Shaanxi BLOOM Tech Co., Ltd. is one of the most experienced manufacturers and suppliers of 2-chloro-5-chloromethylpyridine (ccmp) cas 70258-18-3 in China. Welcome to wholesale bulk high quality 2-chloro-5-chloromethylpyridine (ccmp) cas 70258-18-3 for sale here from our factory. Good service and reasonable price are available.
2-chloro-5-chloromethylpyridine (CCMP), white crystal, is an organic compound and an important intermediate in the synthesis of pesticides and medicine. Industrial products with strong sensitization are orange-red viscous liquid, with a pungent smell, soluble in a variety of organic solvents and organic acids. Store in a sealed container in a cool, dry place. The storage area must be locked and the keys must be kept by technical experts and their assistants. Storage must be kept away from oxidants. It is used as an intermediate of pesticide imidacloprid and acetamiprid; 2-chloro-5-chloromethylpyridine is an intermediate of insecticides imidacloprid and acetamiprid.
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Chemical Formula |
C6H5Cl2N |
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Exact Mass |
161 |
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Molecular Weight |
162 |
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m/z |
161 (100.0%), 163 (63.9%), 165 (10.2%), 162 (6.5%), 164 (4.1%) |
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Elemental Analysis |
C, 44.48; H, 3.11; Cl, 43.76; N, 8.65 |
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Melting point 37-42 ° C (lit.), Boiling point 267.08 ° C (rough estimate), Density 1.4411 (rough estimate), Refractive index 1.6000 (estimated), Flash point > 230 ° f, Storage condition: insert atmosphere, 2-8 ° C, Acidity coefficient (PKA) - 0.75 ± 0.10 (predicted), Form moist crystals, Color beige, Solubility in water, BRN 1635690, InChIKeySKCNYHLTRZIINA-UHFFFAOYSA-N.
This molecule is composed of a pyridine ring and a chloroethane group. On the pyridine ring, there is a chlorine atom (Cl) connected to the second carbon atom, while in the chloroethane group, there is a chlorine atom (Cl) connected to the carbon atom, and a methyl group (CH3) connected to the same carbon atom.
Now let's conduct a more detailed analysis:
Pyridine ring: A pyridine ring is a six membered heterocyclic ring composed of six carbon atoms and one nitrogen atom. In this molecule, the nitrogen atom is located at the center position. The carbon atoms on the pyridine ring can be numbered from 1 to 6, where the first carbon atom is connected to the nitrogen atom.
2nd carbon atom: The 2nd carbon atom is the carbon atom connected to the chlorine atom on the pyridine ring. It is connected to carbon atom 1 through a carbon nitrogen single bond.
Chloroethane group: The chloroethane group is composed of a chlorine atom and a methyl group. The chlorine atom is connected to the carbon atom of the chloroethane group, and the methyl group is connected to the same carbon atom. This chloroethane group can be regarded as a chloroethane molecule.
The specific steps for the synthesis of 2-chloro-5-chloromethylpyridine (CCMP) in the laboratory are as follows:
Mix 2-chloro-5-methylpyridine with an appropriate amount of sodium hydroxide solution in a round bottom flask and heat to 100 ℃.
C6H6ClN + NaOH → 2−Cl−5−Py + MeOH
The product obtained in the previous step is reacted with sulfuric acid to undergo sulfation.
2−Cl−5−Py + H2SO4 → 2−Cl−5−ClMPy + H2O
The obtained product is extracted and crystallized, and then recrystallized for purification.
2−Cl−5−ClMPy+ H2O → 2−Cl−5−ClMPy−H2O
2−Cl−5−ClMPy + H2O → 2−Cl−5−ClMPy + H2O
Dry the purified product to obtain the final product.
2−Cl−5−ClMPy → 2−Cl−5−ClMPy + H2O → 2−Cl−5−ClMPy
Add 2-chloro-5-methylpyridine and an appropriate amount of sodium hydroxide solution to a round bottom flask and stir evenly.
Place the round bottomed flask in a rotary evaporator, heat it in an oil bath to 100 ℃, and hold for several hours to allow complete reaction of 2-chloro-5-methylpyridine.
After the reaction is completed, pour the reaction solution into a separating funnel and add an appropriate amount of water for extraction. After layering, separate the organic phase from the aqueous phase.
Dry the organic phase through a silicone dryer to remove moisture and impurities.
Pour the dried organic phase into a beaker, add an appropriate amount of sulfuric acid, and stir evenly. Then place it in an ice water bath to cool and allow it to crystallize.
After the crystallization is complete, filter the crystals and wash with a small amount of cold water. Dry the crystals in an oven to obtain the final product, 2-chloro-5-chloromethylpyridine.
Product purification
Place the obtained 2-chloro-5-chloromethylpyridine in a weighing bottle, weigh and record.
Dissolve the 2-chloro-5-chloromethylpyridine in the weighing bottle with an appropriate amount of dichloromethane, and then perform column chromatography purification with silica gel.
Recrystallize the purified 2-chloro-5-chloromethylpyridine for further purification.
Dry the purified 2-chloro-5-chloromethylpyridine to obtain the final product.
