2-Amino-4'-fluorobenzophenone
[CAS# 3800-06-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: 2-Amino-4'-fluorobenzophenone
• Molecular Formula: C₁₃H₁₀NOF
• Molecular Weight: 215.23
• CAS Registry Number: 3800-06-4
• EC Number: 609-505-6
• SMILES: C1=CC=C(C(=C1)C(=O)C2=CC=C(C=C2)F)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.609, Calc.^*
• Boiling Point: 390.6±27.0 °C (760 mmHg), Calc.^*
• Flash Point: 190.0±23.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H315-H317-H319-H335-H411
• Safety Statements: P261-P264-P264+P265-P271-P272-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

2-Amino-4'-fluorobenzophenone is a specialized organic compound with applications primarily in medicinal and synthetic organic chemistry. Its structure is characterized by a benzophenone backbone, where a fluorine atom is substituted at the para-position of one phenyl ring, and an amino group is attached to the other ring. This unique arrangement of functional groups makes it a valuable intermediate in the synthesis of various pharmaceuticals, particularly in the development of anti-inflammatory and antimicrobial agents. The discovery of 2-amino-4'-fluorobenzophenone arose from research into modified benzophenones, which demonstrated versatile reactivity profiles and potential bioactivity.

The compound is highly valued as a key building block in drug synthesis due to its electrophilic ketone group and nucleophilic amino group, which facilitate a range of reactions including nucleophilic addition and condensation reactions. Medicinal chemists often incorporate 2-amino-4'-fluorobenzophenone into the synthesis of heterocyclic structures that can mimic biological molecules and bind selectively to receptors or enzymes. For instance, in the development of anti-inflammatory agents, this compound serves as a precursor to molecules that modulate inflammation pathways by interacting with key regulatory enzymes. Additionally, in the design of antimicrobial agents, the fluorine substitution enhances lipophilicity and metabolic stability, contributing to improved pharmacokinetic profiles for the resulting drugs.

Beyond medicinal chemistry, 2-amino-4'-fluorobenzophenone finds application in materials science. It acts as an intermediate in the synthesis of light-sensitive materials and UV-absorbing compounds, which are used in coatings and plastics to improve resistance to UV degradation. The compound’s benzophenone core absorbs UV light effectively, making it suitable for enhancing the longevity of products exposed to sunlight. Its incorporation into polymer chemistry also highlights its stability and utility, as it helps impart resistance to photo-induced changes in physical properties.

References

2022. Palladium-Catalyzed Synthesis of Polysubstituted Quinolines from 2-Aminophenyl Ketones and Internal Acetylenes. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-115-01058

2022. Synthesis from 2-Aminoaryl Ketones. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-115-01235

2006. Pitavastatin. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-16-0144