4-Chlorobenzyl mercaptan is an organic compound with the molecular formula C7H6ClS, CAS 6258-66-8. Low melting point crystals have a unique pungent odor, which is caused by the presence of thiol groups. It can dissolve in water to form a light yellow to yellow solution. However, it also has properties that are slightly soluble in ethanol and ether. Its high boiling point makes it difficult to evaporate at room temperature. However, under high temperature conditions, it can gradually evaporate. The viscosity is relatively low, with a viscosity index of about 16.7, indicating that the compound has a relatively small viscosity change during temperature changes, which is beneficial for its industrial application. It has extensive application value in many fields. Due to its unique chemical structure and properties, it plays an important role in the synthesis of intermediates, antibiotics, pesticides, dyes, chemical analysis, laboratory research, and other fields.
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Chemical Formula |
C7H7ClS |
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Exact Mass |
158 |
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Molecular Weight |
159 |
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m/z |
158 (100.0%), 160 (32.0%), 159 (7.6%), 160 (4.5%), 161 (2.4%), 162 (1.4%) |
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Elemental Analysis |
C, 53.00; H, 4.45; Cl, 22.35; S, 20.21 |
4-Chlorobenzyl mercaptan has a wide range of uses in the synthesis of intermediates. These applications cover multiple fields such as antibiotics, pesticides, dyes, pharmaceutical intermediates, polymer materials, surfactants, and spices. Understanding these uses will help to better utilize the potential value and application prospects of 4 chlorobenzyl mercaptan.
1. Synthesis of aminoglycoside antibiotics: 4-chlorobenzylthiol is an important intermediate in the synthesis of aminoglycoside antibiotics, such as streptomycin, gentamicin, etc. These antibiotics are mainly used to treat bacterial infections and have broad-spectrum antibacterial effects. By using 4-chlorobenzylthiol as an intermediate, these antibiotics can be more conveniently synthesized, improving production efficiency and reducing costs.
2. Synthesis of herbicides: 4-chlorobenzylthiol can also be used to synthesize herbicides. Herbicides are pesticides used to control weed growth and play an important role in agricultural production. Using 4 chlorobenzyl mercaptan as an intermediate can more efficiently synthesize herbicides and endow them with new properties and characteristics.
3. Synthesis of insecticides: 4-chlorobenzylthiol can also be used to synthesize insecticides. Insecticides are mainly used for controlling diseases and pests, and play an important role in protecting crops and forests. By using 4 chlorobenzyl mercaptan as an intermediate, new insecticides can be synthesized to improve their control effectiveness against specific pests.
4. Synthesis of Azo Dyes: 4-Chlorobenzylthiol is commonly used in the dye industry to synthesize azo dyes. Azo dyes are an important type of dye, widely used in fields such as textile printing and dyeing, coatings, etc. By using 4-chlorobenzylthiol as an intermediate, azo dyes can be more conveniently synthesized and given new colors and properties.
5. Synthesis of pharmaceutical intermediates: 4-chlorobenzylthiol can also be used to synthesize various pharmaceutical intermediates. These intermediates can be used for further synthesis of drugs, alkaloids, and other compounds. By using 4-chlorobenzylthiol as an intermediate, these pharmaceutical intermediates can be synthesized more efficiently, providing support for drug research and production.
6. Synthesis of polymer materials: 4 chlorobenzyl mercaptan can also be used to synthesize polymer materials. Polymer materials are an important class of materials widely used in fields such as chemical engineering, light industry, and textiles. By using 4 chlorobenzyl mercaptan as an intermediate, new polymer materials can be synthesized and endowed with new properties and characteristics.
7. Synthesis of surfactants: 4-chlorobenzylthiol can also be used to synthesize surfactants. Surfactants are a class of compounds with surface activity, widely used in fields such as washing and cosmetics. By using 4 chlorobenzyl mercaptan as an intermediate, it is more convenient to synthesize surfactants, improve the surface activity and application effect of the product.
8. Synthesis of spices: 4-chlorobenzyl mercaptan can also be used to synthesize spices. Spices are a type of compound that can produce fragrance and are widely used in fields such as daily chemicals and food. By using 4 chlorobenzyl mercaptan as an intermediate, new spices can be synthesized and given new fragrances and properties.
