2-(1-bromoethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one | CAS 1408087-79-5

OVERVIEW

Chemical Name: 2‑(1‑bromoethyl)‑5‑fluoro‑3‑(3‑fluorophenyl)‑4H‑chromen‑4‑one
CAS Number: 1408087‑79‑5
Molecular Formula: C17H11BrF2O2
Molecular Weight: 365.17 g/mol (approx.)
Synonyms:

• 5‑Fluoro‑3‑(3‑fluorophenyl)‑2‑(1‑bromoethyl)‑4H‑chromen‑4‑one

• Bromoethylfluorochromenone derivative

• Fluorophenyl bromochromenone

2-(1-bromoethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one | CAS 1408087-79-5 is an advanced fluorinated chromenone derivative featuring multiple aromatic moieties and a bromine substituent. Its unique structural attributes make it valuable as an intermediate in medicinal chemistry, fluorine‑enabled property modulation studies, and synthetic methodology research.

CHEMICAL STRUCTURE & FEATURES

Structural Highlights:

• Chromenone Core: A bicyclic scaffold combining a benzene ring with an α‑pyrone (chromen‑4‑one) system.

• Fluoro Substitution: Two fluorine atoms — one on the chromenone ring (5‑position) and one on the phenyl ring (meta position) — which can influence electronic properties, metabolic stability, and lipophilicity.

• Bromoethyl Side Chain: A 1‑bromoethyl substituent at the 2‑position serves as a reactive handle for further functionalization through nucleophilic substitution and cross‑coupling chemistries.

This combination yields a molecule with distinctive reactivity and physicochemical properties that attract interest for advanced chemical research.

PHYSICAL & CHEMICAL PROPERTIES (TYPICAL/ESTIMATED)

Note: Exact melting point and spectral data (NMR, MS, IR) are available upon request or in supplied documentation.

SYNTHETIC APPLICATIONS & RESEARCH USE

This compound is primarily intended as a research intermediate in synthetic and medicinal chemistry. Its design supports a range of research objectives:

Medicinal Chemistry & Lead Optimization

• Fluorine Effects: Fluorine incorporation is a well‑established strategy to improve metabolic stability and alter biological recognition in drug candidates. Fluoroaryl and fluoroheterocyclic scaffolds are prevalent in modern therapeutic agents.

• Chromenone Derivatives: Chromen‑4‑one moieties are common in bioactive compounds with anticancer, antifungal, anti‑inflammatory, and antioxidant profiles.

• Bromine Handle for Diversification: The reactive bromine substituent enables further derivatization via Suzuki, Heck, or nucleophilic substitution reactions to generate libraries of analogues for structure‑activity relationship (SAR) studies.

Method Development & Synthetic Methodologies

• Cross‑Coupling Studies: The bromoethyl group is valuable for testing or developing nickel, palladium, or copper catalysis for C–C and C–heteroatom bond formation.

• Fluorination Techniques: The presence of multiple fluorinated positions offers opportunities for exploring regioselective transformations and fluorination methodologies.

Agrochemical and Material Science Explorations

While primarily a pharmaceutical intermediate, the chromenone framework and electron‑modulating substituents may support early exploratory research in:

• Agrochemical lead compounds

• Fluorine‑rich materials with unique optical or electronic features

POTENTIAL DERIVATIZATION ROUTES

The 2‑(1‑bromoethyl) substituent enables numerous transformations:

Nucleophilic Substitution

• Reaction with amines to form ethanamines

• Reaction with thiols to generate thioethers

Cross‑Coupling Reactions

• Suzuki–Miyaura coupling with boronic acids/esters

• Heck reactions for C=C bond formation

• Sonogashira coupling with alkynes

These pathways make the compound a flexible precursor for analogue synthesis.

DOCUMENTATION & QUALITY ASSURANCE

ResolveMass Laboratories Inc. provides the following (as applicable):

• Certificate of Analysis (CoA) indicating purity and data

• NMR (¹H/¹³C), MS, and IR spectra

• Safety Data Sheet (SDS)

• Batch tracking and quality control records

Purity specifications and detailed analytical results are available on request or at the time of purchase.

ORDERING INFORMATION

• Packaging: Custom packaging options available

• Purity Grades: Standard and high‑purity options upon request

• Technical Support: Application advice and synthetic route consultation