Tris(trimethylsilyl)methane

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. Reaction of tris(trimethylsilyl)methane with methyl lithium gives tris(trimethylsilyl)methyllithium, called trisyllithium. Trisyllithium is useful in Petersen olefination reactions:[1]

(tms)3CH + CH3Li → (tms)3CLi + CH4
(tms)3CLi + R2CO → (tms)2C=CR2 + tmsOLi
Tris(trimethylsilyl)methane
Names
Preferred IUPAC name
Methanetriyltris(trimethylsilane)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.154.179
  • 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).
Infobox references

Trisyllithium is also an effective precursor to bulky ligands. Some tris(trimethylsilyl)methyl derivatives are far more stable than less substituted derivatives. for example (Me3Si)3CTeH is a well-behaved tellurol.[2]

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

See also

References
  1. Sakurai, Hideki (2001). "Tris(trimethylsilyl)methane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt417.
  2. 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.
  3. Uhl, Werner; Graupner, Rene; Layh, Marcus; Schütz, Uwe (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.
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