2,6-Dichloropyridine

2,6-Dichloropyridine

Names
Preferred IUPAC name 2,6-Dichloropyridine
Identifiers
CAS Number	2402-78-0
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3561947
ChemSpider	16095
ECHA InfoCard	100.017.531
EC Number	219-282-3
PubChem CID	16989
UNII	WM26PC2SBW  Y
CompTox Dashboard (EPA)	DTXSID2051895
InChI InChI=1S/C5H3Cl2N/c6-4-2-1-3-5(7)8-4/h1-3H Key: FILKGCRCWDMBKA-UHFFFAOYSA-N
SMILES C1=CC(=NC(=C1)Cl)Cl
Properties
Chemical formula	C5H3Cl2N
Molar mass	147.99 g·mol−1
Appearance	white solid
Density	1.665 g/cm3 [1]
Melting point	86–89 °C (187–192 °F; 359–362 K)
Boiling point	211–212 °C (412–414 °F; 484–485 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H319, H335
Precautionary statements	P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2,6-Dichloropyridine is a chloropyridine with the formula C₅H₃Cl₂N. A white solid, it is one of six isomers of dichloropyridine. It serves as a precursor to the antibiotic enoxacin, ^[2] as well as the drug and anpirtoline and the antifungal liranaftate.

Synthesis

2,6-Dichoropyridine is produced by reaction of pyridine with chlorine. 2-Chloropyridine is an intermediate. ^[2]

Toxicity

The LD₅₀ is 115 mg/kg (oral, mice). ^[2]

References

1. Kumar, Parveen; Rautiainen, J. Mikko; Novotný, Jan; Ward, Jas S.; Marek, Radek; Rissanen, Kari; Puttreddy, Rakesh (2024). "The Impact of ortho -substituents on Bonding in Silver(I) and Halogen(I) Complexes of 2-Mono- and 2,6-Disubstituted Pyridines: An In-Depth Experimental and Theoretical Study". Chemistry – A European Journal. 30 (13) e202303643. doi: 10.1002/chem.202303643 . PMID   38055221.
2. Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN   978-3-527-30673-2.