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)

Flash point:

>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

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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

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(70258-18-3)Related Product Information

• 2-Chloro-5-trichloromethylpyridine
• 2-(Chloromethyl)pyridine
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• Chromium picolinate
• Pyridine
• Clopidol
• Azamethiphos
• 2,4,6-Collidine
• 4-Methylpyridine
• 2-Chloro-5-methylpyridine
• 2,6-DICHLORO-5-FLUORONICOTINOYL CHLORIDE
• 2,6-DICHLORO-3-(CHLOROMETHYL)PYRIDINE
• 2,3-Dichloro-5-(trichloromethyl)pyridine
• Difluorochloromethane
• 6-CHLORONICOTINOYL CHLORIDE
• 2,6-dichloro-3-(trichloromethyl)pyridine
• 2-CHLORO-5-(CHLOROMETHYL)PYRIDINE HYDROCHLORIDE
• 2,4-DICHLORO-5-(CHLOROMETHYL)-PYRIDINE