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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