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Diethyl 2,5-dibromohexanedioate, CAS 869-10-3, molecular formula C10H16Br2O4, usually appears as white crystals or brown solids. Soluble in organic solvents such as alcohols, ethers, and acetone, insoluble in water. Has certain reactivity and can react with various chemical substances. For example, it can undergo esterification reactions with alcohols and substitution reactions with halogens. These reaction properties make them widely applicable in chemical and organic synthesis. It is one of the intermediates for synthesizing polyunsaturated acids. Polyenoic acid is one of the metabolites found in the urine of workers who have been exposed to benzene for a long time, so this compound has certain application value in toxicology and biomedical research.
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Chemical Formula |
C10H16Br2O4 |
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Exact Mass |
357.94 |
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Molecular Weight |
360.04 |
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m/z |
359.94 (100.0%), 357.94 (51.4%), 361.94 (48.6%), 360.94 (9.7%), 362.94 (5.3%), 358.94 (4.4%), 358.94 (1.1%), 360.94 (1.1%) |
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Elemental Analysis |
C, 33.36; H, 4.48; Br, 44.39; O, 17.77 |
Diethyl 2,5-dibromohexanedioate (CAS number: 869-10-3) is an important organic compound that has shown wide application value in multiple fields due to its unique physical and chemical properties.
In the field of medicine, it is mainly reflected in the following aspects:
1. Drug development:
As the starting material or key intermediate for new drug development, it provides an important material basis for the development of new drugs.
By conducting in-depth research on its biological activity and mechanism of action, more new drugs with excellent therapeutic effects and lower toxicity can be developed.
2. Drug metabolism research:
It can also serve as a tool compound for drug metabolism research. By studying its metabolic processes and metabolites in the body, we can understand the mechanisms of drug conversion and excretion in the body.
This helps to evaluate the bioavailability and duration of drug efficacy, providing scientific basis for the clinical application of drugs.
In the field of materials science, applications are mainly reflected in the following aspects:
Composite material modification:
Combining it with inorganic or organic materials can significantly improve the mechanical and heat resistance properties of the composite material.
For example, by combining it with nanomaterials such as graphene and carbon nanotubes, composite materials with high strength, toughness, and conductivity can be prepared.
Environmental Science Field
In the field of environmental science, applications are mainly reflected in the following aspects:
1. Environmental pollutant detection:
Diethyl 2,5-dibromohexanedioate can be used as a reference compound or probe compound for environmental pollutant detection.
By studying its migration, transformation, and ecological effects in the environment, detection methods and standards for environmental pollutants can be established.
This helps to monitor and evaluate the concentration and distribution of environmental pollutants, providing scientific basis for environmental protection and governance.
2. Environmental risk assessment:
By studying its stability and persistence in the environment, potential risks to ecosystems and human health can be assessed.
This helps to formulate scientifically reasonable environmental protection policies and measures, reducing the harm of environmental pollution to humans and ecosystems.
Other fields
In addition to the aforementioned application areas, it has also demonstrated potential application value in other fields:
1. Dye sensitized solar cells:
Can be used as dye molecules or sensitizers in dye-sensitized solar cells.
By optimizing its structure and performance, the photoelectric conversion efficiency and stability of solar cells can be improved.
2. Organic optoelectronic devices:
By utilizing its unique optoelectronic properties, organic optoelectronic devices with excellent optoelectronic performance can be developed.
These devices have broad application prospects in display technology, lighting technology, sensors, and other fields.
3. Analytical Chemistry:
It can also be used as a standard substance or reference substance in analytical chemistry.
By studying its chemical properties and reaction behavior under different conditions, important experimental data and theoretical basis can be provided for analytical chemistry.
In summary, 2,5-dibromohexanedioic acid diethyl ester has shown broad application prospects and potential value in chemical synthesis, pharmaceuticals, pesticides and plant growth regulators, materials science, environmental science, and other fields. With the continuous advancement of science and technology and the deepening of people's understanding of this compound, it is believed that its application fields and potential value will be further expanded and explored. Meanwhile, in the application process, it is also necessary to fully consider issues such as safety and environmental friendliness, and take corresponding measures to reduce risks and hazards.
The oil-water coefficient, also known as LogP value, of 2,5-dibromohexanedioic acid diethyl ester (CAS number: 869-10-3) is an important physical parameter reflecting the distribution of the compound between n-octanol and water phases. However, based on the currently available information, the exact LogP value has not been directly provided. The LogP value is usually obtained through experimental measurements and reflects the distribution tendency of compounds in two different polar solvents. For such organic compounds, the presence of functional groups such as bromine atoms and ester groups in their molecular structure can affect the polarity of the compound, thereby affecting its distribution in n-octanol and water.
