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9,10-DIBROMOANTHRACENE is an organic compound with the chemical formula C14H8Br2. It is a white to light yellow solid with an odor similar to kerosene. This compound is insoluble in water (only soluble in hot water) and can be soluble in hot benzene and toluene, slightly soluble in many organic solvents such as alcohol, ether, and cold benzene, and insoluble in water. This compound has a UV absorption peak of 245nm, and due to its small intermolecular distance, it exhibits an ordered graphene structure at low temperatures. It is an aromatic compound with many useful chemical and physical properties. Mainly used as an intermediate in organic synthesis. It can also be used for the preparation of dyes, as well as applications in fluorescent probes, photoreceptors, and laser materials.
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Chemical Formula |
C14H8Br2 |
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Exact Mass |
334 |
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Molecular Weight |
336 |
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m/z |
336 (100.0%), 334 (51.4%), 338 (48.6%), 337 (9.7%), 339 (7.4%), 337 (5.4%), 335 (4.4%), 335 (3.3%) |
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Elemental Analysis |
C, 50.04; H, 2.40; Br, 47.56 |
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9,10-Dibromoanthracene is an organic compound with a unique chemical structure, with the molecular formula C ₁₄ H ₈ Br ₂ and a molecular weight of 336.02. This substance is a yellow powder at room temperature, which can sublime. It is slightly soluble in ethanol, ether, and benzene, soluble in chloroform and hot toluene, and insoluble in water. Its symmetrical molecular structure endows it with good stability and special electronic properties, making it widely applicable in multiple fields.
It is an important raw material for synthesizing luminescent materials such as organic light-emitting diodes (OLEDs). Its unique conjugated system enables it to absorb and emit light of specific wavelengths, thus playing a crucial role in light-emitting devices.
OLED materials: OLED materials with specific luminescent properties can be synthesized through selective bromine retention and coupling reactions. For example, through Suzuki coupling reaction, the substance can be reacted with arylboronic acid to generate arylanthracene compounds with specific luminescent wavelengths. These compounds have broad application prospects in fields such as OLED displays and lighting.
Fluorescent probe: Its derivatives can also be used as fluorescent probes for detecting heavy metal ions, organic pollutants, etc. in the environment. Its fluorescence performance can be regulated through molecular structure modification, thereby achieving specific recognition of different target substances.
Fine chemical manufacturing
In the field of fine chemical manufacturing, it also plays an important role. It can be used as one of the raw materials for synthesizing fine chemicals such as spices and dyes. Through precise chemical synthesis and processing, chemicals with specific aroma, color and other properties can be prepared.
Spice synthesis: Its derivatives have unique aromas and can be used to synthesize high-end spices. For example, 9,10-dibromoanthrene can be converted into 9,10-dihydroanthracene through reduction reaction, which has elegant flower fragrance and can be used to prepare perfume, cosmetics, etc.
Dye synthesis: It is a key intermediate for the synthesis of anthraquinone dyes. Anthraquinone dyes have the advantages of bright color and high wash fastness, and are widely used in industries such as textiles, leather, and papermaking. By changing the substituents or reaction conditions of 9,10-dibromoanthracen, anthraquinone dyes of different colors can be synthesized to meet the needs of different fields.
In the field of pesticides, it also has important applications. Its derivatives can be used as key intermediates for the synthesis of herbicides such as glyphosate in rice fields. Guacaotan is a selective non steroidal thiocarbamate herbicide used to control weeds in rice fields. Its mechanism of action is to achieve weed control by inhibiting the growth point cell division of weeds. Its derivatives play a crucial role in the synthesis of Guacaotan, converting it into compounds with herbicidal activity through specific chemical reactions.
Functional materials field
9,10-Dibromoanthracene can also be used to synthesize functional materials such as optoelectronic materials, magnetic materials, etc. Its unique chemical structure enables it to form specific interactions with other compounds, thereby endowing the material with special functions.
Optoelectronic materials: their derivatives can be used to synthesize photoelectric conversion materials, optical guiding materials, etc. These materials have broad application prospects in fields such as solar cells and optoelectronic devices.
For example, by combining it with conjugated polymers, materials with efficient photoelectric conversion properties can be synthesized to improve the conversion efficiency of solar cells.
Magnetic materials: their derivatives can also be used for synthesizing magnetic materials. By introducing magnetic groups or combining with other magnetic compounds, materials with specific magnetic properties can be prepared. These materials have potential applications in fields such as data storage and magnetic sensors.
Research reagent field
In the field of scientific research, as an important organic reagent, it is widely used in organic synthesis methodology research, reaction mechanism exploration, and other aspects. Its stable chemical properties and high reactivity make it an ideal model compound for studying organic chemical reactions. Researchers can reveal the laws and mechanisms of organic chemical reactions by studying their reaction characteristics, providing theoretical support for the development of new drugs and the synthesis of new materials.
