Synlett 2007(8): 1326-1327  
DOI: 10.1055/s-2007-980340
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Hydroxylamine Hydrochloride

Moyurima Borthakur*
Medicinal Chemistry Division, Regional Research Laboratory, ­Jorhat 785006, Assam, India
e-Mail: moyurima27@rediffmail.com;
Further Information

Publication History

Publication Date:
08 May 2007 (online)

Introduction

Hydroxylamine hydrochloride is a hygroscopic white crystalline powder (mp 151-152 °C). Explosion of the reagent may occur if it is heated above 115 °C. Hydroxyl­amine hydrochloride is harmful if inhaled or swallowed and it is irritating to eyes, skin, and respiratory tract. [1] The reagent decomposes slowly on contact with moisture and should not be stored above 65 °C. Hydroxylamine as a free base is available in the form of large white flakes or needles; however, due to its instability, commercially available hydroxylamine hydrochloride is used as a stable source of hydroxylamine. [2] This versatile reagent can be prepared by treatment of sulfur dioxide with a cold ­solution of potassium nitrate and potassium acetate under controlled reaction conditions below 0 °C.

For over a century, hydroxylamine hydrochloride has found wide application in organic synthesis including electrophilic substitution reactions, [1] oximation, [3] the ­synthesis of pyrazoles, [4] nitriles, [5] isoxazoles, [6] pyridines, [7] nitrones, [8] etc. It is also used as reducing agent [9] and its importance in areas like bioorganic and medicinal chemistry is also vivid. For example, this reagent greatly facilitates the synthesis of a new class of glycosylated β-amino ­acids, which exhibit good activity against human anti-­malarial parasite Plasmodium falciparum.10

    References

  • 1 Encyclopedia of Reagents for Organic Synthesis   Vol. 4:  Paquette LA. John Wiley & Sons; Chichester: 1995.  p.2760-2764  
  • 2 Handbook of Inorganic Compounds   Perry DL. Phillips SL. CRC Press; Boca Raton: 1995.  p.196 
  • 3 Wu M. Chen R. Huang Y. Synthesis  2004,  2441 
  • 4 Saikia A. Barthakur MG. Borthakur M. Saikia CJ. Bora U. Boruah RC. Tetrahedron Lett.  2006,  47:  43 
  • 5 Ballini R. Fiorini D. Palmieri A. Synlett  2003,  1841 
  • 6a Hansen TV. Wu P. Fokin VV. J. Org. Chem.  2005,  70:  7761 
  • 6b Gupta R. Pathak D. Jindal DP. Eur. J. Med. Chem.  1999,  34:  659 
  • 7 Jun J. Shin HS. Kim SH. J. Chem. Soc., Perkin Trans. 1  1993,  71:  1815 
  • 8 Cicchi S. Marradi M. Vogel P. Goti A. J. Org. Chem.  2006,  71:  1614 
  • 9 Gangadhar A. Rao TC. Subbarao R. Lakshminarayana G. J. Am. Oil Chem. Soc.  1989,  66:  1507;   Chem. Abstr. 1990, 112, 22677j
  • 10 Mishra RC. Tripathi R. Katiyar D. Tewari N. Singh D. Tripathi RP. Bioorg. Med. Chem.  2003,  11:  5363 
  • 11 Kumar V. Aggarwal R. Singh SP. J. Fluorine Chem.  2006,  127:  880 
  • 12 Gregoire CS. Travert N. Zaparucha A. Mourabit A. Org. Lett.  2006,  8:  2961 
  • 13 Sarodnick G. Heydenreich M. Linker T. Kleinpeter E. Tetrahedron  2003,  59:  6311