(2-Bromoethyl)benzene is an organic compound. Molecular formula C8H9Br, CAS 103-63-9. This compound is formed by a bromine atom and a hydrogen atom on an ethyl substituted benzene ring. It is a colorless or light yellow liquid with an irritating odor. Soluble in most organic solvents, but insoluble in water. Under standard conditions, its solubility in water is extremely low. It can be used to synthesize some surfactants, such as soap, detergents, etc. These surfactants are widely used in fields such as cleaning and cosmetics.
It can be used to synthesize some functional materials, such as optoelectronic materials, sensor materials, etc. These functional materials have extensive applications in fields such as new energy and electronic information. It has important application value in the field of chemistry, especially in the manufacturing of plasticizers and other organic synthesis, playing a key role. With the development of technology and the deepening of research, the application fields of phthalic anhydride will further expand. At the same time, we should also pay attention to the safety and environmental issues during production and use, take scientific and reasonable measures to reduce potential risks, and promote sustainable development.
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Method 1:
Oxidative coupling reaction is an important organic synthesis method commonly used to construct carbon carbon bonds. During the reaction, two organic molecules undergo electron transfer under the action of oxidants, forming new carbon carbon bonds. In this experiment, benzene and bromoacetate undergo oxidative coupling reaction under the catalysis of copper salt, producing (2-bromoethyl) benzene.
Chemical equation
Reaction of ethyl bromoacetate with anhydrous copper chloride:
C2H5OC2H5+CuCl → C2H5OC2H4Cu+HCl
Oxidative coupling reaction:
C6H6+C2H4CuCl → C6H5CH2CH2Cl+C2H5OH
Neutralization reaction:
C6H5CH2CH2Cl+NaOH → C6H5CH2CH2OH+NaCl
Distillation separation:
C6H5CH2CH2OH → C6H5CH2CH2Cl+H2O
Experimental operation
(1) Add an appropriate amount of ethanol and ethyl bromoacetate to the beaker, stir and dissolve.
(2) Slowly add anhydrous copper chloride to the solution and observe a color change, indicating the start of the reaction.
(3) Slowly heat the mixture to reflux state and maintain for a certain period of time (about 2 hours).
(4) Stop heating and cool to room temperature.
(5) Pour the reaction solution into a separating funnel and wash with an appropriate amount of water to remove excess ethyl bromoacetate and ethanol.
(6) Neutralize the underlying solution with an appropriate amount of sodium hydroxide solution, and then wash with plenty of water.
(7) Dry the upper organic phase to remove moisture.
(8) Distill the dried organic phase and collect the target product (2-bromoethyl) benzene.
Method 2:
Ullmann reaction is a commonly used organic synthesis method for synthesizing aromatic compounds. In the reaction, aromatic compounds undergo coupling reactions with halogenated hydrocarbons catalyzed by copper salts, generating new carbon carbon bonds. In this experiment, benzene and cuprous bromide undergo Ullmann reaction under the catalysis of copper salts, producing (2-bromoethyl) benzene.
Experimental operation
(1) Add an appropriate amount of ethanol to the beaker, add cuprous bromide, and stir to dissolve it.
(2) Slowly add copper chloride to the solution and observe a color change, indicating the start of the reaction.
(3) Slowly heat the mixture to reflux state and maintain for a certain period of time (about 2 hours).
(4) Stop heating and cool to room temperature.
(5) Pour the reaction solution into a separating funnel and wash with an appropriate amount of water to remove excess cuprous bromide and ethanol.
(6) Neutralize the underlying solution with an appropriate amount of sodium hydroxide solution, and then wash with plenty of water.
(7) Dry the upper organic phase to remove moisture.
(8) Distill the dried organic phase and collect the target product (2-bromoethyl) benzene.
