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3-hydroxytetrahydrofuran(3-HTF) belongs to the fine chemical product, with the molecular formula C4H8O2, CAS 453-20-3, molecular weight 88.1051, density 1.148g/cm3, and irritation. According to chirality, it can be divided into (S) -3-HTF and (R) -3-HTF. Among them, (S) -3-HTF is a common 3-HTF product on the market. As an important pharmaceutical intermediate, it is widely used in the synthesis of anticancer drugs, hypoglycemic drugs, anti AIDS and other drugs. As a pharmaceutical intermediate, it can be used in the synthesis of alfatinib (for the treatment of advanced non-small cell lung cancer and her2 positive advanced breast cancer), engegliptin (a hypoglycemic drug), apnavir (a drug for the treatment of AIDS), and foshanavir calcium (both directly used in the treatment of AIDS and as a precursor drug for the synthesis of apnavir), and other medicines. In addition, 3-HTF can also be used to synthesize pesticides, which can improve the herbicidal activity and selectivity of diphenyl ether herbicides.
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Chemical Formula |
C4H8O2 |
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Exact Mass |
88 |
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Molecular Weight |
88 |
|
m/z |
88 (100.0%), 89 (4.3%) |
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Elemental Analysis |
C, 54.53; H, 9.15; O, 36.32 |
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3-Hydroxytetrahydrofuran (3-HTF) is an organic compound with a wide range of applications.
1. Drug synthesis:
3-HTF can be used as an intermediate in the synthesis of many drugs. For example, it can be used to synthesize anti epileptic drugs and other central nervous system related drugs.
2. Sustainable energy and fuels:
3-HTF can be used as a raw material for renewable energy and sustainable fuels. By hydrogen hydrolysis reaction, 3-HTF can be converted into hydrogen and ethylene glycol, which can be used for fuel cells and other energy applications.
3. Solvent:
Due to its good solubility and low toxicity, 3-HTF can be used as a solvent. It can be used to dissolve certain organic compounds, coatings, and resins. In addition, due to its low volatility, 3-HTF can be used as a substitute in some special industrial applications.
4. Polymer materials:
3-HTF can be used as a monomer for polymer synthesis. It can undergo polymerization reactions with other monomers to form polymer materials with specific functions and properties. These materials can be applied in plastics, coatings, fibers, and adhesives.
5. Agricultural Chemicals:
3-HTF can be used to synthesize agricultural chemicals such as insecticides and herbicides. These chemicals help protect crops from pests and diseases, and improve crop yield and quality.
6. Surfactants:
3-HTF can be used as a raw material for surfactants. It can react with other compounds to form surfactants with good emulsifying, dispersing, and stabilizing properties. These surfactants are widely used in fields such as pharmaceuticals, cosmetics, detergents, and personal care products.
7. Chemical analysis:
3-HTF can be used as an internal standard substance for gas chromatography analysis. It can be used for quantitative analysis to help determine and detect the presence and concentration of other compounds.
8. Other applications:
3-HTF can also be used for synthesizing liquid crystal materials, preservatives, dye intermediates, spices, and food additives. In addition, it is also used in some special fields, such as optical materials, electronic devices, and biomedical engineering.
The hydrolysis synthesis method of 3-Hydroxytetrahydrofuran with epoxy acetone is as follows:
Step:
Epoxy acetone+H2O → C4H8O2
1. Prepare epoxy acetone and aqueous solution.
2. Dissolve epoxy acetone in an appropriate solvent (such as ethanol or dimethylformamide) to prepare a solution of approximately 0.1-0.5 M.
3. Slowly add water to the epoxy acetone solution, usually dropwise. Stirring should be maintained during the reaction process.
4. Continue stirring the reaction mixture at room temperature for a period of time (usually several hours to several days) to fully hydrolyze epoxy acetone to produce.
5. After the reaction is completed, the obtained 3-HTF product is separated and purified from the reaction mixture by distillation or other appropriate extraction methods.
3-HTF γ- The hydroxyl ketone reduction method is as follows:
γ- Hydroxyl ketone+reducing agent → C4H8O2
Step:
1. Preparation γ- Hydroxyl ketone and reducing agent solution.
2. Add γ- Hydroxy ketones are dissolved in appropriate solvents, such as ethanol or dimethylformamide, and prepared into a solution of appropriate concentration.
3. To γ- Add a suitable reducing agent to the hydroxyl ketone solution, the commonly used reducing agent is sodium borohydride (NaBH4), and the amount added should be adjusted according to the specific molar ratio of the reactant.
4. The reaction mixture usually requires a longer reaction time. React at room temperature and continue stirring for several hours to several days to ensure sufficient reaction.
After the reaction is completed, the required 3-HTF product can be purified from the reaction mixture by distillation, extraction, or other appropriate methods.
The ethyl acetate hydrolysis method for it is as follows:
C4H8O2+H2O → C4H8O2+C2H4O2
Step:
1. Prepare ethyl acetate and aqueous solution.
2. Dissolve ethyl acetate in an appropriate solvent, such as ethanol or dimethylformamide, and prepare a solution of approximately 0.1-0.5 M.
3. Slowly add water to the ethyl acetate solution, usually dropwise. Stirring should be maintained during the reaction process.
4. Continue stirring the reaction mixture at room temperature for a period of time (usually several hours to several days) to fully hydrolyze ethyl acetate to produce.
