Introduction：Basic information about 6-Chloronicotinic acid CAS 5326-23-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
6-Chloronicotinic acid Basic information
| Product Name: | 6-Chloronicotinic acid |
| Synonyms: | RARECHEM AL BO 0729;TIMTEC-BB SBB004004;3-Pyridinecarboxylic acid, 6-chloro-;6-chloro-3-pyridinecarboxylicaci;6-CHLORONICOTINIC ACID;6-CHLORO-3-PYRIDINECARBOXYLIC ACID;6-Chloronicotinic acid, 99% 25GR;6-Chloronicotinic acid, 99% 5GR |
| CAS: | 5326-23-8 |
| MF: | C6H4ClNO2 |
| MW: | 157.55 |
| EINECS: | 226-201-5 |
| Product Categories: | pyridine series;Picolinic acid series;Carboxylic Acids;Organic acids;Chloropyridines;Halopyridines;Nitrogen cyclic compounds;blocks;Carboxes;Pyridines;Pyridine;Carboxylic Acids;Building Blocks;C5 to C6;C6 to C7;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;C6;carboxylic acid| alkyl chloride |
| Mol File: | 5326-23-8.mol |
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6-Chloronicotinic acid Chemical Properties
| Melting point | 190 °C (dec.)(lit.) |
| Boiling point | 241.15°C (rough estimate) |
| density | 0.5 |
| refractive index | 1.5870 (estimate) |
| Fp | 192°C |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | deionized water: soluble |
| form | Crystalline Powder |
| pka | 3.24±0.10(Predicted) |
| color | Off-white to beige |
| Water Solubility | Soluble in water (2 mg/ml at 20°C), ethanol, methanol, DMSO, and slightly soluble in chloroform. |
| Decomposition | 192 ºC |
| BRN | 115993 |
| Stability: | Stable. Incompatible with strong oxidizing agents. |
| InChI | 1S/C6H4ClNO2/c7-5-2-1-4(3-8-5)6(9)10/h1-3H,(H,9,10) |
| InChIKey | UAWMVMPAYRWUFX-UHFFFAOYSA-N |
| SMILES | OC(=O)c1ccc(Cl)nc1 |
| CAS DataBase Reference | 5326-23-8(CAS DataBase Reference) |
| NIST Chemistry Reference | 6-Chloronicotinic acid(5326-23-8) |
| EPA Substance Registry System | 6-Chloronicotinic acid (5326-23-8) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36-24/25-37/39 |
| WGK Germany | 3 |
| TSCA | TSCA listed |
| HazardClass | IRRITANT |
| HS Code | 29333999 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
6-Chloronicotinic acid Usage And Synthesis
| Chemical Properties | Off-white to beige crystalline powder |
| Uses | 6-Chloronicotinic acid is used as building block for different chemical synthesis. It is an intermediate for the synthesis of N-(thiophen-2-yl) benzamide derivatives as BRAFV600E inhibitors, and novel DNA-gyrase B inhibitors. |
| Uses | 6-Chloropyridine-3-carboxylic acid (6-chloronicotinic acid/6-CNA) has been used to study its photolytic and photocatalytic degradation. 6-CNA is a degradation product of neonicotinoid insecticides imidacloprid and acetamiprid and is known to appear in different environmental matrices. The product has been used as a media component during the isolation of 6-CNA degrading bacterial strain from imidacloprid-exposed soil samples. |
| Definition | ChEBI: 6-Chloronicotinic acid is a member of pyridines and an aromatic carboxylic acid. |
| General Description | 6-Chloropyridine-3-carboxylic acid is a metabolite of the neonicotinoid pesticides, imidacloprid and acetamiprid and occurs in different environmental matrices.(3) It is widely used in agricultural crop protection, domestic insect control and environmental pest management. |
| Synthesis | In a 1000ml flask, add 450g chlorobenzene, 100g 2-chloro-5-methylpyridine, and 3g catalyst cobalt acetate under stirring, heat the system to 80℃, introduce oxygen, and control the oxygen flow rate at 0.4L/min. React under this condition for 4 hours. After the reaction, cool the system to room temperature, filter, and dry to obtain a mixture of 119g 6-chloronicotinic acid and cobalt acetate. Place those mentioned above mixed crude product in a 1000ml flask, add 600g of recrystallization solvent methanol, stir and heat to reflux; wait for the 6-chloronicotinic acid crude product to dissolve completely, keep warm for 5min, slowly cool the system to 5℃, precipitate a white product, maintain this internal temperature and continue stirring for 1 hour, filter, wash the filter cake once with a small amount of cooled methanol, and dry the obtained damp product at 80℃ for 4 hours to obtain 98.5g 6-chloronicotinic acid, purity 99.52% (HPLC), yield 79.7%.
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| Purification Methods | Purify it by recrystallisation from hot H2O and sublime it in a vacuum. [Pechmann & Welsch Chem Ber 17 2384 1884, Herz & Murty J Org Chem 26 122 1961, Beilstein 22/2 V 177.] |
6-Chloronicotinic acid Preparation Products And Raw materials
| Preparation Products | 2-chloro-5-cyanopyridine-->6-PHENOXYNICOTINIC ACID-->6-PHENOXYNICOTINOYL CHLORIDE-->6-PHENOXYNICOTINONITRILE-->TERT-BUTYL 4-(5-FORMYLPYRID-2-YL)PIPERAZINE-1-CARBOXYLATE-->6-MORPHOLINONICOTINOYL CHLORIDE-->6-Methoxynicotinic acid-->6-MORPHOLINONICOTINIC ACID-->Methyl 6-chloronicotinate-->5-(BROMOMETHYL)-2-METHOXYPYRIDINE-->5-Bromo-2-chloropyridine-->3-PYRIDINAMINE, N-METHYL-4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)--->6-(DIMETHYLAMINO)NICOTINIC ACID-->Pyridine, 5-(bromomethyl)-2-chloro- (9CI)-->(6-methoxypyridin-3-yl)methanol |
