1,2-Difluorobenzene

1,2-Difluorobenzene^[1]

Names
Preferred IUPAC name 1,2-Difluorobenzene
Other names o-Difluorobenzene ortho-Difluorobenzene
Identifiers
CAS Number	367-11-3
3D model (Jmol)	Interactive image
ChEBI	CHEBI:38583
ChemSpider	9325
ECHA InfoCard	100.006.074
PubChem	9706
InChI InChI=1S/C6H4F2/c7-5-3-1-2-4-6(5)8/h1-4H Key: GOYDNIKZWGIXJT-UHFFFAOYSA-N InChI=1/C6H4F2/c7-5-3-1-2-4-6(5)8/h1-4H Key: GOYDNIKZWGIXJT-UHFFFAOYAN
SMILES Fc1ccccc1F
Properties
Chemical formula	C6H4F2
Molar mass	114.093 g/mol
Appearance	colorless liquid
Density	1.1599 g/cm^3
Melting point	−34 °C (−29 °F; 239 K)
Boiling point	92 °C (198 °F; 365 K)
Solubility in water	(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

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

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

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