Ethyl 2-(5-amino-2-bromo-4-fluorophenyl)acetate
[CAS# 1442471-26-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Ethyl 2-(5-amino-2-bromo-4-fluorophenyl)acetate
• Synonyms: ethyl 2-(5-amino-2-bromo-4-fluorophenyl)acetate
• Molecular Formula: C₁₀H₁₁BrFNO₂
• Molecular Weight: 276.10
• CAS Registry Number: 1442471-26-2
• SMILES: CCOC(=O)CC1=CC(=C(C=C1Br)F)N

Properties

• Density: 1.5±0.1 g/cm³ Calc.^*
• Boiling point: 323.4±37.0 ºC 760 mmHg (Calc.)^*
• Flash point: 149.4±26.5 ºC (Calc.)^*
• Index of refraction: 1.561 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

Ethyl 2-(5-amino-2-bromo-4-fluorophenyl)acetate is an aromatic compound featuring a substituted phenyl ring bonded to an ethyl acetate group through a methylene bridge. The phenyl ring bears three substituents: a bromine atom at the 2-position, a fluorine atom at the 4-position, and an amino group at the 5-position. Its molecular formula is C₁₀H₁₁BrFNO₂, and the presence of both electron-withdrawing (bromo and fluoro) and electron-donating (amino) groups on the aromatic ring influences its reactivity and chemical behavior.

This compound is typically synthesized by derivatizing substituted aniline or haloarene precursors. The preparation of the ethyl ester is commonly achieved through esterification or by using ethyl bromoacetate under basic conditions, where the functionalized arylamine acts as a nucleophile. Each of the aryl substituents contributes to the reactivity of the aromatic ring, allowing for controlled synthesis steps leading to the final compound.

Ethyl 2-(5-amino-2-bromo-4-fluorophenyl)acetate has been reported in the literature as a valuable intermediate in medicinal chemistry, particularly in the development of small molecules targeting enzyme inhibition or receptor modulation. Its structural framework enables further derivatization at the amino group, which can be converted into amides, sulfonamides, or ureas. These transformations are essential in creating diverse analogs for structure-activity relationship studies.

The presence of halogen atoms, such as bromine and fluorine, enhances the compound's potential for further functionalization through palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura, Buchwald-Hartwig, and Heck reactions. The bromine at the 2-position is especially reactive in such transformations, making the compound a suitable precursor for the synthesis of more complex aromatic systems. Fluorine substitution on the ring contributes to increased metabolic stability and lipophilicity, characteristics frequently sought in the optimization of pharmaceutical agents.

In research contexts, ethyl 2-(5-amino-2-bromo-4-fluorophenyl)acetate has been utilized in the synthesis of candidate molecules for antitumor, anti-inflammatory, and enzyme-inhibiting properties. These applications rely on the ability to introduce additional chemical groups at specific positions while maintaining the integrity of the phenyl core and ester side chain. The amino group also plays a role in hydrogen bonding interactions when the compound or its derivatives interact with biological targets, an important consideration in drug design.

Outside of pharmaceutical research, the compound may be applied in materials science or chemical biology as a building block. The combination of polar and nonpolar characteristics, along with synthetic flexibility, makes it a useful starting material in the assembly of functional organic molecules.

From a physicochemical standpoint, ethyl 2-(5-amino-2-bromo-4-fluorophenyl)acetate is typically a crystalline solid, soluble in organic solvents such as dichloromethane, ethyl acetate, and dimethylformamide. Its stability under normal laboratory conditions is generally good, though protection from strong acids or bases and prolonged exposure to moisture is advisable to prevent ester hydrolysis or degradation.

Safety data for the compound are limited, but standard precautions applicable to aryl halides and aromatic amines should be followed. These include the use of gloves, protective eyewear, and working in a fume hood to minimize exposure risks. Its brominated and fluorinated structure requires appropriate waste disposal practices consistent with halogenated organic compounds.

Ethyl 2-(5-amino-2-bromo-4-fluorophenyl)acetate serves as a functional intermediate in synthetic organic chemistry, enabling the production of structurally diverse derivatives for research and development in both medicinal and materials science disciplines. Its defined substitution pattern allows for predictable reactivity and broad applicability in constructing complex molecules.

References

2020. Ripretinib. Pharmaceutical Substances, 1.
URL: https://www.thieme.de/en/thieme-chemistry/pharmaceutical-substances-54712.htm