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1,2-Ethanedithiol(Ethan-1,2-dithiol) is a volatile liquid with a strong and unpleasant odor. Its molecular structure can be regarded as two carbon atoms in the ethane molecule each connected to a mercapto group. The chemical formula is C₂H₄(SH)₂. This unique double mercapto structure makes it a crucial type of bidentate ligand and an efficient reducing agent, especially widely used in organic synthesis and materials science. It can form stable chelates with heavy metal ions, thus playing a role in heavy metal detoxification and wastewater treatment.
At the same time, in peptide chemistry and polymer synthesis, it is specifically used for selective reduction of disulfide bonds or protection of carbonyl functional groups. Moreover, ethan-1,2-dithiol is a key precursor for preparing certain functional thiol-based polymer monomers and metal chalcogenide semiconductor nanocrystals. Due to its unpleasant odor and potential toxicity, all operations must be carried out carefully in a well-ventilated environment.
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Chemical Formula |
C2H6S2 |
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Exact Mass |
94 |
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Molecular Weight |
94 |
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m/z |
94 (100.0%), 96 (4.5%), 96 (4.5%), 95 (2.2%), 95 (1.6%) |
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Elemental Analysis |
C, 25.50; H, 6.42; S, 68.08 |
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Metal complexation field
1,2-ethanedithiol can form stable complexes with various transition metal ions such as copper, nickel, cobalt, etc. These complexes exhibit good activity and selectivity in catalyzing organic reactions. For example, in organic synthesis such as oxidation, reduction, and coupling reactions, ethan-1,2-dithiol-transition metal complexes can serve as catalysts to promote the reaction and improve the yield and purity of the product.
Specifically, the complex formed between ethan-1,2-dithiol and copper ions exhibits high efficiency in catalyzing the oxidation reaction of olefins. This complex can selectively oxidize specific positions of olefins to generate corresponding aldehydes, ketones, or carboxylic acids. In addition, ethan-1,2-dithiol-nickel complexes have a wide range of applications in catalytic hydrogenation reactions, which can efficiently reduce unsaturated compounds to saturated compounds.
In addition to transition metals, ethan-1,2-dithiol can also form complexes with rare earth metal ions for catalyzing certain specific organic reactions. Rare earth metals have unique electronic structures and catalytic properties, and the complexes formed with ethan-1,2-dithiol exhibit good effects in catalytic polymerization reactions, cyclization reactions, and other aspects.
For example, in catalyzing polymerization reactions of certain monomers, ethan-1,2-dithiol-rare earth metal complexes can serve as efficient catalysts to promote monomer polymerization and generate high molecular weight polymers. These polymers have broad application prospects in materials science, biomedical and other fields.
Ethan-1,2-dithiol as a metal chelating agent, can be used for the separation and enrichment of metal ions. By forming stable complexes with specific metal ions, ethan-1,2-dithiol can separate these metal ions from complex mixtures, achieving enrichment and purification of metal ions. For example, in environmental monitoring, it is often necessary to detect the content of heavy metal ions in water samples, soil and other samples.
By adding ethan-1,2-dithiol, a complex can be formed with heavy metal ions, which can then be separated from the sample using extraction, precipitation, and other methods for subsequent analysis and detection. This method has the advantages of easy operation, high selectivity, and good sensitivity. In the fields of trace metal analysis, environmental monitoring, and biological sample analysis, interference from other metal ions often exists.
By adding ethan-1,2-dithiol, stable complexes can be formed with these interfering metal ions, thereby eliminating their interference with the target analyte and improving the accuracy and reliability of the analysis. For example, in atomic absorption spectroscopy analysis, it is often necessary to determine the content of a specific metal ion in the sample. However, there may be spectral interference from other metal ions in the sample. By adding ethan-1,2-dithiol, a complex can be formed with interfering metal ions to reduce their spectral signal, thereby eliminating interference and improving the accuracy of the measurement.
Applications in the field of materials science
Metal organic framework materials (MOFs) are porous crystalline materials composed of metal ions and organic ligands connected by coordination bonds. Ethan-1,2-dithiol can be used as one of the organic ligands to participate in the synthesis of MOFs. By forming stable complexes with metal ions, 1,2-Ethanedithiol can construct MOFs materials with specific pore structures and surface properties.
