Hydrazine Hydrate (NH₂NH₂·H₂O)

Introduction

The synthetic utilities of hydrazine hydrate have been extensively investigated in organic chemistry. Among reducing agents, hydrazine hydrate stands out for its application to a broad variety of reductive transformations. It is easy to use and reduces many functional groups, such as carbonyl compounds, alkenes, alkynes and nitro groups under mild reaction conditions. Hydrazine hydrate is commercially available. It is a liquid (mp -52 °C, bp 120-121 °C, d = 1.027 g/mL), and is ­soluble in water, ethanol, methanol, propanol and iso­butanol.

References

• 1a Todd D. Org. React.  1948,  4:  378 
• 1b Szmant HH. Angew. Chem., Int. Ed. Engl.  1968,  7:  120 
• 1c Reusch W. Reduction   Dekker; New York: 1968.  p.171-185 
• 1d Clark C. Hydrazine   Mathieson Chemical Corp.; Baltimore: 1953. 
• 2a Huang-Minlon . J. Am. Chem. Soc.  1946,  68:  2487 
• 2b Huang-Minlon . J. Am. Chem. Soc.  1949,  71:  3301 
• 2c Durham LJ. Mcleod DJ. Cason J. Org. Synth. Coll. Vol. IV  1963,  510 
• 2d Hunig S. Lucke E. Brenningesr W. Org. Synth.  1963,  43:  34 
• 3a Furst A. Berlo RC. Hooton S. Chem. Rev.  1965,  65:  51 
• 3b Ayynger NR. Lugade AC. Nikrad PV. Sharma VK. Synthesis  1981,  640 
• 4a Pietra S. Ann. Chim. (Rome)  1955,  45:  850 
• 4b Rondestvedt Jr. CS. Johnson TA. Chem. Eng. News  1977,  55 (27):  38 
• 4c Bavin PMG. Org. Synth.  1960,  40:  5 
• 5 Weiser HB. Milligan WO. Cook EL. Inorg. Synth.  1946,  215 
• 6 Gowda S. Gowda DC. Indian J. Chem., Sect. B  2003,  42:  180 
• 7 Srinivasa GR. Abiraj K. Gowda DC. Indian J. Chem., Sect. B  2003,  42:  2885 
• 8 Schonberg A. Fateen AEK. Sammour AEMA. J. Am. Chem. Soc.  1957,  79:  6020 
• 9 Baltzly R. Mehta NB. Russell PB. Brooks RE. Grivsky EM. Steinberg AM. J. Org. Chem.  1961,  26:  3669 
• 10 Barton DHR. Basiardes G. Fourrey J.-L. Tetrahedron Lett.  1983,  24:  1605 
• 11 Barton DHR. Basiardes G. Fourrey J.-L. Tetrahedron Lett.  1984,  25:  1287 
• 12a Dupont V. Lecoq A. Mangeot JP. Aubry A. Boussard G. Marraud M. J. Am. Chem. Soc.  1993,  115:  8898 
• 12b Allcock SJ. Gilchrist TL. Shuttleworth SJ. King FD. Tetrahedron  1991,  47:  10053 
• 13a Yale HL. Losee K. Martins J. Holsing M. Perry FM. Bernstein J. J. Am. Chem. Soc.  1953,  75:  1933 
• 13b Bruice TC. Benkovic SJ. J. Am. Chem. Soc.  1964,  86:  418 
• 14 Toda F. Hyoda S. Okada K. Hirotsu K. J. Chem. Soc., Chem. Commun.  1995,  1531 
• 15 Peng Y. Song G. Green Chem.  2001,  3:  302 
• 16 Myers AG. Zheng B. J. Am. Chem. Soc.  1996,  118:  4492 
• 17 Myers AG. Zheng B. Tetrahedron Lett.  1996,  37:  4841