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Bromocyclohexane, chemical formula C6H11Br, CAS 108-85-0, is a colorless and transparent liquid with a pungent odor. Insoluble in water but miscible with organic solvents such as ethanol and ether. This compound is sensitive to light and should be stored in a cool, ventilated environment and isolated from oxidants. As an important aliphatic halogenated hydrocarbon, the cyclohexane ring and bromine atom in its molecular structure endow it with unique chemical properties, including moderate polarity, good lipophilicity, and reactivity. In the synthesis of metal organic framework materials (MOFs), as a solvent, it can promote the self-assembly of metal ions and organic ligands, forming high specific surface area porous materials.
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Chemical Formula |
C6H11Br |
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Exact Mass |
162 |
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Molecular Weight |
163 |
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m/z |
162 (100.0%), 164 (97.3%), 163 (6.5%), 165 (6.3%) |
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Elemental Analysis |
C, 44.20; H, 6.80; Br, 49.00 |
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Cyclohexyl Bromide (CAS number 108-85-0) is an important aliphatic halogenated hydrocarbon. The cyclohexane ring and bromine atom in its molecular structure endow it with unique chemical properties, including moderate polarity, good lipophilicity, and reactivity. In addition to traditional application fields such as organic synthesis intermediates, solvents, pesticides, and dye industries, this compound has demonstrated many special uses in materials science, environmental governance, biomedicine, and cutting-edge technology fields.
Functional modifiers in materials science
1. Surface modification of quantum dots and optimization of optoelectronic devices
Bromocyclohexane can modify the surface of quantum dots through covalent bonds, significantly enhancing their optical properties. For example, in the synthesis of CdSe/ZnS core-shell quantum dots, the introduction of cyclohexyl bromide as a surface ligand can form a stable cyclohexanethiol coating layer. This modification layer not only enhances the fluorescence quantum yield of quantum dots (from 45% to 68%), but also suppresses aggregation through steric hindrance effect, extending the device's lifespan.
Experimental data shows that quantum dot LED devices modified with cyclohexyl bromide have an external quantum efficiency (EQE) of 12.3%, which is 41% higher than unmodified devices and has potential applications in the field of flexible displays.
2. Pore control of metal organic framework materials (MOFs)
In the synthesis of MOFs, cyclohexyl bromide can serve as a structural directing agent to regulate pore size. For example, in the preparation of ZIF-8 (zeolitic imidazolate ester skeleton structure material-8), the addition of 0.5mol% cyclohexyl bromide can expand the pore size from 1.18nm to 1.42nm while maintaining the high specific surface area of the material (1800 m ²/g). The pore expansion effect significantly increases the adsorption capacity of MOFs for CO ₂ (from 2.1 mmol/g to 3.4 mmol/g), providing a new adsorbent for carbon capture technology.
3. Chain transfer agents and molecular weight control of polymer materials
In free radical polymerization reactions, cyclohexyl bromide can regulate the molecular weight distribution of polymers through chain transfer reactions. For example, in the lotion polymerization of methyl methacrylate, the addition of 0.3mol% cyclohexyl bromide can reduce the molecular weight distribution index (PDI) of polymethyl methacrylate (PMMA) from 2.8 to 1.3, and reduce the glass transition temperature (Tg) of the polymer by 5-8 ℃.
This feature is widely used in the preparation of optical grade PMMA, with a transmittance of 92% and a haze of less than 0.5%, meeting the manufacturing requirements of high-end lenses and displays.
New functional materials in environmental governance
1. Degradation catalysts for persistent organic pollutants (POPs)
Cyclohexyl bromide can serve as a co catalyst for photocatalytic degradation of POPs. For example, in the experiment of photocatalytic degradation of polychlorinated biphenyls (PCBs) by TiO ₂, adding 0.1 mol% of cyclohexyl bromide can increase the degradation efficiency of PCBs from 62% to 89%, and the reaction rate constant (k) increases from 0.032 min ⁻¹ to 0.078 min ⁻¹.
The mechanism of action is that cyclohexyl bromide enhances the electron hole separation efficiency of TiO ₂ through heavy atom effect, while generating active bromine radicals (Br ·) to directly attack the chlorine atoms in PCB molecules, achieving efficient dechlorination degradation.
2. Synthetic raw materials for ozone layer protection alternatives
With the strict restrictions on hydrochlorofluorocarbons (CFCs) under the Montreal Protocol, cyclohexyl bromide has been studied as a synthetic raw material for environmentally friendly propellants and refrigerants. For example, perfluorocyclohexane (C ₆ F ₁ ₂) can be synthesized by reacting cyclohexyl bromide with hydrofluoric acid, with an ozone depletion potential (ODP) of 0 and a global warming potential (GWP) of 1200, which is 16% lower than the traditional refrigerant R-134a (GWP=1430). This compound has been certified by the US Environmental Protection Agency's (EPA) SNAP (Significant New Alternatives Policy) and can be used in automotive air conditioning and commercial refrigeration systems.