For example, some MOFs materials have efficient gas adsorption properties and can be used for gas storage and separation; Some MOFs materials have catalytic activity and can be used for catalyzing organic reactions; Some MOFs materials also have sensing properties that can be used to detect harmful substances in the environment. Ethan-1,2-dithiol can also be used for the preparation and modification of metal nanoparticles.
By forming complexes with metal ions, ethan-1,2-dithiol can act as a reducing agent or stabilizer and participate in the synthesis process of metal nanoparticles. During the synthesis process, ethan-1,2-dithiol can control the morphology, size, and dispersion of metal nanoparticles, resulting in metal nanoparticles with specific properties.
Food industry sector
In seasonings, 1,2-ethanedithiol is often used as a fragrance enhancer to enhance the aroma and flavor of seasonings. For example, adding an appropriate amount of ethan-1,2-dithiol to certain seasonings such as soy sauce and vinegar can give them a richer and more unique aroma, thus meeting consumers' requirements for seasoning quality. In meat processing, ethan-1,2-dithiol can simulate the unique flavor of meat, enhancing the taste and quality of meat products.
For example, adding an appropriate amount of ethan-1,2-dithiol to certain meat products such as sausages and ham can give them a richer and more enticing meat aroma, thereby increasing consumers' desire to purchase. In baked goods, ethan-1,2-dithiol is often used as a flavoring additive to give baked goods a unique aroma and flavor. For example, adding an appropriate amount of ethan-1,2-dithiol to certain baked goods such as bread and cakes can give them a more enticing aroma and taste, thereby enhancing the product's market competitiveness.
Other areas
Ethan-1,2-dithiol can undergo specific reactions with biomolecules such as proteins, nucleic acids, etc., forming stable covalent bonds. This characteristic enables ethan-1,2-dithiol to be used for labeling and tracking of biomolecules. By introducing ethan-1,2-dithiol into biomolecules, its unique chemical or physical properties (such as fluorescence, radioactivity, etc.) can be utilized for the detection and localization of biomolecules.
This has important application value in fields such as biological research and drug development. In biochemical research, ethan-1,2-dithiol can also participate in the synthesis of bioactive substances. For example, it can react with certain amino acids or peptide compounds to generate sulfide compounds with specific biological activities. These compounds may have antibacterial, antiviral, anti-tumor and other activities in vivo, providing new candidate substances for drug development.
Ethan-1,2-dithiol can be used as an analytical reagent for the detection and analysis of metal ions. It can selectively form complexes with certain metal ions and indirectly determine the content of metal ions by detecting the formation or changes of complexes. This method has the advantages of high sensitivity and good selectivity, and has important application value in fields such as environmental monitoring and food safety. In the analysis of complex samples, there are often other interfering substances present.
Ethan-1,2-dithiol can be used as a masking agent to form stable complexes with interfering metal ions, thereby eliminating their interference with the target analyte. This can improve the accuracy and reliability of the analysis, ensuring the accuracy of the analysis results. Ethan-1,2-dithiol can also be used as a chromatographic stationary phase. By fixing it on a chromatographic column, the differences in its interactions with different compounds can be utilized to achieve compound separation and purification. This method has important application value in the separation of organic synthesis products, extraction of natural products, and other fields.
The synthesis and preparation process of 1,2-ethyldithiol belongs to the chemical synthesis intermediate in the field of medicine and chemical industry, and its application examples are as follows:
1. To prepare an antimony oxide film, it is mainly to prepare an antimony oxide film by adding 1,2? Add 0.01? Dissolve antimony sulfide in the mixed solution of ethylenediamine and 1,2-ethyldithiol in the proportion of 0.03g antimony sulfide to prepare the electrodeposition liquid.
Then, two transparent electrodes are vertically arranged in an electrolytic cell with electrodeposition liquid to conduct cathodic constant potential electrodeposition with a voltage of 1.5? 8V, plating time 5? After 30 min of electrodeposition, a uniform and dense film was deposited on the cathode.
The membrane electrode was immersed in water for 1? 24 hours, heat treatment at 300 ℃ to 400 ℃ under nitrogen atmosphere for 1, After 10 minutes, it was naturally cooled to room temperature to obtain an antimony oxide film on the conductive substrate. The preparation method is simple, the reaction time is short, and the yield is high. It is suitable for large-scale production in the factory. It is practical and has a good application prospect.
