1,4-Bis(bromomethyl)benzene CAS 623-24-5

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1,4-Bis(bromomethyl)benzene, also known as p-xylylenebis(bromomethyl) or 1,4-dibromomethylbenzene, is a chemical compound with the molecular formula C8H8Br2. This aromatic hydrocarbon derivative features a benzene ring substituted at the 1 and 4 positions with bromomethyl (CH2Br) groups.

In addition, its structure, characterized by two bromine atoms separated by a flexible four-carbon chain, offers unique opportunities in the design of cross-linking agents and materials with enhanced thermal or mechanical properties. Researchers often exploit its reactive bromine moieties for the synthesis of flame-retardant materials and other advanced applications where controlled molecular architectures are crucial.

Overall, it stands out as a versatile building block in organic synthesis, contributing to the development of innovative chemical products across multiple industries.

Its two bromomethyl groups can be readily transformed into other functional groups, making it a versatile building block for the synthesis of complex organic molecules.

In protection reactions, it is particularly useful for protecting hydroxyl (OH) or amino (NH2) groups. These groups are often reactive and need to be protected during certain steps of a synthesis to prevent unwanted side reactions. By reacting the hydroxyl or amino group with one of the bromomethyl groups, a stable, easily removable protecting group is introduced. This protecting group can later be removed under specific conditions to restore the original hydroxyl or amino group.

The use in protection reactions is advantageous because it allows for the selective protection of hydroxyl or amino groups in the presence of other functional groups. This selectivity is crucial in complex organic syntheses, where precise control over the reaction sequence and product structure is required.

Overall, it is a valuable intermediate in organic synthesis and pharmaceutical chemistry, with a wide range of applications in the synthesis of complex organic molecules and the protection of reactive functional groups.

The high chemical reactivity of 1,4-bis(bromomethyl)benzene allows it to undergo nucleophilic substitution reactions with a variety of nucleophiles, including alcohols, amines, and thiols.

In these reactions, the bromine atom in the bromomethyl group is replaced by a nucleophile, leading to the formation of corresponding debrominated functional group products. For example, when reacted with an alcohol, an ether linkage is formed; when reacted with an amine, an alkylamine linkage is formed; and when reacted with a thiol, a thioether linkage is formed.

The nucleophilic substitution reactions are typically carried out in polar solvents, such as dimethylformamide (DMF) or dimethyl sulfoxide (DMSO), at temperatures ranging from room temperature to reflux. The choice of solvent and temperature can affect the reaction rate and selectivity.

The versatility in undergoing nucleophilic substitution reactions makes it a valuable intermediate in the synthesis of a wide range of organic compounds. By selecting the appropriate nucleophile and reaction conditions, researchers can synthesize compounds with specific functional groups and chemical properties tailored to their needs.

Selective conversion of one of the benzyl bromide groups can be achieved by using a limiting amount of the nucleophile or by employing conditions that favor monosubstitution. For example, by using a substoichiometric amount of the nucleophile or by conducting the reaction at lower temperatures, it is possible to obtain a mixture in which the monosubstituted product predominates.

Conversely, to achieve conversion of both benzyl bromide groups, an excess of the nucleophile and more forcing conditions (such as higher temperatures or the use of a catalyst) may be required. By carefully controlling these reaction parameters, researchers can obtain the desired monosubstituted or disubstituted product with high selectivity.

The ability to selectively convert one or both benzyl bromide groups in 1,4-bis(bromomethyl)benzene is significant for precise control in organic synthesis. It allows researchers to synthesize compounds with specific functional group patterns and chemical properties, enabling the preparation of target products with high purity and yield. This level of control is crucial in the development of new pharmaceutical agents, materials, and other organic compounds with specific applications.

In the synthesis of optoelectronic materials

 

It can be used as a precursor for the preparation of conjugated polymers and oligomers. By reacting with various aromatic compounds containing nucleophilic substituents, such as amines or thiols, researchers can synthesize polymers and oligomers with extended conjugation and tailored electronic properties. These materials can be used in a variety of optoelectronic applications, such as organic light-emitting diodes (OLEDs), solar cells, and field-effect transistors.

In the synthesis of fluorescent probes

 

It can be used to introduce bromine atoms into the structure of the probe, which can serve as reactive sites for further modification or as quenchers of fluorescence. By carefully controlling the reaction conditions and reactant ratios, researchers can synthesize probes with specific spectral properties and binding affinities tailored to their target analytes. These probes can be used in various biological and analytical applications, such as imaging, sensing, and diagnostics.

In the synthesis of coordination compounds

 

It can be used as a ligand or precursor for the preparation of metal-organic frameworks (MOFs) and other coordination polymers. By reacting with metal ions or metal complexes, researchers can synthesize materials with unique structures and properties that can be used in a variety of applications, such as gas separation, catalysis, and drug delivery.

Fluorescent probes are versatile tools widely employed in various scientific and industrial fields, including biochemistry, medicine, environmental monitoring, and materials science. These probes operate on the principle of fluorescence, a phenomenon where a molecule absorbs light of a specific wavelength (excitation) and then emits light of a longer wavelength (emission). This process allows for the detection and quantification of analytes with high sensitivity and specificity.

The core of a fluorescent probe typically consists of a fluorophore, which is responsible for the fluorescence, and a recognition moiety that selectively binds to the target analyte. When the recognition moiety interacts with its target, it can induce changes in the fluorophore's properties, such as an alteration in fluorescence intensity, wavelength, or lifetime. These changes serve as the basis for signaling the presence and often the concentration of the analyte.

