2-Chloropyridine

changed changed 477213072 2-chloropyridine.png 120px skin-invert 2-Chloropyridine Ball and Stick.png 130 bg-transparent 2-Chloropyridine Space Fill.png 120 bg-transparent 2-Chloropyridine 2-Chloropyridine correct chemspider 7689 1/C5H4ClN/c6-5-3-1-2-4-7-5/h1-4H correct EBI 39174 Clc1ncccc1 OKDGRDCXVWSXDC-UHFFFAOYAI correct EBI 509579 correct chemspider 1S/C5H4ClN/c6-5-3-1-2-4-7-5/h1-4H correct chemspider OKDGRDCXVWSXDC-UHFFFAOYSA-N correct CAS 109-09-1 correct FDA 8HMD45AYEJ 7977 203-646-3 US5950000 2822 105788 130818 5 4 1 1 colorless liquid 1.2 g/mL 27 g/L -46 166 0.49 (for C5H4ClNH+) Linnell Robert Notes- Dissociation Constants of 2-Substituted Pyridines The Journal of Organic Chemistry 1960 25 2 290 10.1021/jo01072a623 MSDS 05 06 07 08 09 Danger 301 310 315 319 330 400 260 261 262 264 270 271 273 280 284 301+310 301+312 302+350 302+352 304+340 305+351+338 310 311 312 314 320 321 322 330 332+313 337+313 361 362 363 391 403+233 405 501 3-Chloropyridine3-Bromopyridine2-Chloromethylpyridine 2-Chloropyridine is an organic compound with the fomula ClC5H4N. 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.Shinkichi Shimizu Nanao Watanabe Toshiaki Kataoka Takayuki Shoji Nobuyuki Abe Sinji Morishita Hisao Ichimura Pyridine and Pyridine Derivatives 2007 10.1002/14356007.a22_399 It is one of three isomers of chloropyridine. Preparation 500px| 2-Chloropyridine is produced by direct reaction of pyridine with chlorine. Alternatively, 2-chloropyridines can be conveniently synthesized in high yields from pyridine-N-oxides.10.1081/SCC-120028642 Facile and Selective Synthesis of Chloromethylpyridines and Chloropyridines Using Diphosgene/Triphosgene 2004 Narendar P. Gangadasu B. Ramesh Ch. China Raju B. Jayathirtha Rao V. Synthetic Communications 34 6 1097–1103 95706122 2-Chloropyridine was originally prepared by the chlorination of 2-hydroxypyridine with phosphoryl chloride.10.1002/cber.189102402155 Ueber das α-Pyridon (α-Oxypyridin) 1891 Pechmann H. V. Baltzer O. Berichte der Deutschen Chemischen Gesellschaft 24 2 3144–3153 https://zenodo.org/record/2361968 Main reactions and applications 2-Chloropyridine reacts further with chlorine to give 2,6-dichloropyridine. 2-Chloropyridine undergoes substitution at the C-Cl bond.Kevin W. C. Poon, Philip A. Albiniak, Gregory B. Dudley Protection of Alcohols Using 2-Benzyloxy-1-Methylpyridinium Trifluoromethanesulfonate: Methyl (R)-(-)-3-Benzyloxy-2-Methyl Propanoate Organic Syntheses 2007 84 295 10.15227/orgsyn.084.0295 freet-Butyl as a Pyrazole Protecting Group: Preparation and Use of 1-tert-Butyl-3-Methyl-1H-Pyrazole-5-Amine Organic Syntheses 2012 89 537 10.15227/orgsyn.089.0537 free Patrick M. Pollock, Kevin P. Cole 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.Cheng, Hefeng; She, Ji. 14. Improved preparation of 2-mercaptopyridine-N-oxide. Zhongguo Yiyao Gongye Zazhi. 1990, 21, (2), pp. 55-56. 1001-8255 The antihistamine pheniramine may be generated via the reaction of phenylacetonitrile with 2-chloropyridine in the presence of a base. Botteghi Carlo Chelucci Giorgio Del Ponte Gino Marchetti Mauro Paganelli Stefano New Synthetic Route to Pheniramines via Hydroformylation of Functionalyzed Olefins The Journal of Organic Chemistry 1994 59 23 7125–7127 10.1021/jo00102a044 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.Sims, G. K. and L.E. Sommers. 1986. Biodegradation of pyridine derivatives in soil suspensions. Environmental Toxicology and Chemistry. 5:503-509. Estimated time for complete degradation was > 30 days. 2-Chloropyridine exhibits extensive volatilization losses from water, less so when present in soil.Sims, G. K. and L.E. Sommers. 1985. Degradation of pyridine derivatives in soil. Journal of Environmental Quality. 14:580-584. Toxicity The is 64 mg/kg (dermal, rabbit). References Category:Chloropyridines Category:2-Pyridyl compounds