2. Prepare a lysate for peptide resin, which is composed of the following volume percentage components: trifluoroacetic acid (TFA) 85% ~ 90%, 1,2-ethanedithiol (EDT) 0% ~ 10%, water 0% ~ 10%, and anisole (phome) 0% ~ 10%, wherein at least two of the components EDT, water and phome are different and are 0.
In addition, the present invention also discloses a method for preparing somatostatin and the application of the above-mentioned lysate in preparing somatostatin, wherein the above-mentioned lysate is used for cracking reaction.
Through analysis and comparison test, the solid-phase synthetic resin is cleaved by the improved cleavage solution of the invention, which effectively improves the purity of crude peptide and the conversion rate of oxidized peptide, and the oxidation reaction yield is increased by nearly 10%. Therefore, it has obvious economic benefits and can effectively reduce production costs.
I. Background of Early Research on Thiols
The discovery of ethan-1,2-dithiol stemmed from the rapid advancement of organosulfur chemistry in the early 20th century. During that period, chemists expanded the scope of research beyond traditional organic compounds and focused on the structures and properties of sulfur-containing functional groups.
Various thiols and thioethers became major research subjects. Early studies centered on simple alkyl thiols. As synthetic technologies evolved, researchers attempted to prepare ethane derivatives disubstituted with mercapto groups, laying solid theoretical and experimental foundations for the synthesis of ethan-1,2-dithiol.
At that time, primitive synthesis processes and low-purity raw materials led to abundant by-products in sulfur-containing products, which greatly hindered the discovery and purification of such dithiols.
II. First Synthesis and Structural Identification
In the mid-20th century, researchers successfully accomplished the artificial synthesis and structural characterization of ethan-1,2-dithiol. The dominant early synthetic route adopted 1,2-dibromoethane and thiourea as primary raw materials.
An addition reaction firstly produced an isothiouronium salt intermediate, which was then subjected to alkaline hydrolysis and acidification to yield high-purity ethan-1,2-dithiol for the first time.
Later, another synthetic route using alkali metal hydrosulfides to react with haloalkanes was developed, further verifying its molecular structure. Researchers also confirmed its key properties: the ortho arrangement of the two mercapto groups endows the compound with excellent coordination ability and chemical reactivity. Since then, ethan-1,2-dithiol has been formally classified into the family of organosulfur compounds.
III. Synthesis Process Iteration and Popularization of Research
Following its initial synthesis, research on ethan-1,2-dithiol entered a stage of process optimization. The original synthetic methods suffered from excessive by-products and low yields, failing to meet experimental requirements.
Subsequent researchers adopted high-pressure reaction control and raw material ratio optimization to drastically reduce polymeric by-products and improve synthetic efficiency. With mature manufacturing techniques, the compound was no longer limited to niche laboratory research and gradually became an essential reagent in organic synthesis and metal coordination chemistry.
Benefiting from its unique dimercapto structure, it can effectively chelate metal ions and participate in the construction of complex molecules, achieving routine application in laboratories. It also promoted the systematic research and development of polythiol compounds.
Main Synthetic Process
The thiourea method is the most widely used technique in laboratories and industrial production, with 1,2-dibromoethane and thiourea as the primary raw materials. The mixture is heated to reflux in an ethanol system, where a nucleophilic substitution reaction takes place to produce a solid isothiouronium salt intermediate. A strong alkali such as sodium hydroxide is then added for alkaline hydrolysis, which decomposes the intermediate and releases thiol components. The pH of the system is subsequently adjusted with acid solution.
Air must be excluded throughout the reaction to avoid oxidation of mercapto groups. The crude product is separated via liquid-liquid extraction and washing, then purified by vacuum distillation. This process features stable reactions, few side reactions and high product purity, making it the dominant preparation route.
Other Synthetic Routes
Another approach involves the reaction between haloalkanes and hydrosulfides. 1,2-dichloroethane reacts with sodium hydrosulfide in a polar solvent. This method has mild reaction conditions and lower costs, yet the raw materials exhibit low reactivity, leading to a lower overall yield compared with the thiourea method.
There is also a hydrogen sulfide addition process, which demands high equipment tightness and is mainly applied for custom production. For all the above processes, distillation is adopted to remove impurities and obtain qualified ethan-1,2-dithiol final products.
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