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Ethyl bromopyruvate, also known as 3-bromopyruvate ethyl ester, is a highly reactive organic compound widely used in chemical synthesis and pharmaceutical research. Under normal conditions, it appears as a colorless to pale yellow liquid with a distinct pungent, chili‑like odor, which serves as a notable sensory characteristic.
Due to the high reactivity of its carbon‑bromine bond, ethyl bromopyruvate acts as a strong C–Br activator and is frequently employed as an effective brominating agent in various organic transformations. In terms of solubility, this compound is insoluble in water, but shows good compatibility with many common organic solvents, including ethanol, diethyl ether, and other aprotic solvents.
In organic synthesis, ethyl bromopyruvate is a versatile building block with broad applications. It is widely utilized as a key reagent in esterification, halogenation, and other substitution or condensation reactions. Moreover, it plays an important role in heterocyclic chemistry, such as in the preparation of thiazole derivatives through reactions involving primary amines and carbon disulfide. Beyond synthetic chemistry, it also serves as a valuable pharmaceutical intermediate for the manufacture of medicinally active compounds.
Ethyl bromopyruvate poses certain safety risks. It is irritating to tissues and exhibits mild anesthetic effects. Direct contact with the skin or eyes may cause severe irritation, inflammation, or even chemical burns. Therefore, proper protective equipment, including safety goggles and chemical‑resistant gloves, must be worn during handling. Operations should be performed in a well‑ventilated area to prevent inhalation of harmful vapors. In case of accidental ingestion or inhalation, immediate medical attention is strongly recommended.
For storage and transportation, ethyl bromopyruvate must be isolated from flammable materials and oxidizing agents to avoid hazardous reactions. Containers should be kept tightly sealed, and the product stored in a cool, secure place away from ignition sources and high temperatures to ensure stability and safety.
Additional information of chemical compound:
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Chemical Formula |
C5H7BrO3 |
|
Exact Mass |
193.96 |
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Molecular Weight |
195.01 |
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m/z |
193.96(100.0%),195.96(97.3%),194.96(5.4%),196.96(5.3%) |
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Elemental Analysis |
C, 30.80; H, 3.62; Br, 40.97; O, 24.61 |
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Boiling point |
98-100℃10 mm Hg(lit.) |
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Density |
1.554 g/mL at 25℃(lit.) |
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Storage conditions |
2-8℃ |
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Ethyl Bromopyruvate is an important organic compound widely used in the fields of medicine, agriculture, chemical engineering, and scientific research. Its unique chemical properties and multifunctionality make it a key component in many studies and applications. The following are its specific applications in multiple fields:
This substance exhibits significant potential in anti-cancer drug research. Research has shown that it can block the energy supply of cancer cells and lead to cancer cell apoptosis by inhibiting key enzymes in the glycolytic pathway, such as hexokinase II. This mechanism makes it a potential anti-cancer agent, particularly demonstrating unique advantages in combating drug-resistant cancer cells. For example, a study found that it can effectively inhibit the growth of a variety of cancer cells, including lung cancer, breast cancer and colon cancer cells.
In addition, it has been used to develop targeted drug delivery systems by combining them with nanocarriers to improve drug targeting and efficacy, while reducing toxic side effects on normal cells. It has also shown promising application prospects in the development of antibacterial agents. Its potent antibacterial activity is mainly attributed to its ability to interfere with bacterial metabolic pathways, particularly glycolysis and the tricarboxylic acid cycle.
Research has shown that it has significant inhibitory effects on various drug-resistant bacteria, such as Staphylococcus aureus and Escherichia coli. For example, a study showed that it can effectively inhibit the growth of drug-resistant Staphylococcus aureus, and its antibacterial effect is superior to some traditional antibiotics.In addition, it has been used to develop new antibacterial coatings and dressings for the prevention and treatment of wound infections. These applications not only enhance the effectiveness of antimicrobial agents, but also reduce the misuse of antibiotics and the development of resistance.
