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

Identifiers
CAS Number	1068-69-5
3D model (JSmol)	Interactive image
ChemSpider	532318
ECHA InfoCard	100.154.179
PubChem CID	612377
CompTox Dashboard (EPA)	DTXSID50346465
InChI InChI=1S/C10H28Si3/c1-11(2,3)10(12(4,5)6)13(7,8)9/h10H,1-9H3 Key: BNZSPXKCIAAEJK-UHFFFAOYSA-N
SMILES C[Si](C)(C)C([Si](C)(C)C)[Si](C)(C)C
Properties
Chemical formula	C10H28Si3
Molar mass	232.589 g·mol^−1
Appearance	colorless liquid
Density	0.827 g/cm^3
Boiling point	219 °C (426 °F; 492 K)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, 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.

Structure of [InC(tms)₃]₄, an In(I) tetrahedrane (dark gray = In, orange = Si).[2]

See also

• Tris(trimethylsilyl)silane

References

1. Sakurai, Hideki (2001). "Tris(trimethylsilyl)methane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt417.
2. 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.