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1,2,4-Triazole (CAS number 288-88-0) is a five membered nitrogen-containing heterocyclic compound composed of two carbon atoms and three nitrogen atoms, with the molecular formula C2H3N3 CAS 288-88-0 and a molecular weight of 69.07. Its chemical structure exhibits a coplanar characteristic, with both C-N and N-N bond lengths ranging from 132-136pm, consistent with aromatic compounds, and there are two tautomers, among which the 1H-1,2,4-triazole form is more stable. This compound is a white needle shaped crystal with a melting point of 120-121 ℃ and a boiling point of 260 ℃ (decomposition). It is easily soluble in water (with a solubility of 1250g/L at 20 ℃), slightly soluble in ethyl acetate, and insoluble in non-polar solvents such as benzene.
As an important organic intermediate, it holds a core position in the pharmaceutical field. Its unique dipole effect, hydrogen bonding ability, and rigid structure make it the preferred backbone for drug development, commonly found in clinical drugs such as antifungal drugs (such as fluconazole and itraconazole), anticancer drugs (such as VEGFR-2 kinase inhibitors), antiviral drugs (such as hepatitis C virus inhibitors), anticonvulsants, and anti anxiety drugs. According to statistics, there are about 15 drugs containing this structure on the market worldwide, and more than 50 candidate drugs are in the research and development stage.
In the field of pesticides, it is a key raw material for the synthesis of triazole fungicides (such as triazolone and tebuconazole) and plant growth regulators (such as paclobutrazol and tebuconazole). Its derivatives achieve efficient and low toxicity pest control by inhibiting the synthesis of ergosterol by pathogenic bacteria or regulating plant hormone balance. In addition, the compound is also used in the manufacturing of dyes, rubber additives, and optoelectronic materials. Its metal complexes exhibit special functions in catalysis, corrosion inhibitors, and ionic liquids. With the increasing demand for new drug development and green agriculture, the market demand continues to expand, becoming one of the important basic raw materials in the chemical industry.
|
Chemical Formula |
C2H3N3 |
|
Exact Mass |
69 |
|
Molecular Weight |
69 |
|
m/z |
69 (100.0%), 70 (2.2%), 70 (1.1%) |
|
Elemental Analysis |
C, 34.78; H, 4.38; N, 60.84 |
1,2,4-triazole (CAS number 288-88-0) is a five membered nitrogen-containing heterocyclic compound composed of two carbon atoms and three nitrogen atoms. It is easily soluble in water (with a solubility of 1250g/L at 20 ℃), slightly soluble in ethyl acetate, and insoluble in non-polar solvents such as benzene. Thanks to its unique chemical properties, pyrrodiazol has demonstrated extensive application value in various fields such as pharmaceuticals, pesticides, dyes, rubber additives, optoelectronic materials, and functional materials.
It is an important intermediate in the pharmaceutical field, and its unique dipole interaction, hydrogen bonding ability, and rigid structure make it the preferred backbone for drug development. Its derivatives can regulate enzyme activity, inhibit cell proliferation, or interfere with virus replication by binding with high affinity to biological receptors, thereby exerting therapeutic effects.
1. Antifungal drugs
Fluconazole is a typical application case of this substance. As a triazole antifungal drug, fluconazole has significant therapeutic effects on deep fungal infections such as Candida albicans and Cryptococcus neoformans by competitively inhibiting the synthesis of ergosterol in fungi.
It has a wide spectrum of antifungal activity, low liver toxicity, good oral absorption, and high bioavailability, and has been designated by the World Health Organization (WHO) as the preferred drug for treating systemic fungal infections. As a key intermediate of fluconazole, it directly determines the biological activity of the drug by participating in the construction of its molecular skeleton.
2. Anti cancer drugs
Pyrrodiazol derivatives exhibit multiple mechanisms of action in the field of anti-cancer, including enzyme inhibition, microtubule protein regulation, and angiogenesis inhibition. For example:
VEGFR-2 kinase inhibitor: Compound 2 (1,2,4-triazolone derivative) exhibits significant cytotoxicity against HT-29 (human colon cancer), H460 (human lung cancer), A549 (human lung cancer), and MKN-45 (human gastric cancer) cell lines, with IC50 values of 0.08, 0.14, 0.11, and 0.031 mM, respectively. Structure activity relationship studies have shown that introducing electron withdrawing groups on the terminal benzene ring can enhance anti-tumor activity.
Tubulin modulator: Compound 3a (triazole quinoxaline derivative) has IC50 values of 1.65, 3.61 and 8.58 mM respectively on MCF-7 (human breast cancer), HCT-116 (human colon cancer) and HepG2 (human liver cancer) cell lines, which plays an anti-cancer role by inhibiting tubulin polymerization.
