Reactivity Profile of 5-Bromovaleric Acid in Substitution Reactions
Reactivity Profile of 5-Bromovaleric Acid in Substitution Reactions
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5-Bromovaleric Acid: A Versatile Intermediate in Organic and Pharmaceutical Chemistry
In the toolbox of synthetic chemistry, certain molecules serve as key intermediates across a wide range of industries. 5-Bromovaleric Acid, also known as 5-bromopentanoic acid, is one such compound — combining a reactive halogen with a carboxylic acid to offer exceptional versatility in both small-scale laboratory synthesis and industrial manufacturing.
What Is 5-Bromovaleric Acid?
5-Bromovaleric Acid is a straight-chain, five-carbon molecule containing two reactive functional groups:
A carboxylic acid (-COOH) at one end
A bromine atom (-Br) at the terminal carbon
This dual functionality allows for nucleophilic substitution reactions at the bromine and derivatization at the carboxylic acid, making it highly adaptable for a variety of synthetic pathways.
Key Chemical Properties
Here is a summary of the essential chemical and physical characteristics of 5-Bromovalaric acid
| Property | Details |
|---|---|
| IUPAC Name | 5-Bromopentanoic acid |
| Molecular Formula | C₅H₉BrO₂ |
| Molecular Weight | 181.03 g/mol |
| CAS Number | 2067-33-6 |
| Appearance | Colorless to pale yellow liquid |
| Functional Groups | Carboxylic acid, alkyl bromide |
| Solubility | Soluble in water and alcohols |
| Density (approx.) | 1.5 g/cm³ |
| Boiling Point | ~255 °C (may decompose) |
| Flash Point | >110 °C |
| Storage Conditions | Cool, dry place; airtight bottle |
Applications of 5-Bromovaleric Acid
1. Pharmaceutical Synthesis
Used as a linker or building block in drug discovery and active pharmaceutical ingredient (API) development. The bromine can be substituted by nucleophiles like amines or azides, while the carboxylic acid allows for easy derivatization to esters or amides.
2. Agrochemicals
An intermediate for selective pesticides and herbicides, where molecular precision is required. Enables the development of functional molecules with tailored activity and environmental behavior.
3. Polymers and Advanced Materials
Acts as a functional monomer or surface modifier. Enables grafting, cross-linking, and custom functional group installation in advanced polymer systems.
Example Reaction: Synthesis of 5-Azidovaleric Acid
One classic transformation involves replacing the bromine atom with an azide group to form 5-azidovaleric acid, which can then be used in click chemistry applications (e.g., in drug delivery systems or bioconjugation).
Reaction Scheme:
5-Bromovaleric Acid + NaN₃ → 5-Azidovaleric Acid + NaBr
Reagents: Sodium azide (NaN₃), DMF (solvent)
Conditions: 60–80 °C, 6–12 hours
Mechanism: SN2 substitution of bromine with azide
Product Use: Can be further reacted with alkynes via CuAAC ("click") to form 1,2,3-triazoles — a key motif in drug discovery and materials science.
Handling and Safety Notes
Although 5-Bromovaleric Acid is relatively stable, it should be handled with appropriate safety precautions:
Use gloves and goggles during handling.
Avoid contact with skin and eyes; vapors may be irritating.
Store in a cool, dry, well-ventilated place.
Keep container tightly closed to prevent moisture absorption or decomposition.
Conclusion
5-Bromovaleric Acid is a compact yet highly reactive molecule that serves as a cornerstone intermediate in synthetic chemistry. Whether you’re designing pharmaceuticals, developing advanced materials, or creating new agrochemicals, its dual functionality offers unmatched versatility and control.
With the ability to participate in both substitution and condensation reactions, it provides chemists with the synthetic flexibility needed for modern, efficient molecular construction.
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For research, development, or production-scale chemistry, 5-Bromovaleric Acid is a proven, reliable, and accessible building block — ready to support your next innovation.