What functional groups are in 4-nitrophenol?

August 29, 2023

4-nitrophenol (CAS 100-02-7) is a widely studied compound in the field of chemistry due to its diverse applications in various fields, including analytical chemistry, environmental science, and pharmacology. The compound is a yellow crystalline solid that is soluble in water and organic solvents. It is commonly used as a model compound for studying the behavior of nitrophenols in various systems and for developing analytical methods for detecting and quantifying these compounds in environmental samples. In recent years, there has been a growing interest in the pharmacological properties of 4-nitrophenol, particularly its potential as an anticancer agent. Studies have shown that the compound exhibits significant cytotoxicity against various cancer cell lines, making it a promising candidate for further investigation as a potential therapeutic agent. However, further research is needed to fully understand the mechanisms underlying the compound's anticancer activity and to optimize its pharmacological properties for clinical use.

What functional groups are in 4-nitrophenol?

The functional groups present in 4-nitrophenol are a hydroxyl group (OH) and a nitro group (NO2). The hydroxyl group is attached to the benzene ring, while the nitro group is attached to the para position of the benzene ring, opposite to the hydroxyl group. These functional groups contribute to the compound's chemical reactivity and play a significant role in its various applications. The hydroxyl group, for example, allows for hydrogen bonding and enhances the compound's solubility in water and other polar solvents. The nitro group, on the other hand, introduces electron-withdrawing properties, which can affect the compound's acidity and reactivity in various chemical reactions.

To confirm the functional groups in 4-nitrophenol, you can perform a series of chemistry experiments. Here is a step-by-step procedure:

 

• Chemical test for phenol group:

a. Take a small amount of 4-nitrophenol in a test tube.

b. Add a few drops of ferric chloride solution (FeCl3).

c. Observe the color change. The formation of a colored complex (usually purple or green) indicates the presence of a phenol group.

• Chemical test for nitro group:

a. Take a small amount of 4-nitrophenol in a test tube.

b. Add a few drops of dilute hydrochloric acid (HCl).

c. Heat the mixture gently. d. Observe the evolution of nitrous fumes (NO2) or the formation of a yellow-orange precipitate, indicating the presence of a nitro group.

• Chemical test for hydroxyl group (alcohol):

a. Take a small amount of 4-nitrophenol in a test tube.

b. Add a few drops of sodium carbonate solution (Na2CO3) to make it alkaline.

c. Add a few drops of bromine water (Br2). d. Observe the decolorization of bromine water due to the reaction with the hydroxyl group, indicating the presence of an alcohol group.

• Chemical test for aromatic ring:

a. Take a small amount of 4-nitrophenol in a test tube.

b. Add a few drops of concentrated sulfuric acid (H2SO4).

c. Heat the mixture gently. d. Observe the formation of a dark-colored solution or a color change, indicating the presence of an aromatic ring.

The functional groups present in 4-nitrophenol contribute to its various uses in different fields.

Here are some of the uses of the functional groups in 4-nitrophenol:

Phenol group: The phenol group in 4-nitrophenol imparts its characteristic properties, such as its acidic nature and ability to form complexes. These properties are utilized in the following ways:

• 4-nitrophenol is used as a precursor in the synthesis of various pharmaceuticals, dyes, and pesticides.
• It is used as an intermediate in organic synthesis to produce other compounds with desired properties.
• The phenol group also allows 4-nitrophenol to act as an antioxidant and preservative in some cosmetic and personal care products.

Nitro group: The nitro group in 4-nitrophenol introduces reactivity and specific properties, leading to its applications in various fields:

• 4-nitrophenol is used as a starting material for the synthesis of explosives, such as trinitrophenol (TNP or picric acid).
• It is used as a reagent in organic synthesis to introduce the nitro group into other molecules.
• The nitro group also imparts certain optical and electronic properties to 4-nitrophenol, making it useful in spectroscopic analysis and as a chromophore in dyes.

Hydroxyl group (alcohol): The hydroxyl group in 4-nitrophenol serves multiple purposes:

• It allows 4-nitrophenol to form hydrogen bonds, making it soluble in water and other polar solvents.
• The hydroxyl group enables 4-nitrophenol to undergo various chemical reactions, such as esterification, oxidation, and reduction, making it a versatile intermediate in organic synthesis.

Aromatic ring: The presence of an aromatic ring in 4-nitrophenol contributes to its stability, reactivity, and specific properties. Some uses include:

• The aromatic ring allows 4-nitrophenol to participate in aromatic substitution reactions, making it useful in the synthesis of other aromatic compounds.
• The aromaticity of the ring contributes to the stability and UV absorption properties of 4-nitrophenol, making it suitable for applications in UV filters, sunscreens, and photoprotective agents.