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2-Bromomalonaldehyde , also known as bromomalondialdehyde or bromomalealdehyde, is an important organic compound. The appearance is usually a pale yellow solid or colorless to pale yellow liquid, which can dissolve in water and is also soluble in organic solvents such as alcohols, ethers, acetonitrile, and DMSO (slightly soluble). When heated, it will decompose and may produce toxic gas hydrogen bromide. This compound is the main intermediate for the synthesis of heterocyclic compounds such as pyrimidine and imidazole, widely used in the synthesis of liquid crystals and some raw materials for drug synthesis. It can also be used to prepare intermediate compounds such as Lometrexed. Therefore, it should be stored tightly in a cool and dry place, avoiding contact with oxidants, acids, and other flammable substances to prevent dangerous reactions or fires.
Additional information of chemical compound:
|
Chemical Formula |
C3H3BrO2 |
|
Exact Mass |
149.93 |
|
Molecular Weight |
150.96 |
|
m/z |
149.93(100.0%),151.93(97.3%),150.93(3.2%),152.93(3.2%) |
|
Elemental Analysis |
C, 23.87; H, 2.00; Br, 52.93; O, 21.20 |
|
Melting point |
132-136℃(lit.) |
|
Boiling point |
134.8±25.0℃(Predicted) |
|
Density |
1.750±0.06 g/cm3(Predicted) |
|
Storage conditions |
under -20℃ |
|
|
|
2-Bromomalonaldehyde, also known as bromomalondialdehyde, is an important organic compound with a wide range of applications in various fields. The following is a detailed explanation of its purpose:
1,4-Dihydroquinoline is a class of biologically active compounds widely present in natural products and pharmaceuticals. 2-bromomalondialdehyde can be used to construct the structure of 1,4-dihydroquinoline. Its C-3 chiral sulfoxide group can serve as a cyclic NADH model, participating in the asymmetric reduction reaction of methyl benzoate to generate methyl phenylethanoate. This reaction process not only provides a new method for the synthesis of 1,4-dihydroquinoline, but also offers new ideas for the development of related drugs.
Acetaldehyde is an important chemical raw material widely used in fields such as dyes, fragrances, and pharmaceuticals. 2-bromomalondialdehyde can react with substituted guanine to form glyoxal derived adducts. These adducts are of great significance in drug synthesis and biological activity research. Acetaldehyde derived adducts can serve as important intermediates for the synthesis of new drugs. By studying its structure and properties, we can gain a deeper understanding of the mechanisms and laws of related chemical reactions, providing a theoretical basis for the development of new drugs.
Meanwhile, these adducts may also have direct pharmacological activity, providing new candidate compounds for new drug development. In addition to the above-mentioned uses, 2-bromomalondialdehyde can also participate in the synthesis process of other drugs. For example, it can be used as one of the raw materials for synthesizing certain anti-tumor drugs.
The raw materials of 2-bromomalondialdehyde are widely available and can be prepared by various methods. This makes it have great potential for application in the field of pharmaceutical intermediates. The chemical reaction conditions involving 2-bromomalondialdehyde are relatively mild and do not require extreme conditions such as high temperature and high pressure. This is beneficial for reducing production costs and improving production efficiency. By appropriate separation and purification methods, high-purity 2-bromomalondialdehyde and its derivatives can be obtained. This helps to ensure the quality and safety of the medication. 2-bromomalondialdehyde and its derivatives have diverse pharmacological activities and can be used to treat various diseases. This provides more choices and possibilities for new drug development.
Environmentally friendly applications
With the increasing awareness of environmental protection, the application of environmentally friendly compounds is receiving more and more attention from people. 2-bromomalondialdehyde, as an organic compound, has potential value in certain environmentally friendly applications due to its structural characteristics. For example, 2-bromomalondialdehyde can be used as one of the synthetic raw materials for biodegradable materials. By copolymerizing with other biodegradable monomers, composite materials with excellent biodegradability and mechanical properties can be prepared.
These composite materials have broad application prospects in packaging materials, agricultural films, and other fields, which can help reduce plastic pollution and protect the environment. In addition, 2-bromomalondialdehyde can also be used to treat harmful substances in industrial wastewater. By introducing 2-bromomalondialdehyde, it can react with harmful substances in wastewater and convert them into harmless or low toxicity substances. This method not only helps to purify wastewater and protect the environment, but also enables the resource utilization of waste.
