Methyl 2-bromo-4,5-difluorobenzoate
[CAS# 878207-28-4]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorobenzoic acid series
• Name: Methyl 2-bromo-4,5-difluorobenzoate
• Molecular Formula: C₈H₅BrF₂O₂
• Molecular Weight: 251.02
• CAS Registry Number: 878207-28-4
• SMILES: COC(=O)C1=CC(=C(C=C1Br)F)F

Properties

• Density: 1.7±0.1 g/cm³ Calc.^*
• Boiling point: 249.5±40.0 ºC 760 mmHg (Calc.)^*
• Flash point: 104.7±27.3 ºC (Calc.)^*
• Index of refraction: 1.514 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

Methyl 2-bromo-4,5-difluorobenzoate is an aromatic ester characterized by a benzene ring substituted with a bromine atom at the 2-position, fluorine atoms at the 4- and 5-positions, and a methyl ester group at the 1-position. The presence of multiple halogen atoms along with the ester function provides the molecule with distinctive reactivity and electronic properties, making it valuable as a synthetic intermediate.

The discovery of methyl 2-bromo-4,5-difluorobenzoate is rooted in the systematic exploration of halogenated aromatic compounds during the mid-20th century. During this period, chemists were intensively investigating how halogen substitution affected the reactivity and stability of aromatic molecules. The introduction of fluorine atoms, known for their high electronegativity and small atomic radius, was particularly important for modulating the electron density of the aromatic ring. In combination with bromine, which serves as an excellent leaving group in cross-coupling reactions, this substitution pattern was found to be especially useful for fine-tuning chemical reactivity in synthetic processes.

Applications of methyl 2-bromo-4,5-difluorobenzoate are mainly focused on its role as a precursor in organic synthesis. The bromine atom enables various palladium-catalyzed cross-coupling reactions, such as Suzuki-Miyaura, Heck, and Sonogashira couplings, facilitating the construction of more complex aromatic and heteroaromatic structures. The difluoro substitution pattern significantly influences the electronic properties of the molecule, often enhancing the chemical stability and modifying the reactivity of the resulting products.

In pharmaceutical chemistry, compounds derived from methyl 2-bromo-4,5-difluorobenzoate have been used to build fluorinated frameworks, which are highly desirable in drug discovery. Fluorine atoms can improve the bioavailability, metabolic stability, and binding affinity of drug candidates. Therefore, intermediates like methyl 2-bromo-4,5-difluorobenzoate serve as important building blocks for synthesizing biologically active molecules, particularly in the development of kinase inhibitors, antiviral agents, and anti-inflammatory compounds.

In the field of agrochemicals, fluorinated aromatic esters are often employed to create herbicides and insecticides with improved potency and environmental stability. Methyl 2-bromo-4,5-difluorobenzoate provides a versatile platform for modifying the molecular structures of these bioactive compounds, often contributing to the fine-tuning of their physicochemical properties such as lipophilicity and resistance to metabolic degradation.

Materials science also benefits from this compound, particularly in the synthesis of specialty polymers and advanced materials where fluorinated aromatics are required. The incorporation of difluorinated aromatic rings can impart unique characteristics such as enhanced thermal stability, chemical inertness, and altered surface energies, which are critical for the development of high-performance coatings, membranes, and electronic materials.

Additionally, the ester functional group of methyl 2-bromo-4,5-difluorobenzoate can undergo straightforward transformations, including hydrolysis to the corresponding carboxylic acid or conversion to amides and other derivatives. These reactions expand the utility of the compound in constructing diverse chemical architectures.

In summary, methyl 2-bromo-4,5-difluorobenzoate is a key intermediate that exemplifies the strategic use of halogenated aromatic esters in modern synthetic chemistry. Its discovery is part of the broader effort to understand and exploit the chemical behavior of multi-halogenated aromatics, leading to significant applications across pharmaceuticals, agrochemicals, and materials science.