Fluorescent probes are highly valued for their non-invasive nature, real-time monitoring capabilities, and the ability to provide spatial and temporal information about biological processes or environmental contaminants. For instance, in biomedical research, they are used to track cellular activities like ion concentrations, protein-protein interactions, and enzyme activities. In environmental science, they help detect pollutants like heavy metals, pesticides, and explosives in water, soil, and air samples.

Advancements in synthetic chemistry have led to the development of probes with enhanced properties, such as improved selectivity, sensitivity, and stability. Furthermore, the integration of fluorescent probes with advanced imaging techniques, like confocal microscopy and super-resolution imaging, has expanded their application horizon, enabling researchers to visualize and understand complex biological structures and functions at unprecedented resolutions.

In summary, fluorescent probes represent a powerful class of analytical tools that enable precise, sensitive, and real-time detection of analytes across diverse disciplines. Their continued evolution promises to unlock new insights and drive innovations in science and technology.

1,4-Bis(bromomethyl)benzene, also known as p-xylylenebis(bromomethyl), is a chemical compound renowned for its flame retardant properties. This aromatic hydrocarbon derivative features a benzene ring substituted at the 1 and 4 positions with bromomethyl groups, which impart its flame-retarding capabilities.

The brominated structure of 1,4-bis(bromomethyl)benzene plays a crucial role in its flame retardancy. When this compound is incorporated into polymers or other materials, the bromine atoms act as effective flame inhibitors. During combustion, the bromine atoms release bromine radicals, which interfere with the chain reaction of the flame, thereby slowing down or extinguishing the fire.

Moreover, the aromatic nature of the benzene ring enhances the thermal stability of the compound, allowing it to withstand higher temperatures without decomposing. This stability further contributes to its effectiveness as a flame retardant.

The application of hard templates and precursors in the preparation of carbon nanomaterials

1,4-Bis(bromomethyl)benzene is an important organic intermediate. Its molecular structure contains two bromomethyl substituents, located at the para positions of the benzene ring. This unique structure gives it dual functions in the preparation of carbon nanomaterials: as a hard template, its rigid benzene ring framework can construct ordered pore structures; as a precursor, the reactivity of the bromomethyl groups enables it to be transformed into a carbon skeleton through thermal decomposition or catalysis, while releasing hydrogen bromide to regulate the reaction process.

I. As a hard template: Construction of ordered carbon nanostructures

The benzene ring structure of 1,4-dibromomethylbenzene is highly rigid. It can self-assemble into an ordered arrangement under high temperature or solvent evaporation conditions. For example, in the process of nano casting or solvent evaporation-induced self-assembly (EISA), its molecules form a periodic structure through π-π stacking and van der Waals forces, and then the template structure is transformed into a carbon material through carbonization or chemical vapor deposition (CVD) technology. Studies have shown that the mesoporous carbon materials prepared using 1,4-dibromomethylbenzene as a template have a high specific surface area (>1000 m²/g) and a uniform pore size distribution (2-10 nm), which are suitable for use as electrode materials for supercapacitors.

Furthermore, the steric hindrance effect of the bromomethyl group can regulate the pore shape of the template. For instance, by adjusting the reaction conditions (such as solvent polarity and temperature), the plane of the benzene ring can form a specific angle with the bromomethyl chain, thereby inducing the generation of hexagonal, cubic or layered mesoporous structures. This structural controllability provides an important means for designing functionalized carbon nanomaterials.

 

II. As a precursor: Pyrolysis to generate carbon framework and regulation of reaction by bromide hydride

The pyrolysis process of 1,4-dibromomethylbenzene involves the cleavage of bromomethyl groups and the carbonization of the benzene ring. When heated to 400-800°C in an inert atmosphere (such as nitrogen), the bromomethyl group (-CH₂Br) first loses bromide hydride (HBr) to form the intermediate 1,4-dimethylbenzene (para-xylene), and then further undergoes dehydrogenation and carbonization to form graphitized carbon structure. The released HBr in this process can act as a catalyst, promoting the rearrangement of the carbon framework and defect repair, thereby enhancing the conductivity of the material.

Furthermore, 1,4-dibromomethylbenzene can also be mixed with other carbon sources (such as phenolic resins, sucrose), and the cross-linking effect of the bromomethyl groups can enhance the thermal stability of the precursor. For example, when preparing carbon/carbon composite materials, the bromomethyl groups react with the phenolic hydroxyl groups to form a three-dimensional cross-linked network, effectively inhibiting the volume shrinkage during the thermal decomposition process and improving the mechanical strength of the material.

 

III. Application Examples: Synthesis of Carbon Nanotubes and Graphene

In the preparation of carbon nanotubes, 1,4-dibromomethylbenzene can serve as both the carbon source and the precursor for the catalyst. The bromomethyl groups in this compound decompose at high temperatures to generate HBr, which can reduce the oxides of metal catalysts (such as iron, cobalt), promoting the nucleation and growth of carbon nanotubes. At the same time, the planar structure of the benzene ring provides a growth template for carbon nanotubes, facilitating the formation of highly oriented tube bundles.

In the preparation of graphene, 1,4-dibromomethylbenzene can be obtained through the chemical exfoliation method. The strong electron-withdrawing effect of the bromomethyl groups can weaken the van der Waals forces between graphite layers, promoting the intercalation and exfoliation of graphite. For example, when graphite is mixed with 1,4-dibromomethylbenzene and heated, the bromomethyl groups insert into the interlayer of graphite, and then single-layer or few-layer graphene can be obtained through ultrasonic treatment. This method has the advantages of simple operation and low cost, and is suitable for large-scale production.

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