Chemical equation:
Reaction of phenol with sulfur chloride:
C6H5OH + 2NaOH + 2S2Cl2 → C6H5SCH2CH2CH2SCH2CH2C6H5 + 3NaCl + 3H2O
In this reaction, phenol undergoes a substitution reaction with sulfur chloride under the action of sodium hydroxide, resulting in the intermediate of dichlorophenol pentasulfide and sodium chloride. The intermediate of dichlorophenol pentasulfide is further converted into 4 chlorobenzyl mercaptan through subsequent reaction steps.
Synthesis reaction of chlorobenzyl mercaptan:
C6H5SCH2CH2CH2SCH2CH2C6H5 + 3NaOH → C6H4(Cl)CH2SH + 3NaCl + 3H2O
In this reaction, the intermediate of dichlorophenol pentasulfide undergoes a hydrolysis reaction under the action of sodium hydroxide, removing two sulfur atoms to generate 4 chlorobenzyl mercaptan. Simultaneously generate sodium chloride and water.
The method for synthesizing 4-chlorobenzyl mercaptan in the laboratory can use the following steps:
1. Prepare reagents and equipment: Prepare the necessary raw materials and reagents, including phenol, sulfur chloride, sodium hydroxide, chloroform, magnetic stirrer, thermometer, drip funnel, round bottom flask, etc.
2. Dissolve phenol: Dissolve phenol in chloroform to form a chloroform solution of phenol.
3. Add sodium hydroxide: Add sodium hydroxide to a chloroform solution of phenol and stir evenly.
4. Dropwise addition of sulfur chloride: Slowly add sulfur chloride to a chloroform solution of phenol, and control the reaction temperature between 50-60 ℃.
5. Reaction stirring: After adding sulfur chloride dropwise, continue stirring for about 2 hours to allow the reaction to proceed fully.
6. Filter separation: Filter the reaction solution, remove insoluble substances, and collect the filtrate.
7. Water washing: Wash the filter residue with an appropriate amount of water to remove unreacted phenol.
8. Drying: Combine the filtrate and washing solution, and dry with anhydrous sodium sulfate.
9. Distillation: Distill the dried filtrate to remove chloroform and other volatile components.
10. Refining: Dissolve the distilled product in ethanol, add a sodium hydroxide solution, heat and reflux for about 1 hour to further purify the product.
11. Cooling filtration: After cooling, filter to remove insoluble substances.
12. Drying: Wash the filter residue with an appropriate amount of water to remove unreacted phenol.
13. Purification: Combine the filtrate and washing solution, dry with anhydrous sodium sulfate, and obtain the crude 4 chlorobenzyl mercaptan.
14. Crystallization and separation: The crude product is crystallized and separated to obtain high-purity 4 chlorobenzyl mercaptan crystals.
In the late 19th and early 20th centuries, chemists began to attempt the synthesis of 4-chlorophenylmercaptan. The initial method was mainly based on the reaction of chlorohydrazine chloride with sulfur-containing compounds. Chlorobenzoyl chloride, as a common chlorinated aromatic hydrocarbon, has a certain reactivity with the chlorine atom on its benzene ring, which can undergo substitution reactions with nucleophiles.
Scientists attempted to use inorganic sulfides such as sodium sulfide and sodium sulfide to react with 2-chlorophenylhydrazine chloride, hoping to obtain 4-chlorophenylhydrazine mercaptan. However, due to the difficulty in controlling reaction conditions, various by-products are often produced in the product, resulting in low yield and purity. In order to improve the synthesis yield and purity of 4-chlorobenzenes, chemists conducted in-depth research and optimized the reaction conditions.
They found that factors such as reaction temperature, reaction time, solvent selection, and raw material ratio have a significant impact on the reaction results. For example, at lower temperatures, the reaction rate is slower, but the number of side reactions is less; At high temperatures, the reaction rate accelerates, but the number of side reactions also increases accordingly.
Through extensive experimental exploration, scientists gradually found the optimal reaction conditions. For example, by reacting 2-chlorobenzoyl chloride with sodium thiosulfate in an appropriate solvent and then treating with acid, the yield and purity of 4-chlorophenylmercaptan can be effectively improved.
