Synlett 2011(5): 732-733  
DOI: 10.1055/s-0030-1259594
© Georg Thieme Verlag Stuttgart ˙ New York

Lithium Bis(trimethylsilyl)amide

Yong-Hui Liu*
The College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050016, P. R. of China
Further Information

Publication History

Publication Date:
25 February 2011 (online)


Lithium bis(trimethylsilyl)amide (LiHMDS) is a colorless solid, which is soluble in a variety of organic solvents suitable for reactive compounds, such as organometallic substances or substituted metal amides. The compound melts at 71-72 ˚C. [¹] It is unstable in air and catches fire when compressed, but it is stable in an atmosphere of nitrogen. Reactions with a variety of nonmetallic halides give lithium halides and hexamethyldisilazyl derivatives. The preparation of lithium bis(trimethylsilyl)amid must be performed in an atmosphere of dry nitrogen. The pentane containing n-butyllithium is added slowly to a stirred solution of hexamethyldisilazane (Scheme [¹] ). The reaction mixture is boiled for 30 minutes, and evaporate the solvents. LiHMDS is obtained as colorless crystals.

Scheme 1


  • 1 Amonoo-Neizer EH. Shaw RA. Skovlin DO. Smith BC. Inorg. Synth.  1966,  8:  19 
  • 2 Li B. Pai R. Cardinale SC. Butler MM. Peet NP. Moir DT. Bavari S. Bowlin TL. J. Med. Chem.  2010,  53:  2264 
  • 3 Baird B. Pawlikowski AV. Su J. Wiench JW. Pruski M. Sadow AD. Inorg. Chem.  2008,  47:  10208 
  • 4 Petersen MÅ. Broman SL. Kadziola A. Kilså K. Nielsen MB. Eur. J. Org. Chem.  2009,  2733 
  • 5 Wehn PM. Harrington PE. Eksterowicz JE. Org. Lett.  2009,  11:  5666 
  • 6 Pragani R. Stallforth P. Seeberger PH. Org. Lett.  2010,  12:  1624 
  • 7 Ruediger E. Martel A. Meanwell N. Solomon C. Turmel B. Tetrahedron Lett.  2004,  45:  739 
  • 8 Lee C. Lee JM. Lee NR. Kima DE. Jeong YJ. Chong Y. Bioorg. Med. Chem. Lett.  2009,  19:  4538 
  • 9 Tanaka S. Kochi K. Ito H. Mukawa J. Kishikawa K. Yamamoto M. Kohmoto S. Synth. Commun.  2009,  39:  868 
  • 10 Urgaonkar S. Verkade JG. Adv. Synth. Catal.  2004,  346:  611 
  • 11 McBee JL. Escalada J. Tilley TD. J. Am. Chem. Soc.  2009,  131:  12703