2-(4-Bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl)acetic acid
[CAS# 1007572-07-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 2-(4-Bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl)acetic acid
• Molecular Formula: C₁₅H₈BrClFNO₃
• Molecular Weight: 384.58
• CAS Registry Number: 1007572-07-7
• SMILES: C1=CC(=C(C(=C1CC(=O)O)F)OC2=CC(=CC(=C2)C#N)Cl)Br

Properties

• Density: 1.7±0.1 g/cm³ Calc.^*
• Boiling point: 453.2±45.0 ºC 760 mmHg (Calc.)^*
• Flash point: 227.9±28.7 ºC (Calc.)^*
• Index of refraction: 1.655 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P280-P305+P351+P338

Discovory and Applicatios

2-(4-Bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl)acetic acid is a substituted phenylacetic acid derivative that incorporates multiple halogens and a cyano group, contributing to its utility as a synthetic intermediate in medicinal and agrochemical chemistry. The compound’s structure is defined by a central acetic acid moiety linked to a tri-substituted phenyl ring bearing bromine and fluorine substituents and connected through an ether linkage to a second phenyl ring substituted with chlorine and a nitrile group.

The molecular framework of this compound combines electron-withdrawing groups such as bromine, fluorine, chlorine, and cyano (–CN) on a biphenyl ether backbone, which confers unique electronic properties. These features influence both reactivity and biological interaction potential. The cyano group on the second phenyl ring is a key functional handle that allows further chemical modification or acts as a hydrogen bond acceptor in receptor binding. The fluorine and bromine atoms offer sites for potential halogen bonding interactions and improve metabolic stability, while also affecting the compound’s lipophilicity and membrane permeability.

The synthesis of 2-(4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl)acetic acid generally proceeds through a multi-step strategy. The approach typically involves the formation of the ether bond between the two aromatic rings via nucleophilic aromatic substitution. In this step, a phenol derivative—such as 3-chloro-5-cyanophenol—reacts with an appropriately halogenated fluorobromophenyl derivative. This is followed by functionalization of the side chain to introduce the acetic acid group, often via halogen-lithium exchange and carboxylation or through alkylation with a halogenated acetic acid derivative. The regioselective introduction of each substituent is based on well-established principles of electrophilic and nucleophilic aromatic substitution and is supported by multiple synthetic methodologies reported in the literature.

This compound has been investigated primarily for its role as an intermediate in the synthesis of more complex pharmacologically active molecules. The substituted phenylacetic acid core is a structural motif found in various nonsteroidal anti-inflammatory drugs, herbicides, and enzyme inhibitors. The electron-deficient aromatic system in this case enhances potential binding affinity in hydrophobic and polar pockets of enzyme active sites or receptor domains.

Compounds of this structural class are often evaluated for activity against targets such as kinases, nuclear hormone receptors, or enzymes involved in lipid metabolism, although 2-(4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl)acetic acid itself is not currently known to be marketed as an active pharmaceutical ingredient. Nevertheless, the compound’s profile fits within a class of synthetic intermediates used in structure-activity relationship studies during early-phase drug discovery.

From a physicochemical perspective, the molecule is expected to be a crystalline solid with moderate to low aqueous solubility due to the presence of multiple aromatic rings and halogen atoms. It is soluble in common organic solvents such as dimethylformamide, tetrahydrofuran, and dichloromethane. The presence of the carboxylic acid group allows for salt formation, improving its handling and solubility in certain formulations when needed.

Proper laboratory handling is essential, particularly because of the halogenated aromatic groups and the nitrile moiety, which may present toxicological risks upon prolonged exposure. Standard safety precautions should include working in a fume hood, wearing gloves, eye protection, and avoiding skin contact or inhalation of dust or vapors.

In summary, 2-(4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl)acetic acid is a chemically stable, functionally diverse synthetic intermediate valued for its modularity and suitability for further chemical elaboration. Its structure supports its use in the synthesis of novel compounds intended for pharmaceutical and agrochemical development, especially in areas where halogenated aromatic systems and cyano functionalities are essential for activity.