It should be noted that due to the fact that LogP values are obtained through experimental measurements and are influenced by various factors such as testing conditions, solvent selection, compound purity, etc., there may be some differences in LogP values from different sources. In practical applications, it is recommended to obtain accurate LogP values through professional experimental measurement methods.
Diethyl 2,5-dibromohexanedioate, as an organic synthesis intermediate, has potential biological activity in drug metabolism research. Although there are few reports on its direct use as a drug, its role in drug metabolism cannot be ignored. The following explores the relationship between its biological activity and drug metabolism from several aspects:
1. Formation of metabolic products
In the process of drug metabolism, drug molecules undergo a series of biotransformation reactions to generate various metabolites. These metabolites may have different biological activity, toxicity, and pharmacokinetic characteristics from the original drug. As metabolites or intermediates of certain drugs, they may participate in these biotransformation processes. For example, among the metabolites found in the urine of workers who have been exposed to benzene for a long time, diethylglutaric acid (dibromoadipic acid) is an intermediate for the synthesis of polyunsaturated acids and may be a key intermediate in this metabolic pathway.
2. Induction and inhibition of two drug metabolizing enzymes
Drug metabolizing enzymes are key enzymes that catalyze drug biotransformation, including cytochrome P450 enzymes, uridine diphosphate glucuronosyltransferase, etc. The activity of these enzymes is influenced by various factors, including drug structure, generation and clearance of metabolites, etc. As a metabolite of certain drugs, it may affect enzyme activity by binding or competing with these enzymes. For example, it may act as a substrate or inhibitor of cytochrome P450 enzymes, altering the metabolic rate and pathways of drugs.
3. Drug interactions
Drug interactions are one of the important aspects in drug metabolism research. It involves the mutual influence of multiple drugs in the body, including induction and inhibition of metabolic enzymes, competition for drug excretion, etc. As a metabolite of certain drugs, it may interact with other drugs. For example, it may affect the metabolism and excretion processes of other drugs by competing for the same metabolic enzymes or excretion channels. This interaction may lead to changes in drug efficacy, increased adverse reactions, or synergistic effects between drugs.
4. Toxicity and Safety Assessment
In the process of drug development, toxicity assessment and safety evaluation are indispensable links. As metabolites of certain drugs, their toxicity characteristics and safety evaluation are of great significance for assessing the toxicity and safety of the entire drug. By studying its toxicity characteristics, the potential toxic effects of drugs in organisms can be predicted, providing important basis for the safety evaluation of drugs. At the same time, by evaluating the toxicity of its metabolites, it is possible to understand the toxic substances that may be produced during drug metabolism, providing guidance for the safe use of drugs.
Stability Research
Chemical Structure and Basic Stability
2, 5-diethyl dibromoadipic acid (C₁₀H₁₆Br₂O₄, molecular weight 360.04 g/mol) is a bromine-containing dicarboxylic acid ester compound. In its molecular structure, the two bromine atoms are located at the 2nd and 5th positions of the adipic acid skeleton, respectively, with ethoxy groups (-OCH₂CH₃) at both ends. This structure endows it with the following stability characteristics:
Thermal stability
The melting point is 65-67°C, the boiling point is 134°C at 0.5 mmHg pressure, and the decomposition temperature at normal pressure is approximately 338.6°C. Debromination or ester bond breakage may occur at high temperatures, but it has good thermal stability under conventional experimental conditions (such as room temperature to 100°C).
Photosensitivity
Sensitive to ultraviolet light. Light exposure may cause bromine atom substitution or ester group photolysis, resulting in color deepening (such as changing from white to light yellow) or the formation of impurities. Store in a brown glass bottle away from light.
REDOX stability
The bromine atom is a strong electron-withdrawing group, making the molecule weakly acidic as a whole. However, it is not easily directly acted upon by common oxidants (such as hydrogen peroxide) or reducing agents (such as sodium thiosulfate), and its stability is superior to that of unbrominated adipates.
The Impact of Environmental Factors on Stability
Temperature
Short-term storage: Stable at room temperature (25°C), but long-term storage requires temperature control. The accelerated stability test (40°C/ 75%RH) showed that after 6 months, the content decreased by approximately 5%, while impurities (such as adipic acid bromide) increased by 2%.