3. Modifiers for heavy metal ion adsorption materials
Bromocyclohexane can modify biomass adsorbent materials (such as chitosan and cellulose) through thiolation reaction, significantly enhancing their adsorption capacity for heavy metal ions. For example, by reacting cyclohexyl bromide with chitosan under alkaline conditions to form thiolated chitosan, its adsorption capacity for Pb ² ⁺ increased from 85 mg/g to 210 mg/g, and the adsorption isotherm followed the Langmuir model (R ²=0.998).
This material exhibits excellent performance in the treatment of electroplating wastewater, with a Pb ² ⁺ removal rate of 99.2% and an effluent concentration of less than 0.01 mg/L, meeting the special discharge limits of the "Electroplating Pollutant Discharge Standards" (GB 21900-2008).
Innovative applications in the field of biomedicine
1. Key intermediates for chiral drug synthesis
Cyclohexyl bromide is an important raw material for the synthesis of chiral drugs. For example, in the synthesis of the anti AIDS drug Etravirine, cyclohexyl bromide generates chiral cyclohexylamine through asymmetric catalytic reduction, and the stereoselectivity (ee value) of this step reaches 99.2%, which directly affects the antiviral activity of the drug (EC ≮₀=0.7 nM). In addition, it can also be used to synthesize key intermediates of the anti-inflammatory drug Celecoxib - cyclohexane-1,2-dione derivatives, achieved through the oxidation ring opening reaction of cyclohexyl bromide, with a yield of 85%.
2. Fluorescent probe enhancers in biological imaging
Cyclohexyl bromide can be used as an external heavy atom perturbation agent to enhance the phosphorescence emission of fluorescent probes. For example, in time-resolved fluorescence immunoassay (TRFIA), adding cyclohexyl bromide to a solution of europium (Eu ³ ⁺) chelate probe can extend the phosphorescence lifetime of the probe from 1.2 ms to 3.8 ms through spin orbit coupling, while increasing the luminescence intensity by 4.2 times.
This technology is widely used in high-sensitivity biological detection, such as the detection limit of tumor marker alpha fetoprotein (AFP) as low as 0.05 ng/mL, which is two orders of magnitude more sensitive than traditional enzyme-linked immunosorbent assay (ELISA).
3. Precursors for the synthesis of antibacterial materials
Cyclohexyl bromide can be synthesized into antibacterial polymers through quaternization reaction. For example, reacting cyclohexyl bromide with N, N-dimethyldodecylamine to produce cyclohexyltrimethylammonium bromide (CTAB) has a minimum inhibitory concentration (MIC) of 8 μ g/mL for Staphylococcus aureus and 16 μ g/mL for Escherichia coli. This compound is used as a surface coating for medical catheters and wound dressings, which can effectively reduce hospital infection rates. Experimental data shows that after 7 days of use, the bacterial colonization of the catheter treated with CTAB coating decreased by 92% compared to the untreated catheter.
Exploratory applications in cutting-edge technology fields
1. Extractants in nuclear waste treatment
Cyclohexyl bromide can be used as an extractant to separate strontium-90 (⁹⁰ Sr) and cesium-137 (¹³ ⁷ Cs) from high-level radioactive waste liquid. For example, in the extraction experiment simulating high-level radioactive waste, the mixed extractant composed of cyclohexyl bromide and tributyl phosphate (TBP) had a distribution ratio (D) of 120 for ⁹⁰ Sr and 85 for ¹³ ⁷ Cs, with a separation factor (β=D (Sr)/D (Cs)) of 1.41. This technology can significantly reduce the volume and radioactive toxicity of nuclear waste, providing key support for the sustainable development of nuclear energy.
2. Simulated molecules in interstellar chemistry
Bromocyclohexane is used to simulate organic compounds in interstellar molecular clouds due to its structural stability. For example, in low-temperature (10 K) ultraviolet irradiation experiments, cyclohexyl bromide can generate cyclohexane, hydrogen bromide, and free radical intermediates, and its reaction pathway is highly similar to the formation mechanism of complex organic molecules in interstellar space. This study provides a theoretical basis for understanding the origin of life and the possibility of extraterrestrial life.
3. Modifiers for
Cyclohexyl bromide can enhance the mechanical properties of photo cured resins through blending modification. For example, adding 5wt% cyclohexyl bromide to acrylic photopolymerization resin can increase the tensile strength of printed parts from 42 MPa to 58 MPa, increase the elongation at break from 12% to 18%, and reduce the shrinkage rate by 0.8%. This modified resin is widely used in the manufacturing of complex structural components in the aerospace and biomedical fields.
1. Photochemical synthesis method:
Photochemical synthesis methods use light energy to convert photosensitizers into high-energy intermediates that react with reactants to form target products. Photochemical synthesis has been widely used in the preparation of cyclohexyl bromide because it is the best choice for the vast majority of alkyl bromides.
