2Nitroanthracene

2-Nitroanthracene is an organic compound in the class of nitro-substituted polycyclic aromatic hydrocarbons (PAHs). It features an anthracene skeleton with a nitro group (–NO2) attached at the 2-position, giving the formula C14H9NO2. It is one of several isomeric nitroanthracenes, alongside 1-nitroanthracene and 9-nitroanthracene.

Production and sources: Commercially, 2-nitroanthracene is typically formed by nitration of anthracene under controlled mixed-acid conditions, often yielding a mixture of nitro isomers. It can also appear as a byproduct in related oxidation or functionalization processes. The compound is primarily used as an intermediate in the synthesis of dyes, pigments, and various organic compounds.

Properties: 2-Nitroanthracene is usually a pale yellow to orange crystalline solid at room temperature with limited water solubility and greater solubility in organic solvents. The nitro group strongly influences the electronic properties of the ring system and can be reduced to yield 2-aminanthracene. The compound absorbs in the UV region and its electronic characteristics are affected by nitro substitution at the 2-position.

Applications and reactions: It serves as a versatile precursor for the preparation of amines and related derivatives used in dye chemistry and organic synthesis. Reduction of 2-nitroanthracene affords 2-aminanthracene, a useful building block in the production of dyes and pharmaceuticals. Nitro PAHs, including nitroanthracenes, are also studied in environmental chemistry and photochemical research.

Safety: 2-Nitroanthracene is a hazardous chemical. It may be harmful if inhaled, ingested, or absorbed through the skin and can be persistent in the environment. It is considered potentially mutagenic or carcinogenic in some contexts. Handling requires appropriate personal protective equipment, good ventilation, and proper disposal in accordance with regulatory guidelines.