1-Phenyl-1,2-propanedione
[CAS# 579-07-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: 1-Phenyl-1,2-propanedione
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.16
• CAS Registry Number: 579-07-7
• EC Number: 209-435-2
• FEMA: 3226
• SMILES: CC(=O)C(=O)C1=CC=CC=C1

Properties

• Density: 1.101
• Boiling point: 103-105 °C (14 mmHg)
• Refractive index: 1.53-1.534
• Flash point: 84 °C

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H312-H315-H317-H319-H332-H334-H335
• Safety Statements: P233-P260-P261-P264-P264+P265-P270-P271-P272-P280-P284-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P342+P316-P362+P364-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Skin sensitization	Skin Sens.	1	H317
Respiratory sensitization	Resp. Sens.	1	H334
Flammable liquids	Flam. Liq.	2	H225
Aspiration hazard	Asp. Tox.	1	H304

Discovery and Applications

1-Phenyl-1,2-propanedione, also known as benzoylacetone, is an important organic compound with a wide range of applications in various fields of chemistry and materials science. Its chemical formula is C10H10O3, and it features a phenyl group attached to a dione structure, making it a valuable compound in synthetic chemistry and industrial applications.

The discovery of 1-Phenyl-1,2-propanedione dates back to the early 20th century when organic chemists were exploring methods to synthesize and study compounds with unique functional groups. Its synthesis typically involves the condensation of benzoyl chloride with acetone in the presence of a base, resulting in the formation of this dione compound. Since its discovery, 1-Phenyl-1,2-propanedione has been studied extensively due to its versatile reactivity and application potential.

One of the primary applications of 1-Phenyl-1,2-propanedione is in the field of organic synthesis. The compound serves as an important intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its dione functionality allows it to participate in diverse chemical reactions, including cyclization and condensation reactions, which are crucial for the development of complex organic molecules. For example, 1-Phenyl-1,2-propanedione is used in the synthesis of a range of heterocyclic compounds, which are valuable in medicinal chemistry.

In addition to its role in organic synthesis, 1-Phenyl-1,2-propanedione is utilized in the production of dyes and pigments. The compound can be reacted with different nucleophiles to form colored products, which are then used in various applications, including textiles and coatings. The ability to fine-tune the electronic properties of 1-Phenyl-1,2-propanedione derivatives allows for the design of dyes with specific colors and properties, making it a useful compound in the colorant industry.

The compound is also employed in the production of chelating agents. 1-Phenyl-1,2-propanedione can form chelates with metal ions, creating stable complexes that are useful in a range of applications, including analytical chemistry and industrial processes. These chelates are often used as catalysts or reagents in various chemical reactions, highlighting the importance of 1-Phenyl-1,2-propanedione in both research and industrial settings.

Moreover, 1-Phenyl-1,2-propanedione has applications in the field of materials science. It is used as a building block in the synthesis of polymer materials and can be incorporated into polymer matrices to enhance the material's properties. The ability to modify the chemical structure of 1-Phenyl-1,2-propanedione allows researchers to tailor the physical and chemical properties of the resulting polymers, which can be applied in various industries, including electronics and packaging.

Despite its many uses, 1-Phenyl-1,2-propanedione must be handled with care due to its reactivity and potential health hazards. Proper safety protocols should be followed to minimize exposure and ensure safe handling of this compound in both laboratory and industrial settings.

In summary, 1-Phenyl-1,2-propanedione is a valuable compound with a wide range of applications in organic synthesis, dye production, chelating agent formation, and materials science. Its versatile reactivity and ability to form complex derivatives make it an essential compound in various fields of chemistry and industry.

References

2019. Bioinspired oxidation of oximes to nitric oxide with dioxygen by a nonheme iron(II) complex. Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry, 24(7).
DOI: 10.1007/s00775-019-01726-6

2019. Catalytic Strategies to Enantiopure Benzoins: Past and Future. Synthesis, 51(23).
DOI: 10.1055/s-0039-1691529

2021. Abiotic reduction of ketones with silanes catalysed by carbonic anhydrase through an enzymatic zinc hydride. Nature Chemistry, 13(3).
DOI: 10.1038/s41557-020-00633-7