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Ethyl 2-bromovalerate, also known as ethyl 2-bromovalrate, is an important organic compound with the chemical formula C7H13BrO2, a molecular weight of approximately 209.08, CAS 615-83-8, and appears as a colorless liquid at room temperature and pressure. Soluble in organic solvents such as chloroform, ethyl acetate, and methanol, but with relatively low solubility. Its density may vary under different conditions, but typically at room temperature and pressure, its density is about 1.226g/mL (at 25 ° C). This density value causes it to exhibit specific behavior when mixed or separated with other substances, for example, under the action of gravity, it may sink faster than other liquids with lower densities. Can be used in environmental monitoring. Due to its specific chemical properties and structural characteristics, it can serve as an indicator or probe for detecting certain harmful substances or pollutants in the environment. This provides strong support for environmental protection and pollution control.
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Chemical Formula |
C7H13BrO2 |
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Exact Mass |
208.01 |
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Molecular Weight |
209.08 |
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m/z |
208.01 (100.0%), 210.01 (97.3%), 209.01 (7.6%), 211.01 (7.4%) |
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Elemental Analysis |
C, 40.21; H, 6.27; Br, 38.22; O, 15.30 |
Chemical Properties and Physical Characteristics
► Molecular Structure and Formula
Ethyl 2-bromovalerate has the molecular formula C₇H₁₃BrO₂ and a molecular weight of 209.08 g/mol. Its structure consists of a five-carbon chain (pentanoic acid) with a bromine atom substituted at the α-position (carbon-2) and an ethyl ester group (-COOCH₂CH₃) at the carboxyl end. The presence of the electronegative bromine atom and the polar ester group influences its reactivity and solubility.
► Physical State and Appearance
The compound typically appears as a colorless to pale yellow liquid at room temperature. It has a characteristic ester-like odor, though inhalation of its vapors should be avoided due to potential health risks.
► Key Physical Properties
Boiling Point: 190–192°C (lit.)
Density: 1.226 g/mL at 25°C
Refractive Index (n²⁰/D): 1.448
Flash Point: 80.57°C (closed cup)
Solubility: Slightly soluble in chloroform, ethyl acetate, and methanol; insoluble in water.
► Chemical Reactivity
Ethyl 2-bromovalerate is reactive under various conditions:
Nucleophilic Substitution: The bromine atom is susceptible to displacement by nucleophiles (e.g., amines, thiols), making it valuable in synthesizing α-substituted valeric acid derivatives.
Ester Hydrolysis: The ester group can be hydrolyzed under acidic or basic conditions to yield 2-bromovaleric acid and ethanol.
Reduction Reactions: Electrochemical reduction studies in DMF solutions containing Et₄NClO₄ as an electrolyte demonstrate that ethyl 2-bromovalerate can be reduced to products like pentanoic acid ethyl ester (CH₃CH₂CH₂CH₂COOEt) and other derivatives, depending on reaction conditions.
What are the synthetic routes of ethyl 2-bromoisovalerate
Ethyl 2-bromoisovalerate (CAS No. 609-12-1) is synthesized by the following two main routes:
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Synthesis by reaction of ethanol with 2-bromo-3-methylbutyryl bromide: This route uses 2-bromo-3-methylbutyryl bromide as the starting raw material, and esterifies with ethanol to generate the target product. This method is simple, but the preparation of raw material 2-bromo-3-methylbutyryl bromide may involve a complicated process, and the reaction yield is about 60%, which requires further optimization of the conditions to improve the efficiency. |
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Synthesis via bromination of isovaleric acid followed by esterification: This route is carried out in two steps: Step 1: Isovaleric acid (2-methylbutyric acid) is brominated to produce 2-bromo-3-methylbutyric acid. The bromination process requires control of the reaction conditions (e.g., temperature, amount of brominating agent) to avoid over-bromination or generation of by-products. Step 2: Esterification of 2-bromo-3-methylbutyric acid with ethanol to produce ethyl 2-bromoisovalerate. The esterification reaction is usually carried out in the presence of an acidic catalyst (e.g., concentrated sulfuric acid) and yields up to about 82%. This method is easy to obtain raw materials, but there are more steps and the purity of the intermediates needs to be strictly controlled. |