The application of this substance in the pharmaceutical field is not limited to anti-cancer and antibacterial, but has also been explored for the treatment of other diseases such as inflammation and metabolic disorders. For example, studies have shown that it can have potential anti-inflammatory effects by inhibiting the release of inflammatory mediators and reducing inflammatory responses. In addition, it is also used to study its application in metabolic diseases, such as diabetes and obesity, and improve the metabolic status of patients by regulating metabolic pathways.
The application of Ethyl Bromopyruvate in agriculture mainly focuses on pesticides and plant growth regulators. Its unique chemical properties and biological activity make it an important tool for increasing crop yield and preventing pests and diseases. It has shown great potential in pesticide development. Its strong antibacterial and antifungal activity makes it an ideal choice for preventing and controlling crop diseases. Research has shown that this substance can effectively inhibit the growth of various plant pathogens, such as gray mold, rice blast fungus, and anthracnose fungus. For example, a study found that it has a significant inhibitory effect on gray mold, and its mechanism of action is to interfere with the metabolic pathways of the pathogen, leading to its death.
In addition, it has been used to develop new pesticide formulations by combining them with nanocarriers to improve the stability and targeting of pesticides, thereby reducing pesticide use and environmental residues. It also shows good application prospects in plant growth regulators. It can promote plant growth and increase crop yield by regulating metabolic pathways within the plant body. Research has shown that it can improve the efficiency of photosynthesis in plants, enhance nutrient absorption and utilization capabilities, thereby promoting plant growth and development.
For example, a study found that rice plants treated with the substance showed significantly better growth rate and yield than the untreated control group. In addition, it has been used to study its application under adverse conditions such as drought and salt stress, by regulating the physiological metabolism of plants and improving their stress resistance and adaptability. The application of this substance in the agricultural field is not limited to pesticides and plant growth regulators, but has also been explored for other purposes such as seed treatment and soil improvement.
Studies have shown that it can improve the germination rate of seeds and the robustness of seedlings by processing them, laying the foundation for high and stable crop yields. In addition, it has been used to study its application in regulating soil microbial communities, by inhibiting the growth of harmful microorganisms and promoting the reproduction of beneficial microorganisms, thereby improving the soil ecological environment.
The application of this substance in the chemical industry is mainly reflected in its important role as an organic synthesis intermediate and a polymer material additive. Its unique chemical structure and reactivity enable it to play a critical role in various chemical processes. It is widely used as an organic synthesis intermediate in the synthesis of various complex organic compounds. Due to the presence of active bromine atoms and ester groups in its molecules.
It can participate in various nucleophilic substitution reactions and ester exchange reactions, providing convenience for the synthesis of various organic compounds.For example, in drug synthesis, it is commonly used to prepare molecules with biological activity, such as anticancer drugs and antibacterial agents. In addition, it can also be used for synthesizing fine chemicals such as fragrances and dyes. Through its reactivity, specific functional groups can be efficiently introduced to obtain the desired chemical properties. It also shows significant application potential in the field of polymer material additives.
04.Application in the field of chemical engineering
Ethyl Bromopyruvate can be used as a crosslinking agent or modifier to improve the properties of polymer materials. For example, in polymer synthesis, it can form cross-linked structures by reacting its active bromine atoms with functional groups on the polymer chain, thereby improving the mechanical strength and thermal stability of the material. In addition, it can also be used as a flame retardant and added to polymer materials to suppress the combustion process through its decomposition products, thereby improving the flame retardant performance of the material.
Industrial Applications
► Pharmaceutical Intermediate
Ethyl bromopyruvate is a key intermediate in the synthesis of Xindanjing, a cardioactive drug used to treat arrhythmias. Its α-bromo carbonyl group enables coupling reactions with nucleophiles, facilitating the construction of complex molecular frameworks.
► Anticancer Agent Development
The compound's reactivity makes it valuable in the synthesis of bromopyruvate analogs, which have shown promise as inhibitors of glycolytic enzymes (e.g., hexokinase II) in cancer cells. These analogs disrupt energy metabolism, leading to cell death in tumor tissues.
► Enzyme Inhibitors
Ethyl bromopyruvate is used to synthesize inhibitors of pyruvate dehydrogenase kinase (PDK) and other metabolic enzymes. These inhibitors are studied for their potential in treating metabolic disorders and neurodegenerative diseases.