Accurately identifying the structure of 4-chlorophenylmercaptan becomes crucial after its successful synthesis. At the beginning of the 20th century, with the development of spectroscopic analysis techniques such as infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), and mass spectrometry (MS), chemists were able to more accurately determine the structure of organic compounds.
Through infrared spectroscopy analysis, the functional groups present in the compound, such as the stretching vibration peaks of thiol groups, can be determined to have characteristic absorption in the infrared spectrum.
Nuclear magnetic resonance spectroscopy can provide chemical environmental information of hydrogen and carbon atoms in molecules, thereby inferring the structure of molecules. Mass spectrometry analysis can determine the relative molecular mass and fragment ion information of molecules, further verifying their structure. After determining the structure of 4-chlorophenylthiol, chemists conducted in-depth research on its physical and chemical properties. Research has found that 4-chlorophenylmercaptan is a low melting point crystal with a pungent odor. Its melting point is 19-20 ° C, relative density is 1.202 g/mL (at 25 ° C), boiling point is 125 ° C (35mmHg), and flash point is 76 ° C. These physical properties provide important references for the storage, transportation, and use of 4-chlorophenyl mercaptan.
In addition, chemists have studied the solubility, stability, and other properties of 4-chlorobenzenes and found that they have good solubility in certain organic solvents, but are prone to decomposition under light and high temperature conditions.
adverse reaction
4-Chlorobenzyl Mercaptan (CAS number 6258-66-8) is a sulfur-containing organic compound with the molecular formula C ₇ H ₇ ClS. It appears as a white to pale yellow liquid or solid at room temperature and has a strong pungent odor. The chlorine atoms and thiol groups (- SH) contained in its chemical structure endow it with unique reactivity, but at the same time, it may also trigger a series of adverse reactions.
Toxicity mechanism and contact route
Toxicity mechanism
The toxicity of 4-Chlorobenzyl Mercaptan mainly stems from two key parts of its chemical structure:
Chlorine atom (Cl): Chlorinated aromatic hydrocarbons may generate active intermediates (such as chloroquinones) through metabolism, triggering oxidative stress reactions and damaging cell membranes, proteins, and DNA.
Thiol group (- SH): Thiol groups have high reactivity and can bind to metal ions (such as copper and iron), interfering with enzyme activity; At the same time, it is possible to disrupt cellular function by covalently modifying cysteine residues in proteins.
Contact route
Inhalation: Its volatility may lead to the presence of vapor in the air, especially in high temperature or poorly ventilated environments where the concentration increases. Inhalation can directly irritate the respiratory mucosa.
Skin contact: Liquid or solid particles can be absorbed through the skin, especially on damaged skin, causing local or systemic toxicity.
Eye contact: Direct splashing into the eyes may cause serious irritation and even corneal damage.
Accidental ingestion: Although not a common route, accidental ingestion may cause gastrointestinal reactions and systemic toxicity.
Toxicity mechanism and contact route
Toxicity mechanism
The toxicity of 4-Chlorobenzyl Mercaptan mainly stems from two key parts of its chemical structure:
Chlorine atom (Cl): Chlorinated aromatic hydrocarbons may generate active intermediates (such as chloroquinones) through metabolism, triggering oxidative stress reactions and damaging cell membranes, proteins, and DNA.
Thiol group (- SH): Thiol groups have high reactivity and can bind to metal ions (such as copper and iron), interfering with enzyme activity; At the same time, it is possible to disrupt cellular function by covalently modifying cysteine residues in proteins.
Contact route
Inhalation: Its volatility may lead to the presence of vapor in the air, especially in high temperature or poorly ventilated environments where the concentration increases. Inhalation can directly irritate the respiratory mucosa.
Skin contact: Liquid or solid particles can be absorbed through the skin, especially on damaged skin, causing local or systemic toxicity.
Eye contact: Direct splashing into the eyes may cause serious irritation and even corneal damage.
Accidental ingestion: Although not a common route, accidental ingestion may cause gastrointestinal reactions and systemic toxicity.
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