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Other possible synthetic routes: Synthesis of 2-bromoisovaleric acid via DL-valine, followed by esterification to obtain the target product. This route involves chemical conversion of amino acids and may provide an alternative for specific needs, but specific process details need to be further verified. Suggestions for synthetic route selection: If process simplicity is pursued, the direct esterification route of ethanol with 2-bromo-3-methylbutyryl bromide may be evaluated in preference, but feedstock preparation needs to be addressed. If the raw material isovaleric acid is readily available and the yield requirement is high, the two-step method of isovaleric acid bromination followed by esterification is more advantageous. The bromination-esterification route can be used for small-scale synthesis in the laboratory; industrial production requires comprehensive consideration of the cost of raw materials, reaction yield and environmental requirements. |
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Main role in the dyestuffs industry
Ethyl 2-bromoisovalerate is mainly used as synthetic dyes intermediates or functional modifiers in the dyestuff industry, and its applications are reflected in the following aspects:
► Intermediates of synthetic dyes
Introduction of brominated structure: The bromine atom in the molecule of ethyl 2-bromoisovalerate is highly reactive, and can be combined with aromatic amines, phenols or heterocyclic compounds through nucleophilic substitution, coupling reaction, etc. to generate bromine-containing precursors of dyes. For example, in the synthesis of disperse dyes or reactive dyes, the bromine intermediates can be further converted into azo groups, anthraquinone structures or phthalocyanine rings, giving the dyes bright colors and good fastness.
Case in point: some disperse dyes react with p-aminophenol through ethyl bromo isovalerate to generate bromine-containing azo compounds, and then synthesize the final dyestuffs through diazotization, coupling and other steps, which are used for dyeing polyester fibers.
► Functional modifier
Improvement of dyestuff performance: ethyl bromoisovalerate can be used as a side chain modifier to regulate the solubility, dispersibility or binding force of dyestuffs with fibers through the introduction of ester group or bromine atom. For example, in reactive dyestuffs, the brominated side chain enhances the covalent bonding of the dye to the cotton fiber and improves wet treatment fastness.
Case in point: in the synthesis of reactive dyes for cotton, ethyl 2-bromo isovalerate reacts with cyanuric chloride to generate bromine-containing reactive groups, which are then coupled with amino compounds to form dyes with a high affinity for cotton fibers and a good color fixation rate.
► Synthesis of special dyes
Fluorescent dyes: the bromine atom of ethyl bromoisovalerate can enhance the fluorescence quantum yield of dyes through the heavy atom effect, which is used for the synthesis of fluorescent whitening agent or labeling dyes. For example, in the fluorescent whitening of polyester fibers, the bromo intermediate can enhance the luminescence efficiency of the dye.
Light-resistant dyes: Brominated structures absorb UV rays and protect dye molecules from photodegradation, extending the service life of dyes in outdoor applications. For example, in the dyeing of automotive interior fabrics, brominated dyes can maintain long-term color stability.
► Cross-applications with other industries
Pharmaceutical intermediates extension: Ethyl 2-bromoisovalerate, as a by-product or derivative of pharmaceutical intermediates (e.g., synthesis of antibiotics, antiviral drugs), may be converted into dye molecules by structural modification. For example, certain antimicrobial dyes possess both dyeing and antimicrobial functions by introducing fragments of ethyl bromoisovalerate.
Material Science Combination: In the composite of dyes and nanomaterials, ethyl bromoisovalerate can be used as a surface modifier to improve the dispersion of dyes on nanoparticles for the development of smart-responsive dyes or functional textiles.
Main role In the biological industry
In the biological industry, the specific application of ethyl 2-bromoisovalerate is mainly reflected in the field of chiral compound splitting and biocatalysis, and its core value is to achieve efficient and low-cost chiral product synthesis through the biological enzyme technology. The following is the specific application analysis:
► Chiral compound splitting: production of single-configuration products by biocatalytic method
1) Background
Chiral compounds have important applications in the fields of medicine and pesticide, but it is difficult to obtain a single-configuration product by traditional chemical synthesis methods, and it needs to be realized by chiral splitting. 2-Bromoisovaleric acid ethyl ester, as a racemate, can be obtained as a single-configuration product of high purity by bio-enzyme-catalyzed splitting, which can significantly reduce the production cost.
