2-Chloronicotinic acid

2-Chloronicotinic acid
Names
	IUPAC name 2-Chloropyridine-3-carboxylic acid
Identifiers
CAS Number	2942-59-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:194658;
ChEMBL	ChEMBL1505789;
ChemSpider	68737;
ECHA InfoCard	100.019.034
EC Number	220-937-0;
PubChem CID	76258;
UNII	93G386213F;
CompTox Dashboard (EPA)	DTXSID9062726 ;
	InChI InChI=1S/C6H4ClNO2/c7-5-4(6(9)10)2-1-3-8-5/h1-3H,(H,9,10) Key: IBRSSZOHCGUTHI-UHFFFAOYSA-N;
	SMILES C1=CC(=C(N=C1)Cl)C(=O)O;
Properties
Chemical formula	C6H4ClNO2
Molar mass	157.55 g·mol−1
Melting point	190–191 °C (374–376 °F; 463–464 K)
Acidity (pKa)	2.54
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P261, P264, P264 P265, P271, P280, P302 P352, P304 P340, P305 P351 P338, P319, P321, P332 P317, P337 P317, P362 P364, 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-Chloronicotinic acid (2-CNA) is a halogenated derivative of nicotinic acid that is used as an intermediate in the production of a variety of bioactive compounds,^[4] including boscalid^[5] and diflufenican.^[6] It can be synthesized by chlorination of the N-oxide of nicotinic acid or related nicotinyl compounds, by substitution of the hydroxyl group of 2-hydroxynicotinic acid, or by a tandem reaction involving cyclization of various acrolein derivatives.

References

^ CID 76258 from PubChem, 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.
^ Fibel, Lewis R.; Spoerri, Paul E. (1948). "The Synthesis and Investigation of Pyridine and Pyrazine Analogs of Salicylates". J. Am. Chem. Soc. 70 (11): 3908–3911. doi:10.1021/ja01191a113. PMID 18102982.
^ "2-Chloronicotinic acid". pubchem.ncbi.nlm.nih.gov.
^ Wu, Yüfang; Wu, Chengmeng; Yan, Suyue; Hu, Bin (2019). "Solubility Determination of 2-Chloronicotinic Acid and Analysis of Solvent Effect". J. Chem. Eng. Data. 64 (12): 5578–5583. doi:10.1021/acs.jced.9b00661.
^ Takale, Balaram S.; Thakore, Ruchita R.; Mallarapu, Rushil; Gallou, Fabrice; Lipshutz, Bruce H. (2020). "A Sustainable 1-Pot, 3-Step Synthesis of Boscalid Using Part per Million Level Pd Catalysis in Water". Organic Process Research & Development. 24: 101–105. doi:10.1021/acs.oprd.9b00455. S2CID 212964123.
^ Changling, Liu; Guan, Aiying; Yang, Jindong (17 December 2014). "Efficient Approach To Discover Novel Agrochemical Candidates: Intermediate Derivatization Method". Journal of Agricultural and Food Chemistry. 64 (1): 45–51. doi:10.1021/jf5054707. PMID 25517210.

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