Synlett 2011(6): 881-882  
DOI: 10.1055/s-0030-1259911
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Hexamethyldisilazane

Xiang Deng*a,b
a Department of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Sichuan Dazhou 635000, P. R. of China
b School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. of China
e-Mail: qwj616@swu.edu.cn;
Further Information

Publication History

Publication Date:
16 March 2011 (online)

Introduction

Hexamethyldisilazane (HMDS) is a colorless liquid with an ammonia odor. It is a versatile silylating agent, which can react with alcohols, acids, amines, thiols, phenols, amides, thioamides, sulfonamides, and enolizable ketones. Ammonia, the by-product of the reaction, can be readily removed from the reaction medium. In the past few years, applications of hexamethyldisilazane have been quite extensive, especially in the field of organic synthesis, manufactures of medicines and industry. Hexa­methyldisilazane is used as valuable raw material for antisclerotic and antineoplastic drugs as well as synthetic antibiotics, such as amikacin, ftorafur, parmidin, penicillin, etc. It is usually used as a surface treatment agent for diatomite, silica, and titanium powder. Further, it is used as a cohesive aid for light-etching agents in semiconductor industry. It can be used in prime treatment for hard-coatings on plastics and in the syntheses of cross-linked resins. In general, hexamethyldisilazane is commercially available and can also be easily prepared according to the reported procedures [¹] (Scheme  [¹] ).

Scheme 1

    References

  • 1 Chernyak SV. Yatluk YuG. Suvorov AL. Russ. J. Gen. Chem.  2000,  70:  1313 
  • 2 Kadam ST. Kim SS. J. Organomet. Chem.  2009,  694:  2562 
  • 3 Lu H. Cheng JJ. J. Am. Chem. Soc.  2008,  130:  12562 
  • 4a Ghorbani-Vaghei R. Zolfigol MA. Chegeny M. Veisi H. Tetrahedron Lett.  2006,  47:  4505 
  • 4b Risto M. Assoud A. Winter SM. Oilunkaniemi R. Laitinen RS. Oakley RT. Inorg. Chem.  2008,  47:  10100 
  • 5 Denmark SE. Edwards MG. J. Org. Chem.  2006,  71:  7293 
  • 6 Moon JT. Jeon JY. Park HA. Noh YS. Lee KT. Kim J. Choo DJ. Lee JY. Bioorg. Med. Chem.Lett.  2010,  20:  734 
  • 7 Azizi N. Rajabi F. Saidi MR. Tetrahedron Lett.  2004,  45:  9233 
  • 8 Song QY. Yang BL. Tian SK. J. Org. Chem.  2007,  72:  5407