Cover Image

Solubility of phenylboronic compounds in water

Andrzej Sporzynski, Pawel Leszczynski

Abstract


Solubility of six phenylboronic compounds in water was investigated using different methods. The results are consistent with each other, although for particular compounds selected methods should be preferred. The solubility of the investigated compounds is low, with the value of ca. 2 g/100 cm3 H2O at 20°C for unsubstituted phenylboronic acid. The unsubstituted benzoxaborole is less soluble than phenylboronic acid. Introduction of OiBu, COOH and CF3 groups into the phenyl ring decreases solubility in comparison with unsubstituted phenylboronic acid, especially for the alkoxy substituent.


Full Text:

PDF

References


- N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457-2483.

- Boronic Acids. Preparation and Applications in Organic Synthesis, Medicine and Materials, second ed., D.G. Hall (Ed.), Wiley-VCH, Weinheim, 2011.

- S. Sene, M.A. Pizzoccaro, J. Vezzani, M. Reinholdt, P. Gaveau, D. Berthomieu, S. Bégu, C. Gervais, C. Bonhomme, G. Renaudin, A. Mesbah, A. van der Lee, M.E. Smith and D. Laurencin, Crystals, 2016, 6, 48.

- A. Adamczyk-Woźniak, K.M. Borys and A. Sporzyński, Chem. Rev., 2015, 115, 5224-5247.

- R.I. Khan and K. Pitchumani, Green Chem., 2016, 18, 5518-5528.

- R.M. Washburn, E. Levens, C.F. Albright and F.A. Billig, Org. Synth. Coll. Vol., 1963, Vol. IV, p. 71.

- H. Firouzabadi, N. Iranpoor, A. Ghaderi, M. Gholinejad, S. Rahimi and S. Jokar, RSC Adv., 2014, 4, 27674-27682.

- M. Dowlut and D.G. Hall, J. Am. Chem. Soc., 2006, 128, 4226-4227.

- - (a) U. Domańska, J. Serwatowski, A. Sporzyński, M. Dąbrowski, Thermochim.Acta, 1993, 222, 279-290; (b) U. Domańska, J. Serwatowski, A. Sporzyński, M. Dąbrowski, Thermochim. Acta, 1995, 249, 127-142; (c) M. Dąbrowski, U. Domańska, J. Serwatowski,

A. Sporzyński, Thermochim. Acta, 1995, 250, 19-27; (d) M. Dąbrowski, J. Serwatowski, A. Sporzyński, Thermochim. Acta, 1996, 288, 191-202; (e) M. Dąbrowski, J. Serwatowski, A. Sporzyński, J. Chem. Eng. Data, 1997, 42, 1111-1115; (f) M. Dąbrowski, J. Serwatowski,

. Sporzyński, Pol. J. Chem., 1998, 72, 2423-2431.

- A. Adamczyk-Woźniak, I. Madura, A. Pawełko, A. Sporzyński, A. Żubrowska, J. Żyła, Cent. Eur. J. Chem., 2011, 9, 199-205.

- P. Kurach, S. Luliński, J. Serwatowski, Eur. J. Org. Chem., 2008, 18, 3171-3178.

- 12- A. Adamczyk-Woźniak, Z. Brzózka, M. Dąbrowski, I. D. Madura, R. Scheidsbach, E. Tomecka, K. Żukowski, A. Sporzyński, J. Mol. Struct., 2013, 1035, 190-197.

- T. Hofman, M. Reda and M. Gliński, Fluid Phase Equil., 2013, 356, 271-276.

- C. Achard, M. Jaoui, M. Schwing and M. Rogalski, J. Chem. Eng. Data 1996, 41, 504-507.

- W. A. Marinaro, L.J. Schieber, E.J. Munson, V.W. Day and V. J. Stella, J. Pharm. Sci., 2012, 1010, 3190-3198.

- A. Matuszewska, M. Uchman, A. Adamczyk-Woźniak, A. Sporzyński, S. Pispas, L. Kovacik, M. Stepanek, Biomacromolecules, 2015, 16, 3731-3739.




DOI: http://dx.doi.org/10.13171/mjc65/01711030630-sporzynski

Refbacks

  • There are currently no refbacks.


Copyright (c) 2017 Mediterranean Journal of Chemistry