2-Chloronicotinic acid

Base Information

• Chemical Name: 2-Chloronicotinic acid
• CAS No.: 2942-59-8
• Deprecated CAS: 1686072-77-4
• Molecular Formula: C6H4ClNO2
• Molecular Weight: 157.556
• Hs Code.: 2933.39
• European Community (EC) Number: 220-937-0
• NSC Number: 378
• UNII: 93G386213F
• DSSTox Substance ID: DTXSID9062726
• Nikkaji Number: J164C
• Wikipedia: 2-chloronicotinic acid
• Wikidata: Q27271592
• ChEMBL ID: CHEMBL1505789
• Mol file: 2942-59-8.mol

Synonyms:2-Chloronicotinic acid;2942-59-8;2-Chloropyridine-3-carboxylic acid;2-Chloro-3-pyridinecarboxylic acid;3-Pyridinecarboxylic acid, 2-chloro-;2-Chloro-nicotinic acid;Nicotinic acid, 2-chloro-;MFCD00006236;2-chloro nicotinic acid;3-Carboxy-2-chloropyridine;NSC 378;NSC-378;UNII-93G386213F;EINECS 220-937-0;93G386213F;EC 220-937-0;2-Chloronicotinicacid;chloronicotinic acid;2chloronicotinic acid;CNIS;2-choronicotinic acid;Niflumic acid impurity A;MLS000332085;SCHEMBL353141;NSC378;CHEMBL1505789;DTXSID9062726;2-chloropyridin-3-carboxylic acid;CHEBI:194658;HMS2619A03;2-chloropyridine 3-carboxylic acid;BCP27191;2-chloro-pyridine-3-carboxylic acid;STK394287;AKOS000119897;AB00651;AC-2515;CS-W017965;M510M47;PS-5333;SB40463;NCGC00246335-01;BP-11743;SMR000221567;SY001758;2-Chloropyridine-3-carboxylic acid, 99%;3-PYRIDINECARBOXYLIC ACID,2-CHLORO;A5493;AM20051047;BB 0218348;FT-0601274;EN300-19633;P16536;AC-907/30003060;FLUNIXIN MEGLUMINE IMPURITY A [EP IMPURITY];Q-200263;Q27271592;F2191-0179;Z104474538;Niflumic acid impurity A, European Pharmacopoeia (EP) Reference Standard;960360-14-9

Chemical Property of 2-Chloronicotinic acid

Chemical Property:

• Appearance/Colour: white to cream powder
• Vapor Pressure: 0.000168mmHg at 25°C
• Melting Point: 176-178 °C (dec.)(lit.)
• Boiling Point: 316.8 °C at 760 mmHg
• PKA: 2.07±0.25(Predicted)
• Flash Point: 145.4 °C
• PSA: 50.19000
• Density: 1.47 g/cm³
• LogP: 1.43320
• Storage Temp.: Store below +30°C.
• Solubility.: DMSO, Ethyl Acetate (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 156.9930561
• Heavy Atom Count: 10
• Complexity: 140

Purity/Quality:

99.0% ^*data from raw suppliers

2-Chloronicotinic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(N=C1)Cl)C(=O)O
• Description: 2-Chloronicotinic acid is a compound commonly encountered as an off-white to brown powder. It is an important building block for a series of agrochemicals and pharmaceuticals.
• Used in Agrochemical Industries: 2-Chloronicotinic acid finds extensive application in the agrochemical industries. It serves as a crucial intermediate for the synthesis of various herbicides and pharmaceutical drugs due to its versatility and importance as a building block. In agrochemicals, it contributes to the production of potent herbicides like diflufenican and nicosulfuron, known for their high biological activities, low toxicity, and broad spectrum.
• Used in Pharmaceutical Industries: It is utilized in the synthesis of drugs such as nevirapine, mirtazapine, pranoprofen, and 2-aminonicotinic acids, highlighting its significance in medicinal chemistry.
• Methods of production: The synthesis of 2-chloronicotinic acid involves several process routes, including methods using nicotinic acid nitrogen oxide, cyano-containing compounds, or 2-chloro-3-methyl-pyridine as raw materials, with the linear cyclization route being considered highly efficient due to its simplicity, minimal waste generation, and high yield.; Biocatalysis, particularly enzymatic reactions, offers an alternative and environmentally friendly approach for the synthesis of 2-chloronicotinic acid. Enzymes such as amidases play a significant role in catalyzing the hydrolysis of 2-chloronicotinamide to produce 2-chloronicotinic acid. Despite challenges in finding ideal catalysts, efforts in protein engineering aim to improve the catalytic properties of enzymes for efficient industrial production of 2-chloronicotinic acid through biocatalytic routes.

Technology Process of 2-Chloronicotinic acid

There total 37 articles about 2-Chloronicotinic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2 chloro-3-methylpyridine (18368-76-8) → 2-chloronicotinic acid (2942-59-8)

Guidance literature:

With ozone; acetic acid; at 20 ℃; for 5h; Reagent/catalyst; Temperature;

Reference yield: 98.0%

2-chloro-3-ethylpyridine (96440-05-0) → 2-chloronicotinic acid (2942-59-8)

Guidance literature:

With sodium acetate; ozone; acetic acid; at 20 ℃; for 5h; Temperature; Reagent/catalyst;

Reference yield: 98.0%

2-chloro-3-isopropylpyridine → 2-chloronicotinic acid (2942-59-8)

Guidance literature:

With iron(II) acetate; ozone; acetic acid; at 100 ℃; Reagent/catalyst; Temperature;

upstream raw materials:

2 chloro-3-methylpyridine

2-chloro-3-ethylpyridine

2-hydroxy-3-carboxypyridine

2-chloro-3-pyridinecarbonitrile

Downstream raw materials:

methyl 2-chloropyridine-3-carboxylate

2-(phenylthio)nicotinic acid

2-(phenylamino)nicotinic acid

2-phenoxypyridine-3-carboxylic acid

Refernces

• 1、 -. "Preparation method of 2-chloronicotinic acid". Paragraph 0029-0034. . Retrieved 2021/06/26.
• 2、 -. "Preparation method of 2-chloronicotinic acid". Paragraph 0028-0045. . Retrieved 2020/06/05.