Hexamethyldisilane

Hexamethyldisilane (TMS₂) is the organosilicon compound with the formula Si₂(CH₃)₆, abbreviated Si₂Me₆. It is a colourless liquid, soluble in organic solvents.[1]

Hexamethyldisilane

Ball-and-stick model Space-filling model
Identifiers
CAS Number	1450-14-2
3D model (JSmol)	Interactive image
Beilstein Reference	1633463
ChemSpider	66675
ECHA InfoCard	100.014.465
EC Number	215-911-0
PubChem CID	74057
RTECS number	JM9170000
UN number	1993
CompTox Dashboard (EPA)	DTXSID2061698
InChI InChI=1S/C6H18Si2/c1-7(2,3)8(4,5)6/h1-6H3 Key: NEXSMEBSBIABKL-UHFFFAOYSA-N
SMILES C[Si](C)(C)[Si](C)(C)C
Properties
Chemical formula	Si2C6H18
Molar mass	146.39 g mol^−1
Appearance	Colourless liquid
Density	0.715 g/cm^3
Melting point	14 °C; 57 °F; 287 K
Boiling point	113 °C; 235 °F; 386 K
Refractive index (nD)	1.422
Thermochemistry
Std molar entropy (S^o298)	255.89 J K^−1 mol^−1 (at 22.52 °C)
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H319, H334, H335
GHS precautionary statements	P210, P261, P305+351+338, P342+311
Flash point	11 °C (52 °F; 284 K)
Related compounds
Related alkylsilanes	Tetramethylsilane Triethylsilane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The Si-Si bond in hexamethyldisilane is cleaved by strong nucleophiles and electrophiles. Alkyl lithium compounds react as follows:

Si₂Me₆ + RLi → RSiMe₃ + LiSiMe₃

Iodine gives trimethylsilyl iodide.[2]

Me₃Si−SiMe₃ + I₂ → 2 SiMe₃I

References

1. Tamejiro Hiyama, Manabu Kuroboshi, "Hexamethyldisilane" Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons. doi:10.1002/047084289X.rh015
2. Olah, G.; Narang, S.C. (1982). "Iodotrimethylsilane—a versatile synthetic reagent". Tetrahedron. 38 (15): 2225. doi:10.1016/0040-4020(82)87002-6.