2-nitrofluorene

2-Nitrofluorene

IUPAC Name:	2-Nitrofluorene
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Chemical formula	CHNO
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2-Nitrofluorene is an organic compound with the chemical formula C₁₃H₉NO₂. It is a derivative of fluorene, where a nitro group is substituted at the 2-position of the fluorene ring system. This compound is of interest in various fields, including environmental science and toxicology, due to its presence as a pollutant and its potential health effects.

Structure and Properties

2-Nitrofluorene is characterized by a planar polycyclic aromatic structure with a nitro group attached to the fluorene backbone. The presence of the nitro group significantly alters the electronic properties of the fluorene, making it more reactive in certain chemical environments. The compound appears as a yellow crystalline solid and is known for its low solubility in water, which affects its environmental distribution and persistence.

Synthesis

The synthesis of 2-nitrofluorene typically involves the nitration of fluorene using a mixture of concentrated nitric and sulfuric acids. This process introduces the nitro group selectively at the 2-position due to the electronic and steric effects of the fluorene ring system. The reaction must be carefully controlled to prevent over-nitration and to ensure high yield and purity of the desired product.

Applications and Uses

While 2-nitrofluorene itself is not widely used in industrial applications, it serves as an important intermediate in the synthesis of other chemical compounds. It is also used in research settings to study the behavior of nitroaromatic compounds in biological systems and the environment.

Environmental and Health Impacts

2-Nitrofluorene is considered a potential environmental pollutant, primarily due to its formation during the incomplete combustion of organic materials, such as fossil fuels and biomass. It is often detected in urban air, vehicle exhaust, and industrial emissions. The compound is of concern due to its potential mutagenic and carcinogenic properties, which have been observed in laboratory studies.

Safety and Handling

Due to its potential health effects, 2-nitrofluorene should be handled with care in laboratory and industrial settings. Appropriate personal protective equipment, such as gloves and goggles, should be used to minimize exposure. Additionally, measures should be taken to prevent environmental release and contamination.

Also see

• Fluorene
• Nitro compounds
• Polycyclic aromatic hydrocarbons
• Environmental pollutants