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2-Chloronicotinic acid
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2-Chlornicotinsäure Strukturformel.svg 2-Chloropyridine-3-carboxylic acid 2942-59-8 correct CAS 68737 220-937-0 76258 C1=CC(=C(N=C1)Cl)C(=O)O 1S/C6H4ClNO2/c7-5-4(6(9)10)2-1-3-8-5/h1-3H,(H,9,10) IBRSSZOHCGUTHI-UHFFFAOYSA-N 93G386213F 194658 1505789
6 4 1 1 2 190–191 The Synthesis and Investigation of Pyridine and Pyrazine Analogs of Salicylates Lewis R. Fibel Paul E. Spoerri J. Am. Chem. Soc. 1948 70 11 3908–3911 10.1021/ja01191a113 18102982 2.5476258, whose "IUPAC Digitized pKa Dataset" record cites A.N.Kost, P.B.Terentev, L.A.Golovleva and A.A.Stolyarchuk, Khim.-Farm.Zh. 1, 3 (1967); CA 68, 29556a.
2-Chloronicotinic acid https://pubchem.ncbi.nlm.nih.gov/compound/76258#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov en 07 Warning 319 261 264 264+265 271 280 302+352 304+340 305+351+338 319 321 332+317 337+317 362+364 403+233 405 501
2-Chloronicotinic acid (2-CNA) is a halogenated derivative of nicotinic acid.
Synthesis
It can be synthesized by chlorination of the N-oxide of nicotinic acid or the related nicotinonitrile. Alternatively, it has been prepared by substitution of the hydroxyl group of 2-hydroxynicotinic acid or by a tandem reaction involving cyclization of various acrolein derivatives.leading references: Solubility Determination of 2-Chloronicotinic Acid and Analysis of Solvent Effect Yüfang Wu Chengmeng Wu Suyue Yan Bin Hu J. Chem. Eng. Data 2019 64 12 5578–5583 10.1021/acs.jced.9b00661
Applications
2-Chloronicotinic acid is an intermediate in the production of a variety of bioactive compounds, including boscalid10.1021/acs.oprd.9b00455 https://par.nsf.gov/servlets/purl/10167085 A Sustainable 1-Pot, 3-Step Synthesis of Boscalid Using Part per Million Level Pd Catalysis in Water 2020 Takale Balaram S. Thakore Ruchita R. Mallarapu Rushil Gallou Fabrice Lipshutz Bruce H. Organic Process Research & Development 24 101–105 212964123 and diflufenican.Changling Liu Guan Aiying Yang Jindong Efficient Approach To Discover Novel Agrochemical Candidates: Intermediate Derivatization Method Journal of Agricultural and Food Chemistry 17 December 2014 64 1 45–51 10.1021/jf5054707 25517210
Other reported uses include Propizepine,Hoffmann, Faure, Bull. Soc. Chim. Fr. 1966, 2316. Amdiglurax, Morniflumate, Niflumic acid,((Kheradmand, A.)), ((Navidpour, L.)), ((Shafaroodi, H.)), ((Saeedi-Motahar, G.)), ((Shafiee, A.)) Medicinal Chemistry Research Design and synthesis of niflumic acid-based N-acylhydrazone derivatives as novel anti-inflammatory and analgesic agents 22 5 2411–2420 May 2013 http://link.springer.com/10.1007/s00044-012-0235-3 10.1007/s00044-012-0235-3 28 August 2026 subscription nevirapine,((Grozinger, K. G.)), ((Fuchs, V.)), ((Hargrave, K. D.)), ((Mauldin, S.)), ((Vitous, J.)), ((Campbell, S.)), ((Adams, J.)) Journal of Heterocyclic Chemistry Synthesis of nevirapine and its major metabolite 32 1 259–263 January 1995 https://onlinelibrary.wiley.com/doi/10.1002/jhet.5570320144 10.1002/jhet.5570320144 28 August 2026 subscription Clonixeril, and Flunixin.((Jaouhari, R.)), ((Quinn, P.)) HETEROCYCLES Improved Process for the Preparation of 2-Methyl-3-trifluoromethylaniline: A Versatile Intermediate for Flunixin Synthesis 38 10 2243 1994 https://triggered.stanford.clockss.org/ServeContent?doi=10.3987%2Fcom-94-6822 0385-5414 10.3987/COM-94-6822 28 August 2026 free
References
Category:Aromatic acids
Category:Chloropyridines
Category:Disubstituted pyridines