Chemical equation
Reaction between cuprous bromide and copper chloride:
CuBr+CuCl → CuCl2+CuBr2
Ullmann reaction:
C6H6+CuBr2 → C6H5CH2CH2Br+CuH
Neutralization reaction:
C6H5CH2CH2Br+NaOH → C6H5CH2CH2OH+NaBr
Distillation separation:
C6H5CH2CH2OH → C6H5CH2CH2Br+H2O
Method 3:
The diazotization reaction is a commonly used method for synthesizing aromatic compounds. In the reaction, aromatic compounds react with nitrite under acidic conditions to form diazonium salts. Then, diazonium salts can react with various electrophilic reagents to generate new carbon carbon bonds. In this experiment, aniline is converted into diazonium salts under acidic conditions, and then reacts with cuprous bromide to form (2-bromoethyl) benzene.
Experimental operation
(1) Add an appropriate amount of ethanol and aniline to the beaker and stir evenly.
(2) Slowly add sulfuric acid to the solution while maintaining the temperature between 0-5 ℃. When the solution turns yellow, it indicates that the diazotization reaction has begun.
(3) Slowly add sodium nitrite solution to the reaction solution while maintaining the temperature between 0-5 ℃. When the yellow color disappears and a red precipitate is formed, it indicates that the diazotization reaction has been completed.
(4) Add cuprous bromide to the reaction solution and stir evenly.
(5) Pour the reaction solution into a separating funnel and wash with an appropriate amount of water to remove excess cuprous bromide and ethanol.
(6) Neutralize the underlying solution with an appropriate amount of sodium hydroxide solution, and then wash with plenty of water.
(7) Dry the upper organic phase to remove moisture.
(8) Distill the dried organic phase and collect the target product (2-bromoethyl) benzene.
Chemical equation
Diazotization reaction of aniline:
C6H5NH2+HNO3 → C6H5N2HSO3Na+H2SO4
Reaction of diazonium salts with cuprous bromide:
C6H5N2HSO3Na+CuBr2 → C6H5CH2CH2Br+CuSO4+NaBr+HBr
Neutralization reaction:
C6H5CH2CH2Br+NaOH → C6H5CH2CH2OH+NaBr
Distillation separation:
C6H5CH2CH2OH → C6H5CH2CH2Br+H2O
Method 4:
In organic chemistry, electrophilic substitution reactions are a common type of reaction, especially in the reactions of aromatic compounds. In this reaction, an electrophilic reagent (such as hydrogen bromide) attacks a carbon atom of the aromatic ring, causing a hydrogen atom on the ring to be replaced. In this experiment, phenylethanol reacts with hydrogen bromide to produce (2-bromoethyl) benzene, and the reaction equation is as follows:
C6H5CH2OH+HBr → C6H5CH2CH2Br+H2O
Experimental steps
1. Experimental operation:
(1) In a dry beaker, add an appropriate amount of phenylethanol and catalyst.
(2) Place the beaker on a magnetic stirrer and stir at an appropriate temperature to ensure thorough mixing of the reactants.
(3) Slowly introduce hydrogen bromide gas into the beaker, paying attention to controlling the injection rate to maintain a smooth reaction.
(4) When a change in color is observed in the reaction mixture, it indicates that the reaction has begun. Continue to introduce hydrogen bromide until the reaction is complete.
(5) During the reaction process, a thermometer can be used to monitor the temperature to ensure that it remains stable within the appropriate range.
(6) After the reaction is completed, cool the reaction mixture to room temperature.
2. Product separation and purification:
(1) Separate the reaction mixture through a separating funnel to remove excess hydrogen bromide and unreacted phenylethanol.
(2) Dry the obtained organic phase using commonly used desiccants such as anhydrous magnesium sulfate or calcium chloride.
(3) Distill the dried organic phase to further purify the product. During the distillation process, temperature and pressure should be controlled to ensure the quality and yield of the product (2-Bromoethyl) benzene.
3. Product detection: Qualitative and quantitative analysis of products is carried out through methods such as chromatography, mass spectrometry, or nuclear magnetic resonance spectroscopy to ensure that the purity and yield of the products meet the requirements.
4. Post treatment and waste liquid treatment: Clean the experimental area and properly dispose of the waste liquid to ensure laboratory safety and environmental protection.