With the increasing awareness of environmental protection, its application in the field of environmental protection has gradually received attention. Its derivatives can be used as fluorescent probes or adsorbents for detecting and removing heavy metal ions, organic pollutants, etc. in the environment. For example, by combining 9,10-dibromoanthracene with functionalized materials, composite materials with high adsorption performance can be prepared for the treatment of heavy metal ions and organic pollutants in wastewater.
For the complex conversion process of synthesizing 9,10-DIBROMOANTHRACEN from cyclohexane, it is indeed quite extensive. Here, we will attempt to provide a general description of a possible synthesis pathway and provide chemical equations and brief explanations for the key steps.
A rough path for the synthesis of 9,10-dibromoanthrene
Purpose: To convert cyclohexane into more reactive open chain compounds, such as cyclohexanol, cyclohexanone, or corresponding carboxylic acids.
Chemical equation (taking cyclohexanol as an example, it may actually generate cyclohexanone or carboxylic acid):
C6H12 + O2 → C6H12O + H2O
(Note: This reaction requires a catalyst, such as cobalt or manganese oxide, and reaction conditions may include high temperature and pressure.)
However, the yield of directly oxidizing cyclohexane to cyclohexanol or cyclohexanone may not be high, and further processing of these intermediates is required in subsequent steps. In practical synthesis, other more effective methods may be chosen to introduce unsaturated bonds.
Purpose: To increase the unsaturation in molecules by eliminating or rearranging reactions, in preparation for subsequent cyclization reactions.
Example step: Assuming we choose to start from cyclohexanone (although it is not the most direct product obtained directly from cyclohexane oxidation, it is one of the commonly used starting materials in synthesis).
Chemical equation (taking the conversion of cyclohexanone to cyclohexene as an example, dehydration after Clemson reduction):
C6H10O+H2 → C6H12O (Clemson reduction to produce cyclohexanol)
C6H12O → C6H10 (dehydration to produce cyclohexene)
However, please note that Clemson reduction is typically used for the reduction of carbonyl to methylene groups, rather than directly generating alcohols before dehydration. This is just to illustrate possible directions. In fact, unsaturated hydrocarbons may be directly obtained from cyclohexanone through other pathways, such as the Weickheimer reaction.
Purpose: To convert unsaturated hydrocarbons into aromatic hydrocarbons through cyclization reactions.
Example step: Due to the difficulty in constructing complex aromatic systems (such as anthracene) directly from simple unsaturated hydrocarbons such as cyclohexene, it is usually necessary to introduce more functional groups and complex reaction steps. We will not provide a detailed description of the specific reaction pathway here, but we can envision a series of reactions, including Diels Alder reaction, aromatic electrophilic substitution, aromatic nucleophilic substitution, condensation reaction, etc., to gradually construct the skeleton of the target molecule.
Objective: To introduce bromine atoms at specific positions in the aromatic ring.
Chemical equation (using hypothetical aromatic hydrocarbon precursors as an example):
ArH + Br2 + FeBr3 → ArBr + HBr
Here, ArH represents the assumed precursor of aromatic hydrocarbons, and ArBr represents the product of brominated aromatic hydrocarbons. More complex catalysts and conditions may be required in actual reactions
However, due to the specificity of 9,10-dibromoanthrene (i.e. the bromine atom is located at the junction of two benzene rings), direct bromination may not be able to precisely control the position of the bromine atom. Therefore, it may be necessary to achieve this goal through strategies such as protecting groups, locating groups, or selective bromination reagents.
Objective: To obtain high-purity 9,10-dibromoanthrene through separation and purification steps.
Method: This usually includes techniques such as recrystallization, distillation, chromatographic separation (such as column chromatography, thin-layer chromatography, or high-pressure liquid chromatography), etc. The specific choice depends on the properties of the target product, the type and quantity of impurities, and the available equipment in the laboratory.
9,10-Dibromoanthracene is prepared by co-sublimation of anthracene with bromine and iron powder (or iron tribromide). Concrete synthetic route is as follows:
Raw materials:
Anthracene, bromine, iron powder or iron tribromide, ethylene glycol or toluene.
Step 1:
Dissolve anthracene in toluene 2.5 times the mass of anthracene.
01
Step 2:
Add an equal amount of boric acid to the melted anthracene, and stir rapidly at room temperature until it cools down.
02
Step 3:
Place the glass test tube containing ferric tribromide or iron powder in a sand bath, and dry it at 100°C for 1 h to sublimate it.
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Step 4:
The sublimation product was filtered and washed in 500 mL of dichloromethane.
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Step 5:
Recrystallize the washed product in a mixture of n-hexane and ethanol to obtain it.
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In summary, it is an important aromatic compound with a wide range of applications, including in the fields of organic synthesis, materials science, optoelectronics, etc. It can be prepared by sublimating anthracene with bromine and iron powder or iron tribromide, and the production process is relatively simple.
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