2-Bromomalonaldehyde (CAS number 2065-75-0) is an organic compound with the molecular formula C ∝ H ∝ BrO ₂, with a molecular weight of 150.96 g/mol, typically present in the form of a light yellow solid. The molecular structure contains two electrophilic aldehyde carbons and a bromine atom that is easily replaced by nucleophiles. This unique structure makes it a powerful "synthetic molecule" and has shown wide application value in various fields such as medicine, materials science, and biochemistry research.
In the field of materials science: promoting the development of new functional materials
Synthesis of Liquid Crystal Materials
It is an important raw material for synthesizing certain special liquid crystal molecules. Liquid crystal materials are widely used in display technologies such as LCD and OLED, and their performance directly affects key indicators such as clarity, response speed, and energy consumption of display devices. With the continuous upgrading of display technology and the increasing demand for high-performance display materials, although the application in the synthesis of liquid crystal materials is not as extensive as in the pharmaceutical field, it is still a stable source of demand.
Development of organic optoelectronic materials
The synthesized heterocyclic compounds have become ideal candidate molecules for the development of materials such as organic light-emitting diodes (OLEDs), organic solar cells (OPVs), and organic field-effect transistors (OFETs) due to their excellent conjugation system and photoelectrochemical activity. Specific applications include:
OLED materials: Heterocyclic compounds derived from 2-bromomalondialdehyde can be used as luminescent layer materials to achieve different colors of luminescence by adjusting their molecular structure, thereby improving the luminescence efficiency and stability of OLEDs.
OPV material: As a donor or acceptor material, its derived heterocyclic compounds can optimize the light absorption range and charge transfer performance, and improve the photoelectric conversion efficiency of OPV.
OFET materials: By utilizing the semiconductor properties of heterocyclic compounds derived from 2-bromomalondialdehyde, high-performance OFETs can be prepared for use in fields such as flexible electronics and smart sensors.
With the rapid development of the organic electronics industry, the demand for basic building blocks is expected to see new growth.
Field of Biochemistry Research: Revealing the Chemical Mechanisms of Life Processes
Research on DNA damage and repair mechanisms
It can be used as a chemical probe to form adducts by reacting with nucleic acid bases such as guanine, helping scientists explore the genetic toxicity of specific chemicals. For example, when studying the genetic toxicity of certain environmental pollutants or drug metabolites, 2-bromomalondialdehyde can simulate the reaction process between these substances and DNA, revealing their carcinogenic or mutagenic mechanisms.
2. Research on Enzyme Activity and Inhibition Mechanism
Its aldehyde group can covalently bind with the active center residue of the enzyme (such as the ε - amino group of lysine) to form stable adducts, thereby inhibiting the activity of the enzyme. This characteristic makes 2-bromomalondialdehyde an effective tool for studying the relationship between enzyme structure and function. For example, by reacting 2-bromomalondialdehyde with specific enzymes, the active site of the enzyme can be determined, further revealing the catalytic mechanism of the enzyme.
Other fields: Expanding application boundaries
Its high reactivity and multifunctionality make it an ideal model molecule for chemical synthesis methodology research. By studying the reaction of 2-bromomalondialdehyde with different reagents, new types of organic reactions can be developed, reaction conditions can be optimized, and reaction yields and selectivity can be improved. For example, by utilizing the reactivity of aldehyde groups and bromine atoms in 2-bromomalondialdehyde, multi-step cascade reactions can be designed to achieve efficient synthesis of complex molecules.
Catalyst design and screening
As a template molecule for catalyst design, new catalysts can be developed by simulating their reaction processes. For example, chiral catalysts can be designed to achieve asymmetric catalytic synthesis through the condensation reaction of 2-bromomalondialdehyde with nucleophilic reagents. In addition, 2-bromomalondialdehyde can also be used to screen catalyst libraries and search for catalysts with high activity and selectivity for specific reactions.
FAQ
Is 2-bromomalonaldehyde harmful?
Malondialdehyde (MDA) is the principal and most studied product of polyunsaturated fatty acid peroxidation. This aldehyde is a highly toxic molecule and should be considered as more than just a marker of lipid peroxidation.
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