Synlett 2011(1): 139-140  
DOI: 10.1055/s-0030-1259092
© Georg Thieme Verlag Stuttgart ˙ New York

Tripotassium Phosphate: From Buffers to Organic Synthesis

Johant Lizel Lakey Beitia*
Escuela de Química and Centro de Investigaciones en Productos Naturales, Universidad de Costa Rica, 2060 San Pedro, San José, Costa Rica
Further Information

Publication History

Publication Date:
14 December 2010 (eFirst)


Tripotassium phosphate (potassium phosphate tribasic, K3PO4) is a strong inorganic base (pKa = 12.32 for the conjugate acid). It is non-toxic, very inexpensive, and available from many chemical supply companies. This chemical is used as a food additive or to form stable phosphate buffer solutions in water. However, it is soluble in organic solvents (both in polar and nonpolar), and thus has been used as an alternative non-nucleophilic base in several reactions.

The choice of base in an organic reaction depends on various factors. In several cases, a super strong base like n-BuLi is not needed for the deprotonation and chemists rely on weaker organic amines or inorganic salts. Organic amines (e.g., triethylamine, pyridine) are usually foul smelling liquids soluble in most solvents, but can cause problems with nucleophilic attack or coordination to metals. Inorganic salts used in organic synthesis include K2CO3 and Cs2CO3, although the former is only soluble in polar solvents and the latter is very expensive and can be moisture-sensitive. K3PO4 is slightly hygroscopic, but its melting point is 1380 ˚C so it can be easily heated to remove water without decomposition.


  • 1 Dandepally SR. Williams AL. Tetrahedron Lett.  2009,  50:  1071 
  • 2 Xu H. Chen Y. Molecules  2007,  12:  861 
  • 3 Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
  • 4 Ohe T. Miyaura N. Suzuki A. J. Org. Chem.  1993,  58:  2201 
  • 5 Fang G.-H. Yan Z.-J. Deng M.-Z. Org. Lett.  2004,  6:  357 
  • 6 Negishi E.-I. Anastasia L. Chem. Rev.  2003,  103:  1979 
  • 7 Shirakawa E. Kitabata T. Otsuka H. Tsuchimoto T. Tetrahedron  2005,  61:  9878 
  • 8 Beletskaya IP. Cheprakov AV. Chem. Rev.  2000,  100:  2009 
  • 9 Yao Q. Kinney EP. Yang Z. J. Org. Chem.  2003,  68:  7528 
  • 10 Hassan J. Sévignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev.  2002,  102:  1359 
  • 11a Niu J. Zhou H. Li Z. Xu J. Hu S. J. Org. Chem.  2008,  73:  7814 
  • 11b Niu J. Guo P. Kang J. Li Z. Xu J. Hu S. J. Org. Chem.  2009,  74:  5075 
  • 12 Wolfe JP. Buchwald SL. Angew. Chem. Int. Ed.  1999,  38:  2413 
  • 13 Farina V. Krishnamurthy V. Scott WJ. Org. React.  1998,  50:  1 
  • 14 Bedford RB. Cazin CSJ. Hazelwood SL. Chem. Commun.  2002,  2608 
  • 15 Lee S. Beare NA. Hartwig JF. J. Am. Chem. Soc.  2001,  123:  8410