1-Bromo-4-ethoxy-2-fluorobenzene
[CAS# 107713-66-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ether
• Name: 1-Bromo-4-ethoxy-2-fluorobenzene
• Molecular Formula: C₈H₈BrFO
• Molecular Weight: 219.05
• CAS Registry Number: 107713-66-6
• SMILES: CCOC1=CC(=C(C=C1)Br)F

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.514, Calc.^*
• Boiling Point: 215.3±20.0 ºC (760 mmHg), Calc.^*
• Flash Point: 101.9±6.0 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

1-Bromo-4-ethoxy-2-fluorobenzene is an organic compound belonging to the class of aromatic halogenated ethers, with the molecular structure C8H8BrFO. This compound features a benzene ring substituted with bromine, fluorine, and an ethoxy group, conferring unique chemical reactivity valuable in organic synthesis, particularly in medicinal chemistry and material science. The combination of halogens (bromine and fluorine) in this benzene ring makes 1-Bromo-4-ethoxy-2-fluorobenzene a versatile intermediate for various applications, notably in synthesizing pharmaceuticals, agrochemicals, and specialized organic materials.

The discovery and use of halogenated aromatic compounds like 1-Bromo-4-ethoxy-2-fluorobenzene trace back to the mid-20th century when advances in synthetic organic chemistry enabled the introduction of specific halogens on aromatic rings. The development of selective halogenation methods allowed chemists to explore these compounds for their reactivity, particularly in reactions such as nucleophilic aromatic substitution and palladium-catalyzed cross-coupling. The bromine atom, positioned ortho to the fluorine atom on the benzene ring, renders this compound especially reactive in cross-coupling reactions like Suzuki-Miyaura and Buchwald-Hartwig amination, facilitating its use in constructing complex organic molecules.

In application, 1-Bromo-4-ethoxy-2-fluorobenzene is widely utilized as a precursor in synthesizing biologically active molecules, where its reactivity contributes to building blocks for drugs targeting neurological, inflammatory, and infectious diseases. The bromine and fluorine atoms offer specific interaction sites that can enhance binding affinity in drug-target interactions, making this compound a significant intermediate in drug discovery. Additionally, its fluorine atom provides metabolic stability and lipophilicity, properties advantageous for creating drug candidates with improved pharmacokinetic profiles.

Beyond pharmaceuticals, 1-Bromo-4-ethoxy-2-fluorobenzene also serves as an intermediate in developing materials with unique optical and electronic properties. Aromatic compounds with fluorine substitutions are known to exhibit desirable stability and are applied in synthesizing advanced polymers, dyes, and liquid crystals. These materials are valuable in electronics, where their stability and reactivity under various conditions make them ideal for high-performance applications. Additionally, the ethoxy group on the benzene ring enhances solubility in organic solvents, facilitating easier handling and incorporation into reactions.

The chemical properties of 1-Bromo-4-ethoxy-2-fluorobenzene make it a valuable resource in organic synthesis and various applications. The presence of halogens in the structure not only enhances its reactivity in coupling reactions but also allows for the synthesis of complex molecules used in pharmaceuticals and advanced materials. This compound is a noteworthy example of how halogenated aromatic compounds continue to be integral in research and development across multiple scientific fields.