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2-Chloropyridine

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2-Chloropyridine
Names
Preferred IUPAC name 2-Chloropyridine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 105788
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.316 Edit this at Wikidata
EC Number
  • 203-646-3
Gmelin Reference 130818
PubChem CID
RTECS number
  • US5950000
UNII
UN number 2822
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H4ClN/c6-5-3-1-2-4-7-5/h1-4HKey: OKDGRDCXVWSXDC-UHFFFAOYSA-N
  • InChI=1/C5H4ClN/c6-5-3-1-2-4-7-5/h1-4HKey: OKDGRDCXVWSXDC-UHFFFAOYAI
SMILES
  • Clc1ncccc1
Properties
Chemical formula C5H4ClN
Molar mass 113.54 g/mol
Appearance colorless liquid
Density 1.2 g/mL
Melting point −46 °C (−51 °F; 227 K)
Boiling point 166 °C (331 °F; 439 K)
Solubility in water 27 g/L
Acidity (pKa) 0.49
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H301, H310, H315, H319, H330, H400
Precautionary statements P260, P261, P262, P264, P270, P271, P273, P280, P284, P301+P310, P301+P312, P302+P350, P302+P352, P304+P340, P305+P351+P338, P310, P311, P312, P314, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, P501
Safety data sheet (SDS) MSDS
Related compounds
Related compounds 3-Chloropyridine
3-Bromopyridine
2-Chloromethylpyridine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

2-Chloropyridine is an aryl chloride with the formula C5H4ClN. It is a colorless liquid that is mainly used to generate fungicides and insecticides in industry. It also serves to generate antihistamines and antiarrythymics for pharmaceutical purposes. It is one of three isomers of chloropyridine.

Preparation

2-Chloropyridine is produced by direct reaction of pyridine with chlorine. The initially formed 2-chloropyridine reacts further to give 2,6-dichloropyridine.

Alternatively, 2-chloropyridines can be conveniently synthesized in high yields from pyridine-N-oxides.

2-Chloropyridine was originally prepared by the chlorination of 2-hydroxypyridine with phosphoryl chloride.

Main reactions and applications

2-Chloropyridine reacts with nucleophiles to generate pyridine derivatives substituted at the second and fourth carbons on the heterocycle. Therefore, many reactions using 2-chloropyridine generate mixtures of products which require further workup to isolate the desired isomer.

Some commercial products include pyrithione, pyripropoxyfen, chlorphenamine, and disopyramide. In these conversions, chloride is displaced. Pyrithione, the conjugate base of 2-mercaptopyridine-N-oxide, is a fungicide found in some shampoos. Oxidation 2-chloropyridine gives 2-chloropyridine-N-oxide. The antihistamine pheniramine may be generated via the reaction of phenylacetonitrile with 2-chloropyridine in the presence of a base.

Environmental properties

Although pyridine is an excellent source of carbon, nitrogen, and energy for certain microorganisms, introduction of a halogen moiety significantly retards degradation of the pyridine ring. With the exception of 4-chloropyridine, each of the mono- and di-substituted chloropyridines were found to be relatively resistant to microbiological degradation in soil or liquid media. Estimated time for complete degradation was > 30 days. 2-Chloropyridine exhibits extensive volatilization losses from water, less so when present in soil.

Toxicity

The LD50 is 64 mg/kg (dermal, rabbit).

References

  1. Linnell, R. H., J. Org. Chem., 1960, 25, 290.
  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 978-3527306732.
  3. Narendar, P.; Gangadasu, B.; Ramesh, Ch.; China Raju, B.; Jayathirtha Rao, V. (2004). "Facile and Selective Synthesis of Chloromethylpyridines and Chloropyridines Using Diphosgene/Triphosgene". Synthetic Communications. 34 (6): 1097–1103. doi:10.1081/SCC-120028642. S2CID 95706122.
  4. Pechmann, H. V.; Baltzer, O. (1891). "Ueber das α-Pyridon (α-Oxypyridin)". Berichte der Deutschen Chemischen Gesellschaft. 24 (2): 3144–3153. doi:10.1002/cber.189102402155.
  5. Cheng, Hefeng; She, Ji. 14. Improved preparation of 2-mercaptopyridine-N-oxide. Zhongguo Yiyao Gongye Zazhi. 1990, 21, (2), pp. 55-56. ISSN 1001-8255
  6. Botteghi, Carlo et al. New Synthetic Route to Pheniramines via Hydroformylation of Functionalyzed Olefins. 1994, 59, pp. 7125-7127. doi:10.1021/jo00102a044
  7. Sims, G. K. and L.E. Sommers. 1986. Biodegradation of pyridine derivatives in soil suspensions. Environmental Toxicology and Chemistry. 5:503-509.
  8. Sims, G. K. and L.E. Sommers. 1985. Degradation of pyridine derivatives in soil. Journal of Environmental Quality. 14:580-584.
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