Synlett 2010(5): 837-838  
DOI: 10.1055/s-0029-1219345
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Trimethylsilyl Chloride (TMSCl)

Yanchun Li*
College of Chemistry and Chemical Engineering, Northwest Normal University, 730070 Lanzhou, P. R. of China
e-Mail: lychun123@126.com.cn;
Further Information

Publication History

Publication Date:
24 February 2010 (online)

Introduction

Trimethylsilyl chloride is a valuable reagent in organic synthesis. It is a colorless liquid with a boiling point of 57-58 ˚C, easy to hydrolyse, unstable towards air, and has a pungent odor. It is commercially available and has been widely used in organic synthesis as chloridizing and activating reagents. Further it is used as protecting group and to accelerate and improve yields, stereospecificity, and regioselectivity for organic reactions. Herein, the applications of TMSCl in the recent five years are listed and reviewed.

    References

  • 1 Lee PH. Seomoon D. Lee K. Heo Y. J. Org. Chem.  2003,  68:  2510 
  • 2 Prakash GKS. Panja C. Mathew T. Surampudi V. Petasis NA. Olah GA. Org. Lett.  2004,  6:  2205 
  • 3 Ryabukhin SV. Plaskon AS. Volochnyuk DM. Shivanyuk AN. Tolmachev AA. J. Org. Chem.  2007,  72:  7417 
  • 4 Liu Y. Zhao Q. Zhang Y. Tetrahedron Lett.  2004,  45:  4571 
  • 5 Prakash GKS. Mathew T. Panja C. Olah GA. J. Org. Chem.  2007,  72:  5847 
  • 6 Wan JP. Zhou J. Mao H. Pan YJ. Wu AX. Tetrahedron  2008,  64:  11115 
  • 7 Mao H. Wan J. Pan Y. Tetrahedron  2009,  65:  1026 
  • 8 Li Y. Goeke A. Wang R. Wang Q. Frater G. Tetrahedron  2007,  63:  9605 
  • 9 Barnes DM. Barkalow J. Plata DJ. Org. Lett.  2009,  11:  273