Benzophenone
[CAS# 119-61-9]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Ketone fragrance >> Aromatic ketone fragrance
• Name: Benzophenone
• Synonyms: Diphenyl ketone; Diphenylmethanone
• Molecular Formula: C₁₃H₁₀O
• Molecular Weight: 182.22
• CAS Registry Number: 119-61-9
• EC Number: 204-337-6
• FEMA: 2134
• SMILES: C1=CC=C(C=C1)C(=O)C2=CC=CC=C2

Properties

• Density: 1.11
• Melting point: 47-49 ºC
• Boiling point: 305 ºC
• Refractive index: 1.5893
• Flash point: 143 ºC
• Water solubility: insoluble (<0.1 g/100 mL at 25 ºC)

Safety Data

• Hazard Symbols: GHS08;GHS09 Warning
• Hazard Statements: H373-H411
• Precautionary Statements: P260-P273-P319-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - single exposure	STOT SE	3	H335
Carcinogenicity	Carc.	1B	H350
Carcinogenicity	Carc.	2	H351
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1B	H317

Discovory and Applicatios

Benzophenone, a versatile organic compound, has been a significant player in various industrial and scientific applications due to its unique chemical properties. This aromatic ketone, with the molecular formula C₁₃H₁₀O, was first synthesized in the early 19th century, and its discovery marked a notable advancement in organic chemistry.

The synthesis of benzophenone can be traced back to its early preparation by the oxidation of benzoin, a process that involves converting benzoin to benzophenone using oxidizing agents. This compound quickly garnered attention due to its distinctive photochemical and photophysical properties, making it valuable in multiple domains.

One of the primary applications of benzophenone is as a UV filter in sunscreens and cosmetic products. Its ability to absorb ultraviolet light and protect the skin from harmful UV radiation makes it an essential ingredient in sun protection formulations. By absorbing UV radiation, benzophenone helps to prevent skin damage and reduce the risk of skin cancer, contributing to safer and more effective sunscreen products.

In addition to its use in personal care products, benzophenone is employed as a photoinitiator in polymer chemistry. In UV-curable systems, it facilitates the polymerization process by generating reactive species upon exposure to UV light. This property makes it a crucial component in the formulation of UV-cured coatings, inks, and adhesives. The compound's role in these applications includes enhancing the curing process and improving the durability and performance of the final products.

Benzophenone also serves as an intermediate in the synthesis of other chemical compounds, including pharmaceuticals and dyes. Its chemical structure provides a foundation for the development of various derivatives, which are used to produce a wide range of specialty chemicals.

Despite its many applications, the use of benzophenone is subject to regulatory scrutiny due to potential health and environmental concerns. Studies have shown that high concentrations of benzophenone can pose risks, leading to regulations that limit its use in consumer products. Consequently, ongoing research aims to find safer alternatives and mitigate potential risks associated with its use.

Overall, the discovery and application of benzophenone highlight its importance in diverse fields, from skincare to materials science. Its role as a UV filter, photoinitiator, and chemical intermediate underscores its versatility and impact across various industries.

References

2003. Application of stir bar sorptive extraction for wine analysis. Analytical and Bioanalytical Chemistry.
DOI: 10.1007/s00216-003-1837-x

2010. Rapid multi-analyte quantification of benzophenone, 4-methylbenzophenone and related derivatives from paperboard food packaging. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment.
DOI: 10.1080/19440049.2010.502130

2012. Synthesis, Biological Evaluation and Mechanism Studies of Deoxytylophorinine and Its Derivatives as Potential Anticancer Agents. PLoS ONE.
DOI: 10.1371/journal.pone.0030342