1,2-Difluorobenzene

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1,2-Difluorobenzene[1]
O-Difluorobenzene.svg
Difluorobenzene molecule
Names
Preferred IUPAC name
1,2-Difluorobenzene
Other names
o-Difluorobenzene
ortho-Difluorobenzene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.074
Properties
C6H4F2
Molar mass 114.093 g/mol
Appearance colorless liquid
Density 1.1599 g/cm3
Melting point −34 °C (−29 °F; 239 K)
Boiling point 92 °C (198 °F; 365 K)
(insoluble) 1.14 g/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,2-Difluorobenzene, also known as DFB, is an aromatic compound with formula C6H4F2. This colorless liquid is a solvent used in the electrochemical studies of transition metal complexes.

Synthesis[edit]

1,2-Difluorobenzene is prepared by a simple substitution reaction of fluorine with fluorobenzene.

C6H5F + F2 → C6H4F2 + HF

The 1,4-isomer and small amounts of the 1,3-isomer are also produced in the reaction as the fluorine group on the aromatic ring of fluorobenzene is ortho- and para- directing.

Applications[edit]

1,2-Difluorobenzene has been used as solvent for the electrochemical analysis of transition metal complexes. It is relatively chemically inert, weakly coordinating, and has a dielectric constant high enough to dissolve many electrolytes and metal complex salts, it is used as a weakly coordinating solvent for metal complexes, alternative to the relatively more strongly coordinating solvents acetonitrile, DMSO, and DMF.[2]

1,2-Difluorobenzene can be acylated to 3',4'-difluoropropiophenone, which has interesting application in the synthesis of halogenated cathinone/PPA congeners.[3]

References[edit]

  1. ^ David R. Lide, ed., CRC Handbook of Chemistry and Physics, 89th Edition (Internet Version 2009), CRC Press/Taylor and Francis, Boca Raton, FL.
  2. ^ O'toole, Terrence R.; Younathan, Janet N.; Sullivan, B. Patrick; Meyer, Thomas J. (1989). "1,2-Difluorobenzene: a relatively inert and noncoordinating solvent for electrochemical studies on transition-metal complexes". Inorganic Chemistry. 28 (20): 3923. doi:10.1021/ic00319a032. 
  3. ^ GB 1140754