2-Chloro-5-chloromethyl Thiazole (CAS#105827-91-6)

2-Chloro-5-chloromethyl thiazole, with the CAS number 105827-91-6, is an important chemical intermediate in the field of organic synthesis. Its chemical formula is \(C_{4}H_{3}Cl_{2}NS\), and the molecular weight is approximately 168.04 g/mol. This compound consists of a thiazole ring, which is a five - membered heterocyclic ring containing both a sulfur and a nitrogen atom, with a chlorine atom at the 2 - position and a chloromethyl group at the 5 - position. The unique structure of 2-chloro-5-chloromethyl thiazole endows it with special chemical reactivity, making it a key building block for the synthesis of a variety of complex organic compounds, especially in the agrochemical and pharmaceutical industries.

2.1 Appearance

2-Chloro-5-chloromethyl thiazole is usually a colorless to light yellow liquid at room temperature. Its clear and transparent liquid state allows for easy handling and mixing in chemical reactions. This physical form also makes it convenient for measuring accurate volumes during the synthesis process.

2.2 Solubility

It has certain solubility characteristics. It is soluble in many organic solvents such as ethanol, acetone, and dichloromethane. This solubility property is crucial as it enables the compound to participate in various chemical reactions carried out in organic solvent media. For example, in the synthesis of pesticides, the reaction often takes place in an organic solvent system, and the good solubility of 2-chloro-5-chloromethyl thiazole ensures its homogeneous distribution in the reaction mixture, facilitating efficient reaction progress.

2.3 Stability

Under normal storage conditions, 2-chloro-5-chloromethyl thiazole is relatively stable. However, it should be stored away from strong oxidizing agents, strong acids, and bases to prevent unwanted chemical reactions. Exposure to extreme temperatures or light for an extended period may also affect its stability. Proper storage in a cool, dry, and dark place can maintain its quality and reactivity for a long time.

3.1 Agrochemical Industry

3.1.1 Application

2-Chloro-5-chloromethyl thiazole is widely used as an intermediate in the production of pesticides. Pesticides play a vital role in modern agriculture by protecting crops from various pests, diseases, and weeds, thereby ensuring high crop yields and food quality. As an intermediate, 2-chloro-5-chloromethyl thiazole is used to synthesize a series of highly effective pesticides.

3.1.2 Mechanism of Action

The pesticides synthesized from 2-chloro-5-chloromethyl thiazole often act on the nervous systems of pests. For example, some of these pesticides can inhibit the activity of acetylcholinesterase in pests. Acetylcholinesterase is an enzyme that is essential for the normal functioning of the nervous system. When acetylcholinesterase is inhibited, acetylcholine, a neurotransmitter, accumulates in the synaptic cleft. This accumulation disrupts the normal transmission of nerve impulses in the pest's body, leading to paralysis and eventually death of the pest. In addition, some pesticides synthesized from this intermediate can also act on other key physiological processes in pests, such as energy metabolism and cell membrane function, further enhancing their pesticidal effects.

3.2 Pharmaceutical Industry

Although its main application is in the agrochemical field, 2-chloro-5-chloromethyl thiazole also shows potential in the pharmaceutical industry. It can be used as a starting material for the synthesis of some heterocyclic - containing drugs. The thiazole ring in its structure is a common structural motif in many bioactive molecules. In drug synthesis, the unique reactivity of the chlorine atoms and the thiazole ring can be exploited to construct more complex molecular structures with specific biological activities. For example, it can be used to synthesize drugs that target certain enzymes or receptors in the human body, which may have applications in the treatment of various diseases such as antibacterial, antifungal, and anti - inflammatory therapies.

4.1 Imidacloprid - related Pesticides

2-Chloro-5-chloromethyl thiazole is an important intermediate in the synthesis of imidacloprid - related pesticides. Imidacloprid is a widely used neonicotinoid insecticide. The synthesis of imidacloprid involves a series of chemical reactions starting from 2-chloro-5-chloromethyl thiazole. Through reactions such as substitution and condensation, the structure of 2-chloro-5-chloromethyl thiazole is gradually transformed into the characteristic structure of imidacloprid. Imidacloprid - based pesticides have high efficiency in controlling a wide range of sucking pests such as aphids, whiteflies, and leafhoppers. They are systemic insecticides, which means that they can be absorbed by plants and transported within the plant tissues, providing long - term protection to the crops.

4.2 Thiamethoxam - related Pesticides

It is also used in the production of thiamethoxam - related pesticides. Thiamethoxam is another member of the neonicotinoid insecticide family. 2-Chloro-5-chloromethyl thiazole participates in the key steps of thiamethoxam synthesis. Thiamethoxam has excellent activity against soil - dwelling pests and foliar - feeding insects. It has a fast - acting and long - lasting effect, and can effectively protect crops from pest damage throughout the growth cycle.

4.3 Other Pesticides

In addition to imidacloprid and thiamethoxam, 2-chloro-5-chloromethyl thiazole can be used as an intermediate for the synthesis of other pesticides with different chemical structures and pesticidal mechanisms. These pesticides may have specific activities against certain pests or diseases, and can be used in combination with other pesticides to form a comprehensive pest control system in modern agriculture.

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