► Organic Synthesis
The compound serves as a versatile reagent in:
Alkylation Reactions: The α-bromo group undergoes nucleophilic substitution with amines, thiols, and alcohols.
Cross-Coupling Reactions: Pd-catalyzed couplings with boronic acids or stannanes yield aryl- or vinyl-substituted pyruvates.
Heterocycle Synthesis: It is used to construct thiazolidines, oxazoles, and other nitrogen-containing heterocycles via cyclization reactions.
adverse reaction
Ethyl Bromopyruvate (CAS number 70-23-5, chemical name 3-bromo-2-oxopropionic acid ethyl ester) is a bromine containing organic compound commonly used in organic synthesis and biochemical research. Its molecular formula is C ₅ H ₇ BrO3, with a molecular weight of 191.01 g/mol. It appears as a colorless to pale yellow liquid with a pungent odor. As a laboratory reagent, it may enter the human body through skin contact, inhalation, or ingestion, causing adverse reactions.
Skin: Contact may cause redness, swelling, itching, or burning sensation. Long term or repeated contact may lead to dryness, cracking, or contact dermatitis of the skin.
Eyes: Splashing into the eyes can cause severe pain, tearing, photophobia, conjunctival congestion, and in severe cases, may lead to corneal epithelial damage or temporary blurred vision.
Mucosa: Inhalation of vapors or aerosols may irritate the mucous membranes of the nasal cavity, throat, and respiratory tract, resulting in coughing, sneezing, runny nose, or difficulty breathing. Its irritability stems from the bromine atoms and carbonyl groups in its chemical structure. Bromine atoms have high reactivity and can react with proteins and lipids in the skin or mucous membranes, disrupting the integrity of cell membranes; Carbonyl groups may exacerbate tissue damage through oxidative stress reactions. In addition, its lipophilic properties make it easy to penetrate the skin barrier, increasing the risk of systemic absorption.
Chronic exposure: Long term exposure to low concentrations may lead to chronic bronchitis, decreased lung function, or airway hyperresponsiveness.Respiratory irritation is mainly caused by compounds directly acting on airway epithelial cells. Decomposition products such as hydrogen bromide can disrupt the ciliary clearance function of the airway, leading to inflammatory cell infiltration and airway remodeling. In addition, systemically absorbed compounds may affect the lungs through blood circulation, inducing or exacerbating lung diseases.
Acute exposure: Upon inhalation of high concentrations of vapors or aerosols, symptoms of nasopharyngeal irritation such as coughing, chest tightness, shortness of breath, or wheezing may immediately occur.
Special risk: Under high temperature conditions (such as heating or combustion), Ethyl Bromopyruvate may decompose to produce hydrogen bromide (HBr), further exacerbating respiratory damage.
Oral ingestion: Ingestion may cause burning pain in the mouth, throat, and esophagus, accompanied by nausea, vomiting, abdominal pain, or diarrhea. Severe cases may result in gastrointestinal bleeding or perforation.
Inhalation intake: Long term inhalation of vapors may cause decreased appetite, weight loss, or malnutrition.
The digestive system reaction is mainly caused by the direct corrosive effect of compounds. Bromine atoms and carbonyl groups can disrupt the gastrointestinal mucosal barrier, leading to local inflammation and ulcer formation. In addition, systemically absorbed compounds may affect liver metabolic function, but existing data does not show significant hepatotoxicity.
Oral LD ₅₀: unclear, but based on toxicity data of similar structural compounds (such as bromoacetate), it is speculated that its acute oral toxicity is low (LD ₅₀>2000 mg/kg).
Skin absorption: Long term exposure may cause compounds to enter the bloodstream through the skin, triggering systemic reactions such as headaches, dizziness, or fatigue.
Carcinogenicity: Not classified as a carcinogen by IARC, NTP, or ACGIH.
Reproductive toxicity: There is insufficient evidence to suggest that it has reproductive or developmental toxicity, but pregnant and lactating women should avoid contact.
Neurotoxicity: Long term exposure may lead to central nervous system suppression, manifested as drowsiness, lack of concentration, or memory loss.
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