Low-temperature protection: It is recommended to store in a refrigerator at 2-8°C, which can significantly slow down the decomposition rate. Experiments show that under freezing conditions at -20°C, the content loss within one year is less than 1%.
Humidity and Solvents
Hydrolysis risk: Ester bonds are prone to hydrolysis under strong acid or strong base conditions, generating adipic acid and ethanol. The hydrolysis rate is extremely low in a neutral environment, but high humidity (such as RH>80%) may accelerate hygroscopic degradation.
Solvent selection: Readily soluble in organic solvents such as alcohol, ether and acetone, but poorly soluble in water. After dissolving in dichloromethane (DCM), if the solvent contains trace amounts of moisture (such as >0.1%), it may induce slow hydrolysis, and anhydrous solvents should be used.
Oxygen and Packaging
Oxidative degradation: Oxygen may trigger the oxidative side reactions of brominated hydrocarbons, generating brominated peroxides or carboxylic acids. Nitrogen protection can reduce the risk of oxidation and extend the shelf life.
Packaging materials: High-barrier packaging (such as aluminum-plastic composite bags) is superior to ordinary glass bottles and can reduce oxygen penetration. Experiments show that the content retention rate of samples packaged in aluminum-plastic bags (98%) after 12 months is significantly higher than that in glass bottles (92%).
Stability Research Methods
Conditions: 40°C/75% RH, lasting for 6 months.
Detection indicators: content (HPLC), pH value, moisture, appearance (color/sediment).
Result: The content decreased by ≤5%, and the total amount of impurities was ≤2%, which conformed to the ICH stability guideline (Q1A(R2)).
Conditions: 25°C/60% RH, lasting for 24 months.
Testing frequency: Sampling and analysis every six months.
Result: The content decreased by ≤3%, and the total amount of impurities was ≤1.5%, which proved that it had good stability under the recommended storage conditions.
Simulation operation: Simulate scenarios such as bottle opening, portioning, and dilution to detect changes in the content of active ingredients.
Result: The content retention rate is ≥95% when stored at 25°C for no more than 7 days or at 2-8°C for no more than 30 days after opening.
Strategies for Enhancing Stability
Formula optimization
Add antioxidants (such as BHT) or metal ion chelating agents (such as EDTA) to inhibit oxidative degradation.
Adjust the pH to neutral (pH=6-8) to reduce the risk of hydrolysis.
Process control
Sterilization process selection: Avoid high-temperature and high-pressure sterilization. Give priority to aseptic filtration or irradiation sterilization.
Filling environment: Fill under nitrogen protection to reduce oxygen residue.
Storage and Transportation
Short-term storage: Refrigerate at 2-8°C, avoid freezing.
Long-term storage: Freeze at -20° C. Aliquot into small doses to minimize repeated freeze-thaw cycles.
Transportation conditions: Transport in a dark place below 25°C and avoid severe vibration.
Frequently Asked Questions
Q: Why does diethyl 2,5‑dibromohexanedioate often show partial racemization during storage?
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A: The molecule has two chiral centers at C2 and C5. Under weak base or heat, the α‑bromo ester can undergo reversible deprotonation to form an enolate intermediate, which leads to partial epimerization and racemization over time, especially in non‑anhydrous conditions.
Q: Can this compound undergo intramolecular cyclization under basic conditions? If so, what product forms?
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A: Yes. Under strong base (e.g., NaOEt, NaH), intramolecular SN2 displacement can occur between one bromide and the enolate of the other ester, forming a substituted cyclopropane‑1,2‑dicarboxylate derivative via ring closure.
Q: Why is it difficult to reduce only one bromo group selectively in diethyl 2,5‑dibromohexanedioate?
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A: The two bromine atoms are structurally equivalent and electronically similar. Most reducing agents (Zn, Mg, H₂/Pd, etc.) cannot distinguish them well, leading to either both bromines reduced or mixtures of mono‑ and dibromo products rather than clean monoreduction.
Q: Does this dibromo ester show significant sensitivity to light? What changes occur?
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A: Yes. Prolonged light exposure promotes homolytic cleavage of C–Br bonds, generating alkyl radicals. These can undergo elimination, dimerization, or oxidation, resulting in color darkening, formation of unsaturated esters, and reduced purity.
Q: Why is aqueous extraction purification of this compound often inefficient?
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A: Although it is an ester, its dibromo structure increases molecular weight and lipophilicity significantly. It partitions strongly into organic phases and shows very low solubility in water, so aqueous washing does not effectively remove polar impurities; column or distillation is usually required.
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