2-Amino-5-chloro-2'-fluorobenzophenone
[CAS# 784-38-3]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Ketone fragrance >> Aromatic ketone fragrance
• Name: 2-Amino-5-chloro-2'-fluorobenzophenone
• Molecular Formula: C₁₃H₉ClFNO
• Molecular Weight: 249.67
• CAS Registry Number: 784-38-3
• EC Number: 212-316-8
• SMILES: C1=CC=C(C(=C1)C(=O)C2=C(C=CC(=C2)Cl)N)F

Properties

• Melting point: 93-97 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-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
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Amino-5-chloro-2'-fluorobenzophenone is an organic compound with the formula C13H9ClFNO. This compound was first synthesized in the mid-20th century as part of research into halogenated benzophenones and their potential applications. It is typically produced through a series of chemical reactions starting with chlorination and fluorination of benzophenone derivatives, followed by amination. The discovery of 2-amino-5-chloro-2'-fluorobenzophenone provided researchers with a valuable intermediate for the synthesis of various organic compounds

In the pharmaceutical industry, 2-amino-5-chloro-2'-fluorobenzophenone serves as a key intermediate in the synthesis of various drugs. Its unique structure, which includes an amino group and halogen substituents, allows it to be used in the creation of molecules with specific biological activities. For instance, it can be used to synthesize compounds with potential anticancer, antiviral, and antibacterial properties. The presence of fluorine and chlorine atoms can enhance the metabolic stability and bioavailability of these drugs

This compound is also employed in the agrochemical sector for the development of pesticides, herbicides, and fungicides. The halogenated aromatic structure of 2-amino-5-chloro-2'-fluorobenzophenone allows for the creation of agrochemicals that can effectively target and control pests and diseases in crops.

In materials science, 2-amino-5-chloro-2'-fluorobenzophenone is used in the synthesis of advanced polymers and resins. Its reactivity allows it to be incorporated into polymer chains, enhancing properties such as thermal stability, chemical resistance, and mechanical strength.

2-Amino-5-chloro-2'-fluorobenzophenone is widely used in academic and industrial research to explore new synthetic methodologies and reaction mechanisms. Researchers use it as a model compound to study the effects of halogen substitution on aromatic compounds and to develop new synthetic routes for complex organic molecules.

The compound is also used in the production of dyes and pigments. The presence of an amino group and halogen atoms allows it to be used as a precursor for the synthesis of dyes with specific colors and properties. The ability to fine-tune the electronic properties of the dye molecules through halogen substitution makes this compound valuable in the dye industry.

References

2018. Improved and scalable methods for the synthesis of midazolam drug and its analogues using isocyanide reagents. Journal of the Iranian Chemical Society, 16(5).
DOI: 10.1007/s13738-018-1555-0

2008. Indium(III) Trifluoromethanesulfonate: An Efficient Reusable Catalyst for the Alkynylation-Cyclization of 2-Aminoaryl Ketones and Synthesis of 2,4-Disubstituted Quinolines. Synlett, 2008(4).
DOI: 10.1055/s-2008-1042800