2) Technical Breakthrough
A patent for an invention provides the application of a lipase (amino acid sequence as shown in SEQ ID NO.1) in the splitting of ethyl 2-bromoisovalerate. The lipase is expressed by the genetically engineered bacterium Aspergillus oryzae WZ007 and has the following advantages:
High stereoselectivity: enantiomeric excess value (ee value) of >99%, which results in ethyl (R)-2-bromoisovalerate with very high optical purity.
High conversion: the conversion was 50.8% and the product mass yield was up to 96.4%.
Mild reaction conditions: Splitting can be completed in pH 7.0 buffer at 35℃ and 1000rpm for 5 hours.
3) Application value
Reduce production cost: compared with the traditional chemical splitting method, the bio-enzyme method does not require the use of expensive chiral reagents, and the reaction conditions are mild, with low energy consumption.
Enhancement of economic benefits: high yield and high purity products can be directly used for the synthesis of chiral drugs or pesticides, reducing the number of subsequent purification steps and shortening the production cycle.
► Biocatalysis: Synthesis of chiral drugs and pesticide intermediates
1) Drug Synthesis
Ethyl (R)-2-bromoisovalerate is a key intermediate for the synthesis of cyfluthrin (pyrethroid pesticide). Conventional methods synthesize cyfluthrin via D-valine, but the raw material cost is high. Bio-enzymatic splitting of ethyl 2-bromoisovalerate can provide low-cost chiral raw materials and significantly reduce the production cost of cyfluthrin.
2) Pesticide Intermediates
Cyfluthrin has broad-spectrum insecticidal activity, which can control lepidopteran and coleopteran pests on cotton, fruit trees, vegetables and other crops. Bio-enzymatic splitting technology provides an efficient and environmentally friendly solution for the industrialized production of cyfluthrin, and promotes the green transformation of the pesticide industry.
3) Technical Advantages and Industry Influence
Technical Advantages
Rich source of microorganisms: Lipase can be obtained by fermentation of microorganisms such as bacteria, fungi, etc., which is not restricted by seasonal climate and has a short growth cycle.
High catalytic selectivity: microbial lipase is resistant to organic solvents and has strong substrate specificity, which is suitable for the catalytic reaction of complex substrates.
High value of industrialized application: the expression of recombinant lipase by genetically engineered bacteria can realize large-scale production to meet industrial demand.
Industry Impact
Promote the technological progress of chiral compound synthesis: Bio-enzymatic splitting technology provides a low-cost and high-efficiency solution for chiral drugs and pesticides.
Promote the development of green chemistry: Compared with traditional chemical methods, bio-enzymatic method has mild reaction conditions and reduces the use of toxic reagents, which is in line with the concept of green chemistry.
Products Description
Ethyl 2-bromovalerate is an organic bromide with the chemical formula C₇H₁₃BrO₂ and a molecular weight of 221.08 g/mol. Its appearance is a colorless transparent liquid with a pungent odor, boiling point of 190-192 ℃, and refractive index n ² ⁰/D 1.448. This substance is mainly used as an organic synthesis intermediate for chemical synthesis in the fields of pesticides, pharmaceuticals, and fragrances, such as participating in the synthesis reactions of certain antibiotics and anti-tumor drugs. It has a wide range of industrial applications, but strict adherence to safety operating procedures is required.
Skin and mucosal irritation
Direct contact reaction
Symptoms: Red rashes, edema, and blisters appear at the contact area, and in severe cases, skin necrosis may occur.
Mechanism: Bromide reacts with skin proteins, disrupting cell membrane structure and leading to cytotoxicity.
Inhalation exposure reaction
Symptoms: Nasopharyngeal irritation, cough, difficulty breathing, long-term exposure may cause chemical pneumonia.
Monitoring data: Animal experiments showed that after inhaling 2-bromovalerate ethyl ester vapor (concentration of 500ppm) for 30 minutes, the white blood cell count in the bronchoalveolar lavage fluid of rats significantly increased.
Neurotoxicity
Acute poisoning
Symptoms: Headache, dizziness, fatigue, and in severe cases, blurred consciousness and convulsions may occur.
Dose dependence: Oral doses exceeding 5g may cause central nervous system suppression and even coma.
Chronic exposure effects
Long term risk: Animal experiments have shown that long-term low-dose exposure may lead to neurobehavioral changes, such as decreased motor coordination ability.
Lack of human data: Currently, there are no large-scale epidemiological studies on populations, but potential risks for occupational exposures need to be monitored.
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