2-Chloro-5-(chloromethyl)pyridine CAS 70258-18-3

Introduction：Basic information about 2-Chloro-5-(chloromethyl)pyridine CAS 70258-18-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

2-Chloro-5-(chloromethyl)pyridine Basic information

• Product Name: 2-Chloro-5-(chloromethyl)pyridine
• Synonyms: 2-CHLORO-5-CHLOROMETHYLPYRIDINE 90%;2-Chloro-5-ChloroMethylPyridine(Ccmp)98%;2-Chloro-5-Chloro Methyl Pyridine (Ccmp) 98%;Pyridine, 2-chloro-5-(chloromethyl)- (9CI);2-Chloro-5-chloromethylpyridine, tech., 90%;imidacloprid impurity;2-CHLORO-5-(CHLOROMETHYL)PYRIDINE[FOR IMIDACLOPRID];2-CHLORO-5-CHLOROMETHYLPYRIDINE 2-CHLORO-5-CHLOROMETHYLPYRIDINE
• CAS: 70258-18-3
• MF: C6H5Cl2N
• MW: 162.02
• EINECS: 615-091-8
• Product Categories: Pharmaceutical intermediates;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines;Chloropyridines;Halopyridines;Methyl Halides;Heterocycle-Pyridine series;API Intermediate;Pyridine series;Methyl Halides;HALOMETYL;Pyridine;70258-18-3
• Mol File: 70258-18-3.mol

2-Chloro-5-(chloromethyl)pyridine Chemical Properties

• Melting point: 37-42 °C(lit.)
• Boiling point: 267.08°C (rough estimate)
• density: 1.4411 (rough estimate)
• refractive index: 1.6000 (estimate)
• Fp: >230 °F
• storage temp.: Inert atmosphere,2-8°C
• solubility: DMSO (Slightly), Methanol (Slightly)
• pka: -0.75±0.10(Predicted)
• form: Moist Crystals
• color: Beige
• Water Solubility: Insoluble in water.
• BRN: 1635690
• InChI: InChI=1S/C6H5Cl2N/c7-3-5-1-2-6(8)9-4-5/h1-2,4H,3H2
• InChIKey: SKCNYHLTRZIINA-UHFFFAOYSA-N
• SMILES: C1(Cl)=NC=C(CCl)C=C1
• CAS DataBase Reference: 70258-18-3(CAS DataBase Reference)

Safety Information

• Hazard Codes: C,Xi,F
• Risk Statements: 22-34-36-10
• Safety Statements: 26-36/37/39-45-25-36-16
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• Hazard Note: Corrosive/Harmful
• HazardClass: LACHRYMATOR, CORROSIVE
• HazardClass: 8
• PackingGroup: II
• HS Code: 29333999
• Storage Class: 8A - Combustible corrosive hazardous materials
• Hazard Classifications: Acute Tox. 4 Oral Skin Corr. 1B

2-Chloro-5-(chloromethyl)pyridine Usage And Synthesis

Description

2-Chloro-5-chloromethylpyridine is used for the synthesis of various pharmaceutical compounds. It can also be used for the synthesis of new neonicotinoid compounds¹, having insecticidal activity. It is the raw material of pesticide products such as imidacloprid, acetamiprid as well as bactericide and herbicide^2,3.

Structure

2-Chloro-5-(chloromethyl)pyridine, C6H5Cl2N, is almost planar, with an r.m.s. deviation of 0.0146 Å for all atoms except for the 5-choloromethyl Cl atom. The offset Cl atom lies above this plane with a Cl—C—C angle of 111.11 (17)°. In the crystal, mol­ecules are connected via inter­molecular C—H⋯N hydrogen bonds, forming dimers. The crystals were obtained by dissolving 2-Chloro-5-(chloromethyl)pyridine (0.2 g, 1.2 mmol) in ethanol (25 ml) and evaporating the solvent slowly at room temperature for about 5 d[1].

Sources

1. https://www.alfa.com/en/catalog/L19284/
2. https://www.trc-canada.com/product-detail/?C364715
3. www.szqhbio.com/wap_news_detailen/id/1.htm

Chemical Properties

beige moist crystals

Uses

2-Chloro-5-(chloromethyl)pyridine is used for the synthesis of various pharmaceutical compounds. It can also be used for the synthesis of new neonicotinoid compounds.

Synthesis

150807-86-6

70258-18-3

General procedure for the synthesis of 2-chloro-5-chloromethylpyridine from the compound (CAS:150807-86-6): 18 g (0.1 mol) of 2-chloro-2-chloromethyl-4-cyano-butanal was dissolved in 50 ml of toluene, and 33 g (1.1 eq.) of solid phosgene was added to the toluene solution. The reaction mixture was stirred at 50°C for 5 hours. Upon completion of the reaction, the mixture was cooled to facilitate crystallization to afford the acetamiprid intermediate 2-chloro-5-chloromethylpyridine in 97% yield. Subsequently, the acetamiprid prodrug was further synthesized in 95% yield through methylation and esterification reaction steps.

References

[1] Zhi-Qiang Feng. “2-Chloro-5-(chloro-meth-yl)pyridine.” Acta crystallographica. Section E, Structure reports online 67 Pt 2 (2011): o366.

2-Chloro-5-(chloromethyl)pyridine Preparation Products And Raw materials

• Raw materials: Phosphorus pentoxide-->Nicotinic acid-->1,3-Cyclopentadiene-->2-Chloro-5-methylpyridine-->2-Chloro-5-trichloromethylpyridine-->3-(Chloromethyl)pyridine-->Pentanenitrile, 4-chloro-4-(chloromethyl)-5-oxo--->Pentanamide, 4-chloro-4-(chloromethyl)-5-oxo--->2-Chloro-5-hydroxymethylpyridine-->(6-methoxypyridin-3-yl)methanol-->5-(hydroxymethyl) pyridin-2(1H)-one-->N,N-Dibutylformamide-->Methyl 6-chloronicotinate-->6-Chloronicotinic acid-->Cyanuric chloride
• Preparation Products: Acetamiprid-->4-(6-Chloro-pyridin-3-ylMethyl)-piperazine-1-carboxylic acid tert-butyl ester, 98+% C15H22ClN3O2, MW: 311.81-->2-chloro-5-(piperidin-1-ylmethyl)pyridine-->2-chloro-5-[(methylthio)methyl]pyridine(SALTDATA: FREE)