3. Antiviral drugs
Pyrrodiazol derivatives can exert antiviral effects by interfering with the virus replication cycle or inhibiting the activity of key viral enzymes. For example:
HSV-1 inhibitor: Compound 5a (2- (3-mercapto-5-amino-1H-1,2,4-triazole) ethyl acetate derivative) can reduce herpes simplex virus type 1 (HSV-1) plaques on African green monkey kidney cells by 50% at a dose of 80 mM, and binds to the active site of HSV-1 thymidine kinase through hydrogen bonding.
HCMV inhibitor: Compound 5b (quinoxaline derivative) has an IC50 value of less than 0.05 mM against human cytomegalovirus (HCMV) and exerts antiviral effects by inhibiting viral DNA replication.
4. Anticonvulsant and anti anxiety drugs
1,2,4-Triazole derivatives can inhibit epileptic seizures by regulating voltage-gated ion channels or gamma aminobutyric acid neuron activity. For example:
Compound 4a exhibited an ED50 value of 19.7 mg/kg and a protective index (PI) value of 34.8 in the electric shock test (MES), exerting anticonvulsant effects by inhibiting voltage-gated sodium channels.
Compound 4b (triazole purine derivative) exhibited significant anticonvulsant activity in both MES and scPTZ (subcutaneous injection of pentazolium) models, with an ED50 value of 23.4 mg/kg and a PI value greater than 25.6.
5. Other drugs
It is also widely used in the research and development of antidepressants, skeletal muscle relaxants, anti migraine drugs, antiplatelet drugs, and aromatase inhibitors. For example, 3-amino-1,2,4-triazole is an intermediate in the synthesis of the coronary heart disease drug tramadol, which is used to treat angina and myocardial infarction by antagonizing platelet-derived growth factor (PDGF).
It is a key intermediate for synthesizing triazole fungicides and plant growth regulators. Its derivatives achieve efficient and low toxicity pest control by inhibiting the synthesis of ergosterol by pathogenic bacteria or regulating plant hormone balance.
1. Triazole fungicides
It can synthesize triazole fungicides such as triadimefon, triazolone, triazole alcohol, tebuconazole, pichlorotriazole alcohol, enoconazole, tebuconazole, hexanazol alcohol, cycloazol alcohol, propiconazole, fluorosilazole, triflurazole, fipronil, carbendazole, fluoether azole, hydroxymyclobutrazol, fipronil azole, fipronil azole, etc. These fungicides have significant control effects on various fungal diseases such as powdery mildew, rust, and anthracnose, and have low toxicity to crops and the environment, which meets the needs of green agriculture development.
2. Plant growth regulators
Plant growth regulators such as paclobutrazol, enoconazole, and metronidazole can be synthesized to control excessive crop growth, promote branching, and enhance stress resistance by inhibiting gibberellin synthesis or regulating cytokinin activity. For example, paclobutrazol is widely used in crops such as rice and wheat, which can significantly improve yield and quality.
3. Pesticides and herbicides
Pyrrodiazol derivatives can also be used for the synthesis of insecticides (such as tin triazole) and herbicides (such as 3-amino-1,2,4-triazole). Among them, 3-amino-pyrrodiazol, as a non selective herbicide, is particularly suitable for cotton defoliation treatment, but its application scope is gradually limited due to its environmental toxicity.
1. Dye intermediates
Can be used as an intermediate in dye synthesis to participate in the construction of structures such as azo dyes and anthraquinone dyes. Its nitrogen atom can form a conjugated system with the aromatic ring in the dye molecule, enhancing the color brightness and fastness of the dye.
2. Rubber additives
Pyrrodiazol and its derivatives can be used as rubber vulcanization accelerators or anti-aging agents to improve the physical properties and durability of rubber products by adjusting the vulcanization reaction rate or inhibiting oxidative degradation. For example, 1,2,4-triazole-3-carboxylic acid ester compounds can be used as efficient vulcanization accelerators and are widely used in the production of rubber products such as tires and seals.
Exploration of Emerging Applications in the Field of Optoelectronic Materials and Functional Materials
1. Photoconductor materials
Photoconductors that can be used for replication systems, their derivatives enhance photoelectric conversion efficiency by adjusting electron transfer performance or light absorption characteristics. For example, 1,2,4-triazole based complexes exhibit excellent carrier mobility in organic optoelectronic materials and can be used to prepare efficient organic solar cells.
2. Conductive materials
Pyrrodiazol derivatives can form conductive polymers by coordinating with metal ions, or serve as dopants to regulate the conductivity of semiconductor materials. For example, the copper-1,2,4-triazole complex has a one-dimensional chain structure and exhibits good conductivity and magnetism, which can be used to prepare molecular wires or magnetic storage materials.