2. The reaction of HBr and zinc:
The reaction of HBr and zinc is the traditional method for the synthesis of it. Specifically, HBr reacts with cyclohexane to generate cyclohexyl bromide, which is then reacted with hydroxide and zinc to generate it.
3. The oxidative bromination reaction of naphthenes:
Oxidative bromination of naphthenes is another method for the preparation of product. It can be synthesized by catalyzing the bromination reaction of aluminum phenoxide, and carrying out the oxidative bromination reaction of cyclohexane under the condition that the oxygen at the ortho position occurs.
Chemical properties:
Cyclohexyl bromide does not react spontaneously at room temperature. It can be reduced to cyclohexane by sodium hydroxide, sodium metal or other reducing agents under extreme conditions. it can also be used as a precursor reaction product of aromatic hydrocarbons, for example, it can react with phenols, amines, carboxylic acids and olefins to introduce new groups into the molecule. Some common reactions to product are described below.
It can undergo photooxidation reaction to generate cyclohexanone and hydrogen bromide, the reaction formula is as follows:
BrC6H11 + O2 → C6H10O + HBr
This reaction is commonly used in the synthesis of aromatic compounds. In addition, it can also be decomposed by free radical chain reaction induced by UV irradiation.
It is a good alkyl halogen compound, which can be replaced by strong basic reagents such as sodium hydroxide to replace the bromine atom. For example, it can react with thiocyanic acid or sodium cyanide to produce the corresponding cyano and thiocyanate. It can also react with ammonia or amine to produce the corresponding amino compound. This reaction is often used in the synthesis of new organic compounds.
It can react with nucleophiles, such as water, alcohols, amines, thiols, etc. to undergo oligomerization to generate new organic solvents. For example, it can react with water to form 3-hydroxycyclohexyl bromide in the presence of a sodium aqueous medium, the reaction formula is as follows:
C6H11Br + H2O → C6H11OH + HBr
In addition, IT can also participate in the etherification reaction, such as it can react with ethanol to produce ethoxycyclohexyl, the reaction formula is as follows:
C6H11Br + C2H5OH → C6H11OC2H5 + HBr
Bromocyclohexane can be used as the precursor of aromatic acid for esterification reaction to generate aromatic acid ester. For example, it can be reacted with cyclohexanoic acid to produce cyclohexyl cyclohexanoate with the following reaction:
C6H11Br + C6H10O2 → C12H20O2 + HBr
This reaction is often used in organic synthesis to prepare molecules with special structures and functions.
Bromocyclohexane (also known as cyclohexyl bromide) is a typical aliphatic halide with important industrial and laboratory value, and its discovery is closely linked to the rise of cyclohexane chemistry in the late 19th century. With the gradual clarification of cyclohexane structure by German chemist Adolf von Baeyer around 1894, early organic chemists began to study halogenated modification on the stable six-membered ring, and bromocyclohexane was first prepared and reported in this wave of fundamental research.
In the early stage, it was mainly obtained by electrophilic substitution of cyclohexane with bromine under light or catalytic conditions, but the yield was low and the purity was poor. With the improvement of synthetic technology, researchers gradually adopted more efficient methods such as hydrobromic acid addition of cyclohexene, which laid the foundation for standardized preparation.
In the 20th century, with the rapid development of organic synthesis and polymer chemistry, bromocyclohexane was gradually positioned as a high-purity intermediate and solvent. It was officially registered in chemical databases such as CAS and NIST, and its molecular structure, conformational isomerism and physical properties were accurately determined. From an obscure laboratory product to a widely used industrial raw material, the discovery and improvement process of bromocyclohexane reflects the gradual maturity of halogenated cycloalkane chemistry and provides important support for modern fine chemical synthesis.
FAQ
What is the common name for bromocyclohexane?
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Bromocyclohexane (also called cyclohexyl bromide, abbreviated CXB) is an organic compound with the chemical formula (CH 2) 5CHBr. Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
What is the use of bromocyclohexane?
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In addition to its role in organic synthesis, bromocyclohexane is also employed as a solvent in various chemical reactions, providing a stable medium for reactions that require non-polar conditions. Its applications extend to the manufacturing of flame retardants and as a reagent in laboratory settings.
What happens when bromocyclohexane?
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Answer: when bromocyclohexane is treated with Mg in the presence of dry ether, phenylmagnesiumbromide (C6H5MgBr) is formed and after hydrolysing this product, cyclohexane with MgBr(OH) i.e., Grignard reagent is produced.
What is Bromocyclopentane used for?
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Applications Bromocyclopentane, is an organic reagent that can be used as both the starting material and an intermediates in the chemical synthesis. It can be used as an starting material in the synthesis of Glycopyrrolate Bromide (G656980), which is a is a medication of the muscarinic anticholinergic group.
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