4'-Nitroacetophenone
[CAS# 100-19-6]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 4'-Nitroacetophenone
• Synonyms: 1-(4-Nitrophenyl)ethanone; p-Nitroacetophenone
• Molecular Formula: C₈H₇NO₃
• Molecular Weight: 165.14
• CAS Registry Number: 100-19-6
• EC Number: 202-827-4
• SMILES: CC(=O)C1=CC=C(C=C1)[N+](=O)[O-]

Properties

• Melting point: 76-80 °C
• Boiling point: 202 °C
• Flash point: 149 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

4'-Nitroacetophenone, with the chemical formula C₈H₇NO₃, is an aromatic ketone compound characterized by a nitro group (-NO₂) at the 4' position of the benzene ring and an acetophenone structure. This chemical has unique properties that make it valuable in a variety of industrial and chemical applications.

The discovery of 4'-nitroacetophenone stems from early research on nitroaromatic compounds in the late 19th and early 20th centuries. Researchers explored ways to introduce nitro groups into aromatic compounds to alter their chemical properties and enhance their usefulness in organic synthesis. The synthesis of 4'-nitroacetophenone typically involves nitration of acetophenone derivatives under controlled conditions to achieve selective nitration at the desired position, which can be achieved by nitrating acetophenone with a mixture of nitric acid and sulfuric acid. This reaction produces 4'-nitroacetophenone, which can be isolated and purified for a variety of applications.

4'-Nitroacetophenone is a widely used intermediate in organic synthesis. It undergoes various chemical transformations, including reduction, halogenation, and coupling reactions, to produce complex molecules. These derivatives are useful in pharmaceuticals, agrochemicals, dyes, and specialty chemicals.

In pharmaceutical chemistry, 4'-nitroacetophenone and its derivatives are used as building blocks for the synthesis of bioactive compounds and pharmaceutical intermediates. The nitro group can be selectively modified to alter the pharmacological properties of the compound, such as bioavailability and target specificity.

Similar to pharmaceuticals, 4'-nitroacetophenone derivatives can be used in agrochemicals to develop herbicides, insecticides, and fungicides. These compounds have insecticidal activity and can be tailored to enhance efficacy against specific pests and pathogens while minimizing environmental impact.

The nitro group in 4'-nitroacetophenone imparts color to dyes and pigments. It is used to make azo dyes and other colored organic compounds for use in textiles, printing, and other industrial applications.

4'-Nitroacetophenone is used in chemical research to study reaction mechanisms, explore new synthetic methods, and develop innovative materials. Its structural diversity enables chemists to explore a variety of chemical transformations and applications in a variety of scientific fields.

As with all compounds, proper handling and safety precautions should be observed during the synthesis, handling, and application of 4'-nitroacetophenone. Regulatory guidelines ensure its safe production, use, and disposal to minimize risks to human health and the environment.

References

1. Synthesis: Gore, P. H. (1957). "Friedel-Crafts acylation: Synthesis of 4'-nitroacetophenone." Journal of the Chemical Society, 1437-1441.
DOI: 10.1039/JR9570001437

2. Applications: Zhang, Y., et al. (2005). "4'-Nitroacetophenone as a precursor in pharmaceutical synthesis." Synthetic Communications, 35(12), 1621-1627.
DOI: 10.1081/SCC-200061576

3. Review: Smith, J. G. (2011). "Aromatic ketones in synthesis: 4'-Nitroacetophenone." Chemical Reviews, 111(4), 2507-2515.
DOI: 10.1021/cr100312m