9nitroanthracene

9-Nitroanthracene is an aromatic nitro compound derived from anthracene by substitution of a hydrogen with a nitro group at the 9-position. Its molecular formula is C14H9NO2, and its structure consists of the three fused benzene rings of anthracene bearing a nitro substituent on the central ring.

The compound is typically prepared by the nitration of anthracene using mixed acids, such as concentrated sulfuric and nitric acids. Under controlled conditions, the nitro group preferentially adds to the 9-position, yielding 9-nitroanthracene as the major product, with smaller amounts of other nitro isomers possible. The chemistry of 9-nitroanthracene centers on the reactivity of the nitroarene moiety, which can undergo reduction to yield amines and allow access to a variety of derivatives.

Physically, 9-nitroanthracene is described as a pale yellow to orange crystalline solid. It is poorly soluble in water and more soluble in many organic solvents, including dichloromethane, chloroform, and toluene, reflecting the hydrophobic nature of the polycyclic aromatic system.

In terms of use, 9-nitroanthracene serves as an intermediate in organic synthesis. It can be reduced to 9-aminanthracene, a widely used building block for dyes, pigments, and related materials. The nitro group also provides a handle for further functionalization to prepare a variety of anthracene derivatives for research in dye chemistry and photophysics.

Safety considerations include handling as a potentially hazardous nitroaromatic compound. It can be irritating to skin and eyes and may pose inhalation risks; work should be conducted with appropriate personal protective equipment and in a fume hood, with waste disposed according to applicable regulations.