4-Nitrophenol

An organic compound with the formula C_H_NO_

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4-Nitrophenol is an organic compound with the formula C_H_NO_. It is a pale yellow solid that is a common intermediate in the synthesis of various chemical compounds. It is one of the three isomers of nitrophenol, the others being 2-nitrophenol and 3-nitrophenol.

Structure and properties

4-Nitrophenol consists of a phenolic ring substituted with a nitro group at the para position. This arrangement gives it distinct chemical properties, including its acidic nature and its ability to participate in various chemical reactions.

The presence of the nitro group makes 4-nitrophenol more acidic than phenol itself, as the nitro group is an electron-withdrawing group that stabilizes the phenoxide ion formed upon deprotonation.

Synthesis

4-Nitrophenol can be synthesized by the nitration of phenol. The reaction involves the substitution of a hydrogen atom on the phenol ring with a nitro group, typically using a mixture of concentrated nitric acid and sulfuric acid.

Nitration of phenol to produce 4-nitrophenol

Applications

4-Nitrophenol is used as a precursor in the synthesis of pharmaceuticals, pesticides, and dyes. It is also used as a standard for calibrating spectrophotometers due to its well-defined absorption peak in the ultraviolet-visible spectrum.

Safety and environmental impact

4-Nitrophenol is considered hazardous and can be harmful if ingested, inhaled, or absorbed through the skin. It is also an environmental pollutant, and its presence in industrial waste can lead to contamination of water sources.

Related pages

• Phenol
• Nitrophenol
• Nitration
• Spectrophotometry

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  Sample of 4-Nitrophenol

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  Diagram of Phenol Nitration