5-Bromo valeric acid, also known as 5-bromopentanoic acid, is an organic compound classified as a halogenated carboxylic acid. It features a five-carbon chain (valeric acid) with a bromine atom attached to the fifth carbon. This compound is notable for its utility in various chemical syntheses, serving as an intermediate for pharmaceuticals, agrochemicals, and other fine chemicals.
Chemical Structure and Properties
Chemical Name: 5-Bromo valeric acid
Molecular Formula: C₅H₉BrO₂
Molecular Weight: 181.03 g/mol
CAS Number: 2067-33-6
Physical Properties:
| Property | Description |
|---|---|
| Appearance | Colorless to pale yellow liquid |
| Melting Point | -9°C |
| Boiling Point | 221-223°C |
| Density | 1.539 g/cm³ |
| Solubility in Water | Slightly soluble |
| Solubility in Organic Solvents | Soluble in most organic solvents such as ethanol, ether, and chloroform |
The structure of 5-bromo valeric acid consists of a valeric acid backbone with a bromine substituent at the terminal carbon (fifth carbon). The presence of the bromine atom significantly impacts the compound’s reactivity and polarity, making it useful in various chemical reactions.
Synthesis
5-Bromo valeric acid can be synthesized through several methods. The most common method involves the bromination of valeric acid. This process is typically carried out under controlled conditions using a brominating agent such as phosphorus tribromide (PBr₃) or bromine (Br₂) in the presence of a solvent like acetic acid or dichloromethane. The reaction is carefully monitored to ensure selective bromination at the terminal carbon.
Another synthesis route involves the Grignard reaction, where a Grignard reagent (such as pentyl magnesium bromide) reacts with carbon dioxide to form 5-bromo valeric acid. This method provides good yields and is suitable for producing 5-bromo valeric acid on a larger scale.
Applications
5-Bromo valeric acid serves as an important intermediate in the synthesis of various organic compounds across multiple industries:
- Pharmaceuticals: In the pharmaceutical industry, 5-bromo valeric acid is used as a building block for synthesizing active pharmaceutical ingredients (APIs) and intermediates. It plays a role in creating molecules that may have anti-inflammatory, analgesic, or antiviral properties.
- Agrochemicals: This compound is also valuable in the agrochemical industry for producing herbicides, fungicides, and insecticides. The bromine atom enhances the bioactivity and stability of these agrochemical products, making them more effective in agricultural applications.
- Organic Synthesis: In organic chemistry, 5-bromo valeric acid is utilized as a reagent in various chemical transformations. It is often employed in the synthesis of esters, amides, and other derivatives, which can be further modified to create complex molecules.
- Material Science: In material science, 5-bromo valeric acid can be used to synthesize novel polymers and materials with specific properties. The bromine atom introduces functional groups that can be exploited for cross-linking and other chemical modifications.
Safety and Handling
Handling 5-bromo valeric acid requires caution due to its potential hazards. It can cause irritation to the skin, eyes, and respiratory system upon contact. Inhalation of vapors may result in respiratory tract irritation. Therefore, appropriate personal protective equipment (PPE), such as gloves, safety goggles, and lab coats, should be worn when working with this compound.
In case of accidental exposure, affected areas should be thoroughly washed with water, and medical attention should be sought if irritation persists. It is also important to handle 5-bromo valeric acid in a well-ventilated area or under a fume hood to minimize inhalation risks.
Environmental Impact
5-Bromo valeric acid can pose environmental hazards if not disposed of properly. It is considered toxic to aquatic life and can cause long-term adverse effects in aquatic environments. As such, waste containing 5-bromo valeric acid should be disposed of following local regulations and environmental guidelines to prevent contamination of water bodies and soil.
Conclusion
5-Bromo valeric acid is a versatile compound with significant applications in pharmaceuticals, agrochemicals, and organic synthesis. Its unique chemical properties, due to the presence of the bromine atom, make it a valuable intermediate for various chemical processes. However, due to its potential hazards, proper handling and disposal practices are essential to minimize health risks and environmental impact.
FAQ
5-Bromovaleric acid is used in the synthesis of inhibitors for aminoglycoside resistant bacteria.
Valeric acid, and its esters, is mainly used in perfumes and cosmetics, as food additives because of the fruity flavor of the esters, and as plasticizers and pharmaceuticals.
3 What is the preparation of valeric acid?
Manufacture. In industry, valeric acid is produced by the oxo process from 1-butene and syngas, forming valeraldehyde, which is oxidised to the final product.
Salicylic acid is the most common BHA found in skin care products. “BHAs like salicylic acid get really deep into the pores, whereas the water-soluble ones don’t go as deep,”