3. Supramolecular materials
Supramolecular assemblies can be constructed through non covalent forces such as hydrogen bonding and π - π stacking, achieving functions such as drug controlled release, molecular recognition, or catalysis. For example, pyrrodiazol based supramolecular gel can achieve controlled drug release through light response or pH response, providing new ideas for intelligent drug delivery systems.
Other fields: Expansion of diversified applications
1. Catalyst
1,2,4-triazole and its derivatives can serve as catalysts for organic synthesis, improving reaction efficiency by stabilizing transition states or activating reactants. For example, 1,2,4-triazole based copper complexes can catalyze the epoxidation of olefins with high selectivity and activity.
2. Analytical reagents
Can be used for complexometric titration or colorimetric analysis of metal ions. For example, its complex with copper ions has characteristic absorption peaks at specific wavelengths, which can be used for quantitative detection of copper ions.
3. Corrosion inhibitors
1,2,4-triazole derivatives can form a protective film on metal surfaces, inhibiting the corrosion of corrosive media. For example, 1,2,4-triazole-5-carboxylic acid can serve as a corrosion inhibitor for copper, exhibiting excellent protective effects in acidic environments.
Hydrazine hydrate was gradually added into methylamine to directly synthesize 1,2,4-triazole .
60kg methylamine is first heated to 175-85C, and then slowly added with 30kg 80% hydrated fat. After dripping, heating and dehydration, the mixture is kept at 180-85C for 30min to obtain trinitrogen with a yield of 91%
This process is one of the commonly used methods for producing Sanzawa at present. The advantages are that the raw materials are simple and easy to obtain, the production process is simple, the equipment requirements are not high, and the product yield is high. However, compared with the formic acid method, the price of methamphetamine is higher than that of formic acid dumpling, and the unreacted methamphetamine in the product is not easy to separate from the product. At present, there are two methods to separate methylenediamine from trimethylenediamine. One is to use high vacuum distillation, which can recover methylamine. However, because the boiling point of methylamine is as high as 210C, it is difficult to achieve such high vacuum distillation in production, so this scheme is only of laboratory significance; The second is that the decomposition of trimethylamine at 210C is not complete and will cause the side reaction of trimethylamine, which will reduce the product content and yield. Therefore, how to effectively separate methylamine at low cost is a problem to be solved by this method. Hydration first reacts with methylamine to form monomethyl and drops into methyl to synthesize azoles.
100 g of 80% hydrating tillage is added to 100 g of methylamine at 90 ℃, and the temperature is kept at 90 ℃ for 8 hours after dropping,. At 175-85C, add 100g of the reaction liquid drop to the reaction liquid drop, add the dehydration drop while heating, and keep it for 30min. The yield is 90%.
This method has no practical significance in production, but it has confirmed that the synthesis of triazine by methylamine and hydration method is carried out step by step. The first step is the reaction of methylamine and equimolar hydration to form A, and then to form three with another 1mol of A. The temperature required for the first reaction is not high, while the closed loop requires high temperature. Therefore, hydration must be added slowly to keep the reactants at high temperature.
Put ammonia into 130g 85% formic acid, and when the temperature of the reactant rises to 130 CpH=7-8, the ammonia injection will end. When the temperature rises to 155C and 80% 59g is added for 23h, the water is added for 3h, and then the temperature rises to 210 C, 75g of nitrogen trioxide is obtained. The yield is 9108% 121. The method A is also one of the three commonly used methods for production at present. 1,2,4-Triazole has the advantages of low raw material price, high quality and yield, and low raw material cost. However, the production process of formic acid process is higher than that of complex acid process of formic acid process. The maintenance cost of equipment is higher than that of formic acid process. After the completion of formic acid process, it must be heated to 155C for dehydration and dehydration, which consumes more energy. Therefore, the comprehensive cost of formic acid method has no obvious advantage compared with methylamine method. However, manufacturers with by-product formic acid have obvious cost advantages in producing trinitrogen by formic acid method. For example, Huang Ciyou and others use the by-product formic acid in the production of tricyclic acid to form three 85%.
Add 695g 72% water drops into 92g formic acid and react for 10min at 80C. Then drop the above reaction solution into 175-185C methylamine and dehydrate it for 30min. The yield of trinitrogen is 95.8%! This process combines the advantages of methylamine method and formic acid method. The amount of formic acid is only half of that of formic acid method. The only way to use the first method is not to inject ammonia, so the cost of raw materials is lower. No gas is introduced and tail gas ammonia is absorbed. The production process is simpler than that of formic acid method. It is a method worth adopting at present, but the corrosivity of formic acid still exists.
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