5. After the reaction is completed, the obtained product is separated and purified from the reaction mixture by distillation or other appropriate extraction methods.
The isoamyl alcohol esterification method of it is as follows:
C4H8O2+C5H12O → C4H8O2 isoamyl ester+H2O
Step:
1. Prepare a 3-Hydroxytetrahydrofuran and isoamyl alcohol solution.
2. Dissolve 3-HTF in an appropriate solvent, such as dimethylformamide or tetrahydrofuran, and prepare a solution of appropriate concentration.
3. Add an appropriate amount of catalyst, commonly used as an acidic catalyst, such as sulfuric acid or p-toluenesulfonic acid, to the 3-HTF solution. The addition amount should be adjusted according to the specific molar ratio of reactants.
4. Add isoamyl alcohol to the reaction mixture. Isoamyl alcohol is the alcohol part of the esterification reaction, and its addition amount should also match the molar ratio of 3-HTF.
5. The reaction mixture usually needs to be stirred at room temperature for several hours to several days to ensure sufficient reaction.
After the reaction is completed, the required 3-HTF esterification products can be purified from the reaction mixture by distillation, extraction, or other appropriate methods.
Adverse reactions
3-hydroxytetrahydrofuran is an important organic compound with wide applications in various fields such as chemical synthesis, pharmaceutical manufacturing, and fragrance industry. In chemical synthesis, it often participates as an intermediate in the construction of various complex organic molecules; In the field of medicine, some drug molecules contain 3-hydroxytetrahydrofuran groups in their structure, which play an important role in the treatment of diseases; In the spice industry, it can be used to synthesize spice components with unique aromas. However, like many chemicals, 3-hydroxytetrahydrofuran may also cause some adverse reactions during use, which may not only affect the health of users but also pose a certain harm to the environment.
Acute toxic reaction
Through acute toxicity experiments on experimental animals such as mice and rats, it was found that 3-hydroxytetrahydrofuran has certain acute toxicity. At a certain dose, animals will experience a series of toxic symptoms. For example, after oral administration of high doses of 3-hydroxytetrahydrofuran to mice, symptoms such as reduced activity, mental fatigue, and shortness of breath may occur in a short period of time. With increasing dosage, seizures, coma, and even death may also occur. After inhaling high concentrations of 3-hydroxytetrahydrofuran vapor, rats may experience symptoms such as eye irritation, tearing, coughing, and difficulty breathing. In severe cases, it can lead to respiratory failure and death.
Chronic toxic reactions
Long term exposure to low-dose 3-hydroxytetrahydrofuran may have chronic toxic effects on multiple organs and systems in the human body. Animal experiments have shown that long-term intake of feed containing 3-hydroxytetrahydrofuran in rats can cause varying degrees of liver and kidney damage. The liver shows swelling, degeneration, and even necrosis and fibrosis of liver cells; The kidneys may experience changes such as damage to renal tubular epithelial cells and interstitial fibrosis. In addition, long-term exposure may also affect the immune system of animals, leading to a decline in immune function and making them more susceptible to various diseases. For personnel engaged in long-term work related to 3-hydroxytetrahydrofuran, such as chemical production workers, laboratory researchers, etc., improper protective measures and long-term exposure to environments containing 3-hydroxytetrahydrofuran may cause chronic toxic effects on the human body.
Irritation to the skin and mucous membranes
3-Hydroxytetrahydrofuran has a certain degree of irritation, and when the skin comes into direct contact with the substance, it may cause skin irritation symptoms. Mild contact may cause discomfort such as redness, itching, and stinging of the skin; If the contact time is long or the concentration is high, serious symptoms such as skin burns, blisters, ulcers, etc. may occur. For example, in the process of chemical production, if workers accidentally splash 3-hydroxytetrahydrofuran on the skin, they should immediately rinse with plenty of water and seek medical treatment in a timely manner, otherwise it may aggravate skin damage. Mucosal tissues such as eyes, nasal cavity, and oral cavity are more sensitive to 3-hydroxytetrahydrofuran. When these mucous membranes come into contact with 3-hydroxytetrahydrofuran, they immediately produce a strong irritant response. Eye contact can cause symptoms such as eye pain, tearing, photophobia, and conjunctival congestion. In severe cases, it may lead to corneal damage and affect vision; After contact between the nasal cavity and oral mucosa, discomfort symptoms such as sneezing, runny nose, coughing, and redness and swelling of the oral mucosa may occur.
Damage to the respiratory system
3-hydroxytetrahydrofuran is volatile and its vapor can be inhaled by the human body. Inhaling low concentrations of 3-hydroxytetrahydrofuran vapor may cause respiratory irritation symptoms such as coughing, sputum production, and wheezing. Long term inhalation of low concentration vapor or short-term inhalation of high concentration vapor may cause more serious damage to the respiratory system. For example, it can cause bronchospasm, pulmonary edema, etc., affecting the gas exchange function of the lungs, causing patients to experience symptoms such as difficulty breathing and cyanosis, and in severe cases, even endangering their lives. Animal experiments and some clinical observations have found that inhalation of 3-hydroxytetrahydrofuran can cause pathological changes in lung tissue. Under a microscope, changes such as thickening of alveolar walls and infiltration of inflammatory cells in the lung interstitium can be observed, which can affect the normal structure and function of the lungs, leading to a decline in respiratory function.
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