithium gives tris(trimethylsilyl)methyllithium, called trisyllithium:

(tms)3CH + CH3Li → (tms)3CLi + CH4

Trisyllithium is useful in Petersen olefination reactions:[2]

(tms)3CLi + R2CO → (tms)2C=CR2 + tmsOLi

Trisyllithium is also a source of the bulky trisyl ligand. Some tris(trimethylsilyl)methyl derivatives are far more stable than less substituted derivatives. For example, (Me3Si)3CTeH is a well-behaved tellurol.[3] [(Me3Si)3CTl]4 is a rare example of a robust organothallium(I) compound.[4]

See also

References

  1. ^ Uhl W, Graupner R, Layh M, Schütz U (1995). "In4{C(SiMe3)3}4 mit In4-tetraeder und In4Se4{C(SiMe3)3}4 mit In4Se4- heterocubanstruktur". Journal of Organometallic Chemistry. 493 (1–2): C1 – C5. doi:10.1016/0022-328X(95)05399-A.
  2. ^ Sakurai H (2001). "Tris(trimethylsilyl)methane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt417. ISBN 0-471-93623-5.
  3. ^ Sadekov ID, Zakharov AV (1999). "Stable tellurols and their metal derivatives". Russ. Chem. Rev. 68 (11): 909–923. Bibcode:1999RuCRv..68..909S. doi:10.1070/rc1999v068n11abeh000544. S2CID 250864006.
  4. ^ Uhl W, Keimling SU, Klinkhammer KW, Schwarz W (1997). "TlI[C(SiMe3)3]—An Alkylthallium(I) Compound with a Distorted Tetrahedron of Tl Atoms in the Solid State". Angewandte Chemie International Edition in English. 36 (1–2): 64–65. doi:10.1002/anie.199700641.

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