Dibenzoylmethane
[CAS# 120-46-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: Dibenzoylmethane
• Synonyms: 1,3-Diphenyl-1,3-propanedione; 1,3-Diphenylpropane-1,3-dione
• Molecular Formula: C₁₅H₁₂O₂
• Molecular Weight: 224.26
• CAS Registry Number: 120-46-7
• EC Number: 204-398-9
• SMILES: C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=CC=C2

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 75-79 °C
• Index of Refraction: 1.584, Calc.^*
• Boiling Point: 357.4±0.0 °C (760 mmHg), Calc.^*, 219-221 °C (18 mmHg)
• Flash Point: 146.9±20.2 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317
• Safety Statements: P261-P272-P280-P302+P352-P321-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Dibenzoylmethane, also known as benzoylacetone, is an organic compound with the molecular formula C15H12O2. It is characterized by the presence of two benzoyl groups attached to a methylene bridge. The compound is notable for its versatile applications in various fields, including organic synthesis, materials science, and cosmetic formulations. Dibenzoylmethane was first synthesized in the early 20th century as part of research aimed at exploring diketones and their derivatives, which have garnered interest for their unique chemical properties and potential uses.

The synthesis of dibenzoylmethane typically involves the condensation reaction between benzoyl chloride and acetylacetone in the presence of a suitable base. This method allows for the efficient production of dibenzoylmethane while maintaining high yields. The compound's structure enables it to function as a chelating agent and a precursor for further chemical transformations, making it a valuable intermediate in organic synthesis.

One of the primary applications of dibenzoylmethane lies in the field of organic photochemistry, where it is utilized as a UV filter in cosmetic and sunscreen products. Its ability to absorb ultraviolet light makes it effective in protecting the skin from harmful UV radiation, which is a significant factor in skin aging and the development of skin cancer. The incorporation of dibenzoylmethane in sunscreen formulations enhances their effectiveness by providing broad-spectrum protection against UVB and UVA rays.

In addition to its use in cosmetics, dibenzoylmethane has found applications in the field of polymer chemistry. It serves as a stabilizer in polymer formulations, preventing degradation caused by UV exposure. This property is particularly beneficial in the production of plastics and coatings, where prolonged exposure to sunlight can lead to discoloration and loss of mechanical properties. The incorporation of dibenzoylmethane in these materials extends their lifespan and maintains their aesthetic appeal.

Dibenzoylmethane is also utilized in the synthesis of various pharmaceutical compounds. Its structural features allow for modifications that can lead to the development of new drug candidates with enhanced biological activity. Research has indicated that derivatives of dibenzoylmethane exhibit anti-inflammatory, antioxidant, and anticancer properties, making them subjects of interest in drug discovery and development. The versatility of dibenzoylmethane as a building block in medicinal chemistry underscores its importance in the pharmaceutical industry.

Despite its numerous applications, the safety and environmental impact of dibenzoylmethane must be considered. Regulatory agencies, such as the U.S. Food and Drug Administration (FDA) and the European Chemicals Agency (ECHA), evaluate the safety of chemical substances used in consumer products. It is crucial for manufacturers to conduct thorough safety assessments and ensure compliance with relevant regulations to mitigate potential risks associated with the use of dibenzoylmethane in cosmetic and pharmaceutical applications.

As the demand for effective UV filters and stabilizers in various industries continues to grow, the role of dibenzoylmethane is likely to expand. Ongoing research focuses on improving its performance and exploring new applications, particularly in sustainable formulations and innovative materials. The development of safer and more effective derivatives of dibenzoylmethane will further enhance its relevance in the cosmetic and pharmaceutical sectors.

In conclusion, dibenzoylmethane is a valuable compound with significant applications in cosmetics, polymer chemistry, and pharmaceuticals. Its discovery and subsequent utilization reflect the importance of organic compounds in developing effective solutions for various industry challenges. Continued research into dibenzoylmethane's properties and applications will ensure its role as a key player in the advancement of materials and health-related products.

References

2005. Nanotubes from Isomeric Dibenzoylmethane Molecules. Chemistry (Weinheim an der Bergstrasse, Germany).
DOI: 10.1002/chem.200401265

2017. Dibenzoylmethane Protects Against CCl4-Induced Acute Liver Injury by Activating Nrf2 via JNK, AMPK, and Calcium Signaling. The AAPS Journal.
DOI: 10.1208/s12248-017-0133-1

2009. Photodegradation of Dibenzoylmethanes: Potential Cause of Photocontact Allergy to Sunscreens. Chemical Research in Toxicology.
DOI: 10.1021/tx900284e