Synthesis and Characterization of 5-Bromovaleric Acid
Synthesis and Characterization of 5-Bromovaleric Acid
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5-Bromovaleric Acid: A Key Intermediate in Organic and Pharmaceutical Chemistry
In modern synthetic chemistry, the demand for versatile, functionalized intermediates is ever-growing. One such valuable compound is 5-Bromovaleric Acid, a small yet powerful building block used in the synthesis of pharmaceuticals, fine chemicals, and agrochemical compounds.
Known for its dual functional groups — a bromine atom and a carboxylic acid group — 5-Bromovaleric Acid offers unique reactivity and synthetic flexibility, making it a popular choice in both research and industrial applications.
What Is 5-Bromovaleric Acid?
5-Bromovaleric Acid is a halogenated aliphatic carboxylic acid. Structurally, it is a five-carbon straight-chain molecule with a carboxylic acid (-COOH) at one end and a bromine atom (-Br) at the terminal carbon.
IUPAC Name: 5-Bromopentanoic acid
Molecular Formula: C₅H₉BrO₂
Molecular Weight: 181.03 g/mol
CAS Number: 2067-33-6
Physical Appearance: Colorless to pale yellow liquid or solid (depending on purity and storage conditions)
Solubility: Soluble in water, alcohols, and many organic solvents
This compound is often used as an alkylating agent, a chain extender, or a reactive intermediate in multi-step syntheses.
Chemical Properties and Reactivity
5-Bromovaleric Acid features two highly reactive sites:
The carboxylic acid group can be converted into esters, amides, or acid chlorides for further functionalization.
The bromine atom can undergo nucleophilic substitution, allowing introduction of a wide variety of functional groups like amines, thiols, or azides.
These features allow it to serve as a bridge molecule — ideal for linker synthesis, prodrug development, or surface modification in materials chemistry.
Applications of 5-Bromovaleric Acid
1. Pharmaceutical Intermediate
5-Bromovaleric acid is commonly used in drug development. It acts as a precursor to substituted amino acids, heterocyclic scaffolds, and functionalized chain extenders in complex drug molecules.
It is especially useful for:
Creating linkers in prodrugs and ADCs (antibody-drug conjugates)
Introducing reactive handles in bioactive molecules
Synthesizing small-molecule inhibitors and peptidomimetics
2. Agrochemical Synthesis
Due to its functional flexibility, it is also used in the synthesis of pesticides and herbicides, especially those requiring selective substitution or chain-length specificity.
3. Polymer and Material Science
The reactive bromo-group makes this compound ideal for:
Surface grafting
Click chemistry (azide-alkyne cycloaddition)
Polymer chain initiation or modification
This enables tailored chemical architectures in biomedical devices and functional materials.
Handling and Storage
While relatively stable under ambient conditions, 5-Bromovaleric Acid should be stored away from light and moisture to prevent hydrolysis or degradation.
Handling Tips:
Use gloves and eye protection
Work in a fume hood
Store in tightly sealed containers, preferably under inert atmosphere
Avoid exposure to bases or strong nucleophiles unless intended
It is moderately corrosive and may cause irritation upon contact with skin or eyes.
Availability
5-Bromovaleric Acid is commercially available in both research and bulk quantities from reputable chemical suppliers. It is typically offered at ≥98% purity and shipped in moisture-resistant, amber glass bottles.
Conclusion
5-Bromovaleric Acid is a highly useful intermediate that combines reactivity, versatility, and accessibility. Its unique structure makes it a go-to reagent for applications in drug discovery, materials science, and chemical manufacturing.
Whether you're modifying small molecules, preparing advanced materials, or designing a custom synthesis route, 5-Bromovaleric Acid offers the synthetic power to help you build precisely what you need.
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For those seeking efficient chain-functionalized building blocks, 5-Bromovaleric Acid is a small molecule with big potential.