4-Chlorobenzophenone
[CAS# 134-85-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: 4-Chlorobenzophenone
• Synonyms: p-Chlorobenzophenone; (4-Chlorophenyl)phenyl-methanone
• Molecular Formula: C₁₃H₉ClO
• Molecular Weight: 216.67
• CAS Registry Number: 134-85-0
• EC Number: 205-160-7
• SMILES: C1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)Cl

Properties

• Melting point: 75-77 °C
• Boiling point: 195-196 °C (17 torr)
• Flash point: 143 °C

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H315-H319-H335-H400-H410
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

Discovery and Applications

4-Chlorobenzophenone, a derivative of benzophenone, is an important chemical compound with various applications in organic synthesis and material science. Characterized by the presence of a chlorine atom attached to the para position of one of the phenyl rings, this compound is known for its distinct chemical properties and functional versatility.

The discovery of 4-chlorobenzophenone arose from research into benzophenone derivatives aimed at enhancing or modifying their chemical properties. Benzophenone itself was first synthesized in the late 19th century, and subsequent studies explored various substitutions on the benzophenone framework to alter its reactivity and utility. The introduction of a chlorine atom at the para position resulted in a compound with unique properties and applications.

One of the primary uses of 4-chlorobenzophenone is as an intermediate in organic synthesis. Its structure makes it a valuable building block in the synthesis of more complex organic molecules. It is often employed in the production of pharmaceuticals, agrochemicals, and other fine chemicals where it serves as a precursor to more complex compounds. The chlorine substituent enhances the compound's reactivity, making it a useful intermediate in various chemical transformations.

In addition to its role in organic synthesis, 4-chlorobenzophenone finds application in the field of material science. It is used as a UV filter and stabilizer in polymers and coatings. By absorbing ultraviolet (UV) radiation, 4-chlorobenzophenone helps protect materials from UV-induced degradation, such as discoloration and structural damage. This property is particularly valuable in the manufacture of plastics and coatings that are exposed to sunlight.

The compound is also employed in the synthesis of specialty chemicals and as a reagent in analytical chemistry. Its reactivity and ability to participate in various chemical reactions make it a useful tool in research and development.

Despite its useful properties, there are considerations regarding the safety and environmental impact of 4-chlorobenzophenone. As with many chlorinated compounds, there is concern about its potential effects on human health and the environment. Research into the environmental fate and potential health impacts of 4-chlorobenzophenone is ongoing, and there is a focus on ensuring safe use and developing alternatives with better safety profiles.

Overall, 4-chlorobenzophenone is a significant chemical compound with valuable applications in organic synthesis, material science, and analytical chemistry. Its role in improving the performance and durability of materials and its utility as a chemical intermediate underscore its importance in modern chemistry.

References

2017. Transition-Metal- and Halogen-Free Oxidation of Benzylic sp3 C-H Bonds to Carbonyl Groups Using Potassium Persulfate. Synthesis, 49(15).
DOI: 10.1055/s-0036-1588429

2018. Acyl Radical Chemistry via Visible-Light Photoredox Catalysis. Synthesis, 51(06).
DOI: 10.1055/s-0037-1610329

2021. Recent Advances in the Synthesis of Diverse Libraries of Small-Molecule Building Blocks in Ionic Liquids (ILs). Synlett, 32(17).
DOI: 10.1055/s-0040-1719852