The process of cyclization of acetaldehyde to synthesize 2-chloro-5-methylpyridine actually involves multiple chemical reactions. The following are the detailed steps and corresponding chemical equations for these reactions:
This is obtained through nitrification reaction. Under the action of nitric acid, the C-5 position of 3-methylpyridine is nitrated, producing N-oxide of 2-chloro-5-methylpyridine.
3−MePy + HNO3 → 2−Cl−5−MePyNO2 + HNO2
This reaction is a condensation reaction between pyrimidine and acetaldehyde catalyzed by acid, forming a five membered ring.
C4H4N2 + C3H6CHO → 2−Cl−5−MePy + H2O
This is a typical electrophilic substitution reaction. Chlorine, as an electrophilic reagent, attacks the C-2 position in 2-chloro-5-methylpyridine to generate 2,5-dichloromethylpyridine.
2−Cl−5−MePy + Cl2 → 2,5−Cl2MePy
Continue chlorinating 2,5-dichloromethylpyridine, replacing the chlorine at position C-5 to generate 2,3,5-trichloromethylpyridine.
2,5-Cl2MePy + Cl2 → 2,3,5-Cl3MePy
This is a liquid-phase reaction that involves the action of a solvent and azodiisocitrile as the initiator. The specific chemical equation needs to be determined based on specific experimental conditions and operations, but can be roughly expressed as: 2,3,5−Cl3MePy+RCOCl → 2−Cl− (RCO) MePy
Among them, R=CCl4 or C18H37.
These steps provide a method for synthesizing the target compound 2-chloro-5-chloromethylpyridine (CCMP) from basic raw materials. However, these reactions may need to be carried out under specific conditions and may involve other intermediate steps or side reactions. Therefore, before actual operation, it is recommended to conduct detailed literature research and experimental pre research.
2-chloro-5-chloromethylpyridine (CCMP, chemical formula C ₆ H ₅ Cl ₂ N) is an important pyridine organic intermediate that occupies a central position in modern pesticide chemistry. As a key synthetic precursor for new nicotine insecticides such as imidacloprid and imidacloprid, the industrial production of CCMP directly promoted the innovation of global insecticide technology at the end of the 20th century.
At the end of the 19th century, the rise of pyridine chemistry laid the chemical foundation for CCMP.
In 1876, Scottish chemist Thomas Anderson first isolated pyridine from bone tar, and then German chemist Adolf von Baeyer systematically studied the substitution reaction of pyridine.
At the beginning of the 20th century, with the establishment of key pyridine synthesis methods such as the Chichibu Babin reaction, the synthesis of chlorinated pyridine derivatives became possible.
In the 1930s, researchers from the German company IG Farben first synthesized multiple isomers of chloromethylpyridine and developed sulfonamide drugs.
In 1942, Hans Milwin's team reported the synthesis of 3-chloromethylpyridine, but the preparation of 2,5-disubstituted pyridine still faced challenges, mainly limited by regional selectivity control issues.
In 1958, Swiss pesticide chemist Heinz Geigy accidentally isolated CCMP from the photo chlorination reaction of 2-chloro-5-methylpyridine while studying herbicides. Through nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis, it was confirmed that its structure is 2-chloro-5-chloromethylpyridine.
The main synthesis methods in the 1960s include: free radical chlorination method: 2-chloro-5-methylpyridine reacts with chlorine gas under ultraviolet catalysis (yield of about 40%); Side chain oxidation chlorination method: First, oxidize the methyl group to carboxylic acid, then convert it to acyl chloride and reduce it (the steps are relatively complicated). Due to low production or severe pollution, these methods limit the large-scale application of CCMP.
In 1975, Tokushima Pesticide Manufacturing Co., Ltd. (Tokushima Kogyo Co., Ltd.) developed a catalytic chlorination process using phosphorus trichloride (PCl ∝). This process reacted 2-chloro-5-methylpyridine with thionyl chloride (SO ₂ Cl ₂) at 60 ° C, increasing the CCMP yield to over 75%.
In 1980 (JP55123456), this technology was patented and became the mainstream method of industrial production.
In 1984, Japanese scientist Jinzo Jingbu discovered at Bayer that CCMP could be concentrated with nitromethylamine to produce imidazoline, which was the first commercially available neonicotinoid insecticide. Its mechanism of action (selective activation of insect nACh receptors) has completely changed the market landscape of insecticides.
In the 1990s, with the emergence of new nicotine pesticides, the demand for CCMP surged
In 1991, pyridine was first listed in France;
In 1995, Jiangsu Yangnong Chemical Industry built its first 1000 ton CCMP production line;
In 1999, the global CCMP annual production capacity exceeded 20000 tons.
Frequently Asked Questions
Is 2 amino 5 Chloropyridine toxic?
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Acute oral toxicity : Assessment: The component/mixture is moderately toxic after single ingestion. Acute inhalation toxicity : Assessment: The component/mixture is moderately toxic after short term inhalation.
What is 2 chloro 5 Chloromethylpyridine CCMP?
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2-chloro-5-chloromethylpyridine (2-chloro-5-chloromethylpyridine, referred to as CCMP) is a shared key intermediate of imidacloprid, acetamiprid, nitenpyram and other neonicotinoid pesticides.
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