Tris(trimethylsilyl)methane

Tris(trimethylsilyl)methane
Names
	Preferred IUPAC name Methanetriyltris(trimethylsilane)
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/cm3
Boiling point	219 °C (426 °F; 492 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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

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]

References

^ Uhl W, Graupner R, Layh M, Schütz U (1995). "In4{C(SiMe₃)₃}₄ mit In₄-tetraeder und In₄Se₄{C(SiMe₃)₃}₄ mit In₄Se_4- heterocubanstruktur". Journal of Organometallic Chemistry. 493 (1–2): C1–C5. doi:10.1016/0022-328X(95)05399-A.
^ Sakurai H (2001). "Tris(trimethylsilyl)methane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt417. ISBN 0-471-93623-5.
^ 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.
^ Uhl W, Keimling SU, Klinkhammer KW, Schwarz W (1997). "Tl^I[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.

[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 In₄Se_4- 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.

[Stable-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). "Tl^I[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.

[1]

[2]

[3]

[4]

Tris(trimethylsilyl)methane

Trisyl chemistry

See also

References