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2-Chloro-5-(chloromethyl)pyridine

Product Name2-Chloro-5-(chloromethyl)pyridine
CAS70258-18-3
MFC6H5Cl2N
MW162.02
EINECS615-091-8
MOL File70258-18-3.mol

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)
form	Moist Crystals
pka	-0.75±0.10(Predicted)
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

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

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

https://www.alfa.com/en/catalog/L19284/
https://www.trc-canada.com/product-detail/?C364715
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

Pentanenitrile, 4-chloro-4-(chloromethyl)-5-oxo-

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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