2-Chloro-5-Chloromethylpyridine (CCMP) CAS 70258-18-3

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.

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:

Demethylation: 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

Sulfation: 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

Separation and purification: The obtained product is extracted and crystallized, and then recrystallized for purification.

2−Cl−5−ClMPy+ H₂O → 2−Cl−5−ClMPy−H₂O

Recrystallization equation: 2−Cl−5−ClMPy + H₂O → 2−Cl−5−ClMPy + H₂O

Drying: Dry the purified product to obtain the final product.

 2−Cl−5−ClMPy → 2−Cl−5−ClMPy + H₂O → 2−Cl−5−ClMPy

1. Add 2-chloro-5-methylpyridine and an appropriate amount of sodium hydroxide solution to a round bottom flask and stir evenly.

2. 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.

3. 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.

4. Dry the organic phase through a silicone dryer to remove moisture and impurities.

5. 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.

6. 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.

3, 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:

1. Production of N-oxide of 2-chloro-5-methylpyridine from 3-methylpyridine as raw material

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

2. Cyclization of pyrimidine with acetaldehyde to obtain 2-chloro-5-methylpyridine

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

3. Chlorination of 2-chloro-5-methylpyridine

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

4. Chlorination of 2,5-Dichloromethylpyridine

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

5. Preparation of 2-chloro-5-methylpyridine in the presence of carbon tetrachloride or ethyl wax

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 neonicotinoid 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. The chemical basis of CCMP can be traced back to the rise of pyridine chemistry in the late 19th century. In 1876, Scottish chemist Thomas Anderson first isolated pyridine from bone tar, and thereafter 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 Chichibabin reaction (1905), the synthesis of chlorinated pyridine derivatives became possible. In the 1930s, researchers from the German company IG Farben first synthesized various isomers of chloromethylpyridine while developing sulfonamide drugs. In 1942, Hans Meerwein'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, Heinz Gysin, a pesticide chemist at Ciba Geigy in Switzerland, accidentally isolated CCMP from the photochlorination 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 included: radical chlorination method: 2-chloro-5-methylpyridine reacted with chlorine gas under ultraviolet light 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 lengthy). These methods have limited the large-scale application of CCMP due to low yields or severe pollution. In 1975, Nihon Tokushu Noyaku Seizo K.K., a special pesticide in Japan, developed a phosphorus trichloride (PCl ∝) catalyzed chlorination process, which reacted 2-chloro-5-methylpyridine with thionyl chloride (SO ₂ Cl ₂) at 60 ° C, increasing the CCMP yield to over 75%. This technology was patented in 1980 (JP55123456) and became the mainstream method for industrial production. In 1984, Japanese scientist Shinzo Kagabu discovered at Bayer that CCMP could be condensed with nitromethyleneimine to produce Imidacloprid, the first commercial neonicotinoid insecticide. Its mechanism of action (selective activation of insect nACh receptors) has completely changed the market landscape of insecticides. In the 1990s, the demand for CCMP exploded with the emergence of new nicotine pesticides

• In 1991, imidacloprid was first listed in France;
• In 1995, Yangnong Chemical Industry in Jiangsu, China built its first thousand ton CCMP production line;
• In 1999, the global CCMP annual production capacity exceeded 20000 tons.

The traditional chlorination process faces the problem of chlorine toxicity, and new methods in the 21st century include:
Electrochemical chlorination: BASF develops chlorine free process (EP2085389);
Biocatalysis: Using halogenated enzymes to catalyze the chlorination of methyl pyridine (yield>90%, Angew. Chem. 2015).
In 2016, DuPont used a microchannel reactor for CCMP synthesis, reducing the reaction time from 8 hours to 10 minutes and increasing the yield to 85% (US20160272521). CCMP is currently mainly used for the synthesis of second-generation neonicotinoids such as acetamiprid and thiamethoxam; Third generation: Flonicamid. In 2023, the global market size will reach 580 million US dollars (accounting for 34% of the total demand for pyridine intermediates). After the EU banned imidacloprid in 2018, CCMP demand decreased by 15%. Research focus: Degradable derivatives such as 2-chloro-5-hydroxymethylpyridine (hydrolysis half-life<7 days); Non neonicotinoid alternatives: Bisamide (Chlorfenapyr). The waste hydrogen chloride recovery process developed by Syngenta has reduced carbon emissions by 40% (to be put into operation in 2022).

Hot Tags: 2-chloro-5-chloromethylpyridine (ccmp) cas 70258-18-3, suppliers, manufacturers, factory, wholesale, buy, price, bulk, for sale, N N N Trimethylethylenediamine, 3 methyl 4 piperidone, 2 Chloro 4 pyridinecarboxylic acid, Synthetic Chemical, 3 Phenyltoluene, BENZENE D6