1,2-Difluorobenzene, also known as DFB, is an

aromatic In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...

compound with formula CHF. This colorless flammable liquid is a

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

used in the

electrochemical Electrochemistry is the branch of physical chemistry concerned with the relationship between electrical potential difference and identifiable chemical change. These reactions involve electrons moving via an electronically conducting phase (typi ...

studies of transition metal complexes. Compared to most conventional halogenated aliphatic and aromatic solvents, it possesses an exceptionally high dielectric constant (ε₀ = 13.8 at 300 K). Thus, it can be a suitable solvent for cationic, and/or highly electrophilic organometallic complexes.

Synthesis

Difluorobenzenes can be prepared by the Balz-Schiemann reaction, which entails conversion of diazonium

tetrafluoroborate Tetrafluoroborate is the anion . This tetrahedral species is isoelectronic with tetrafluoroberyllate (), tetrafluoromethane (CF4), and tetrafluoroammonium () and is valence isoelectronic with many stable and important species including the perc ...

salts to their fluorides. The synthesis of 1,2-difluorobenzene starts with 2- fluoroaniline: : : The syntheses of 1,3- and 1,4-difluorobenzene proceed respectively from 1,3- and 1,4-diaminobenzene, which are doubly diazotized.

Laboratory applications

Organometallic Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and so ...

derivatives of 1,2-difluorobenzene have been well developed. It is found to be a weaker base than benzene. 1,2-Difluorobenzene has been used as solvent for the

analysis of transition metal complexes. It is relatively chemically inert, weakly coordinating and has a relatively high dielectric constant. In contrast to

acetonitrile Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not class ...

DMSO Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula . This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is ...

, and DMF it is a weakly coordinating solvent for metal complexes, . It has anaesthetic properties. 1,2-Difluorobenzene can be acylated to 3',4'-difluoropropiophenone.

References

{{DEFAULTSORT:Difluorobenzene, 1, 2- Fluorobenzenes Halogenated solvents Aromatic solvents