2-Chloropyridine is an organohalide 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.[2]
2-Chloropyridine is produced by direct reaction of pyridine with chlorine. The initially formed 2-chloropyridine reacts further to give 2,6-dichloropyridine.[2]
Alternatively, 2-chloropyridines can be conveniently synthesized in high yields from pyridine-N-oxides.[3]
2-Chloropyridine was originally prepared by the chlorination of 2-hydroxypyridine with phosphoryl chloride.[4]
Main reactions and applicationsedit
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.[2]
Some commercial products include pyrithione, pyripropoxyfen, chlorphenamine, and disopyramide. In these conversions, chloride is displaced.[2] Pyrithione, the conjugate base of 2-mercaptopyridine-N-oxide, is a fungicide found in some shampoos. Oxidation 2-chloropyridine gives 2-chloropyridine-N-oxide.[5] The antihistamine pheniramine may be generated via the reaction of phenylacetonitrile with 2-chloropyridine in the presence of a base.[6]
Environmental propertiesedit
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.[7] Estimated time for complete degradation was > 30 days. 2-Chloropyridine exhibits extensive volatilization losses from water, less so when present in soil.[8]
^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.
^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.
^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
^Botteghi, Carlo et al. New Synthetic Route to Pheniramines via Hydroformylation of Functionalyzed Olefins. 1994, 59, pp. 7125-7127. doi:10.1021/jo00102a044
^Sims, G. K. and L.E. Sommers. 1986. Biodegradation of pyridine derivatives in soil suspensions. Environmental Toxicology and Chemistry. 5:503-509.
^Sims, G. K. and L.E. Sommers. 1985. Degradation of pyridine derivatives in soil. Journal of Environmental Quality. 14:580-584.
November 28, 2023
chloropyridine, organohalide, with, formula, c5h4cln, colorless, liquid, that, mainly, used, generate, fungicides, insecticides, industry, also, serves, generate, antihistamines, antiarrythymics, pharmaceutical, purposes, namespreferred, iupac, name, identifie. 2 Chloropyridine is an organohalide 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 2 2 Chloropyridine NamesPreferred IUPAC name 2 ChloropyridineIdentifiersCAS Number 109 09 1 Y3D model JSmol Interactive imageBeilstein Reference 105788ChEBI CHEBI 39174 YChEMBL ChEMBL509579 YChemSpider 7689 YECHA InfoCard 100 003 316EC Number 203 646 3Gmelin Reference 130818PubChem CID 7977RTECS number US5950000UNII 8HMD45AYEJ YUN number 2822CompTox Dashboard EPA DTXSID8024810InChI InChI 1S C5H4ClN c6 5 3 1 2 4 7 5 h1 4H YKey OKDGRDCXVWSXDC UHFFFAOYSA N YInChI 1 C5H4ClN c6 5 3 1 2 4 7 5 h1 4HKey OKDGRDCXVWSXDC UHFFFAOYAISMILES Clc1ncccc1PropertiesChemical formula C5H4ClNMolar mass 113 54 g molAppearance colorless liquidDensity 1 2 g mLMelting point 46 C 51 F 227 K Boiling point 166 C 331 F 439 K Solubility in water 27 g LAcidity pKa 0 49 1 HazardsGHS labelling PictogramsSignal word DangerHazard statements H301 H310 H315 H319 H330 H400Precautionary 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 P501Safety data sheet SDS MSDSRelated compoundsRelated compounds 2 ChloromethylpyridineExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Preparation 2 Main reactions and applications 3 Environmental properties 4 Toxicity 5 ReferencesPreparation edit nbsp 2 Chloropyridine is produced by direct reaction of pyridine with chlorine The initially formed 2 chloropyridine reacts further to give 2 6 dichloropyridine 2 Alternatively 2 chloropyridines can be conveniently synthesized in high yields from pyridine N oxides 3 2 Chloropyridine was originally prepared by the chlorination of 2 hydroxypyridine with phosphoryl chloride 4 Main reactions and applications edit2 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 2 Some commercial products include pyrithione pyripropoxyfen chlorphenamine and disopyramide In these conversions chloride is displaced 2 Pyrithione the conjugate base of 2 mercaptopyridine N oxide is a fungicide found in some shampoos Oxidation 2 chloropyridine gives 2 chloropyridine N oxide 5 The antihistamine pheniramine may be generated via the reaction of phenylacetonitrile with 2 chloropyridine in the presence of a base 6 Environmental properties editAlthough 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 7 Estimated time for complete degradation was gt 30 days 2 Chloropyridine exhibits extensive volatilization losses from water less so when present in soil 8 Toxicity editThe LD50 is 64 mg kg dermal rabbit 2 References edit Linnell R H J Org Chem 1960 25 290 a b c d e 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 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 Pechmann H V Baltzer O 1891 Ueber das a Pyridon a Oxypyridin Berichte der Deutschen Chemischen Gesellschaft 24 2 3144 3153 doi 10 1002 cber 189102402155 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 Botteghi Carlo et al New Synthetic Route to Pheniramines via Hydroformylation of Functionalyzed Olefins 1994 59 pp 7125 7127 doi 10 1021 jo00102a044 Sims G K and L E Sommers 1986 Biodegradation of pyridine derivatives in soil suspensions Environmental Toxicology and Chemistry 5 503 509 Sims G K and L E Sommers 1985 Degradation of pyridine derivatives in soil Journal of Environmental Quality 14 580 584 Retrieved from https en wikipedia org w index php title 2 Chloropyridine amp oldid 1173881573, wikipedia, wiki, book, books, library,
