1,2-Difluorobenzene

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1,2-Difluorobenzene^[1]

IUPAC name 1,2-difluoro-benzene
Other names 1,2-difluoro-benzene, o-difluorobenzene, ortho-difluorobenzene
Identifiers
CAS number	367-11-3^Y
PubChem	9706
ChemSpider	9325^Y
ChEBI	CHEBI:38583^Y
Jmol-3D images	Image 1
SMILES Fc1ccccc1F
InChI InChI=1S/C6H4F2/c7-5-3-1-2-4-6(5)8/h1-4H^Y Key: GOYDNIKZWGIXJT-UHFFFAOYSA-N^Y InChI=1/C6H4F2/c7-5-3-1-2-4-6(5)8/h1-4H Key: GOYDNIKZWGIXJT-UHFFFAOYAN
Properties
Molecular formula	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
Solubility in water	(insoluble) 1.14 g/L
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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, non-coordinating, and has a dielectric constant high enough to dissolve many electrolytes and metal complex salts. It is used instead of the common solvents for metal complexes acetonitrile, DMSO, and DMF because they can be coordinating.^[2]

References

↑ David R. Lide, ed., CRC Handbook of Chemistry and Physics, 89th Edition (Internet Version 2009), CRC Press/Taylor and Francis, Boca Raton, FL.
↑ 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.

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