Hexamethyldisilane

Introduction

Hexamethyldisilane (Me₃SiSiMe₃, CAS: 1450-14-2) is a hygroscopic colorless and odorless liquid which absorbs in the far UV region.[ ¹ ] In organic chemistry it is often used as an alternative of chlorotrimethylsilane or hexamethyldisilazane silylating agents. Hexamethyldisilane also promotes reduction and can act as a co-catalyst. It was recently revealed to be a key reagent in the anomerization of carbohydrates. Additionally, hexamethyldisilane can be a valuable starting material for the synthesis of sila-substituted organic and biologically active molecules. In the semiconductor industry this oligoorganosilane is employed as a precursor in the Chemical Vapor Deposition process.[ ² ] Hexamethyldisilane is commercially available, but it can be easily synthesized by reaction of chlorotrimethylsilane with an alkali metal in organic solvents (Scheme [1]).[ ³ ] This method is particularly efficient and cheap.[ ⁴ ]

Scheme 1  Efficient preparation of hexamethyldisilane in laboratory

• References

• 1 Semenov VV. Russ. Chem. Rev. 2011; 80: 313
• 2 Nordell N, Nishino S, Yang JW, Jacob C, Pirouz P. Appl. Phys. Lett. 1994; 64: 1647
• 3 Semenov VV, Egorov VA, Nerovnya AY, Domrachev GA. Dokl. Chem. (Engl. Transl.) 2005; 403: 141
• 4 Lickiss PD, Lucas R. J. Organomet. Chem. 1993; 444: 25
• 5 Blay G, Collado AM, García B, Pedro JR. Tetrahedron 2005; 61: 10853
• 6 Lee TW, Corey EJ. Org. Lett. 2001; 3: 3337
• 7 Tobisu M, Kita Y, Ano Y, Chatani N. J. Am. Chem. Soc. 2008; 130: 15982
• 8 Larsson JM, Zhao TS. N, Szabó KJ. Org. Lett. 2011; 13: 1888
• 9 Selander N, Paasch JR, Szabó KJ. J. Am. Chem. Soc. 2011; 133: 409
• 10 Shirakawa E, Otsuka H, Hayashi T. Chem. Commun. 2005; 5885
• 11 Otsuka H, Shirakawa E, Hayashi T. Chem. Commun. 2007; 1819
• 12 Kashiwabara T, Tanaka M. Tetrahedron Lett. 2005; 46: 7125
• 13 Kita Y, Tobisu M, Chatani N. Org. Lett. 2010; 12: 1864
• 14 Hwu JR, Tseng WN, Patel HV, Wong FF, Horng D.-N, Liaw BR, Lin LC. J. Org. Chem. 1999; 64: 2211
• 15 Malik S, Shah KJ, Kartha KP. R. Carbohydr. Res. 2010; 345: 867
• 16 Gluyas JB. G, Burschka C, Kraft P, Tacke R. Organometallics 2010; 29: 5897