2-Chlornicotinsaeure
2-CHLOROPYRIDINE-3-CARBOXYLIC ACID · CHLORONICOTINIC ACID · 2-CHLORO-3-PYRIDINECARBOXYLIC ACID · 2CLNA · 2-Chloronicoti · AKOS BBS-00004231 · 2 - chloro niacin · oronicotinic acid
Identifikatoren & physikalische Daten
| CAS No. | 2942-59-8 |
|---|---|
| Summenformel | C6H4ClNO2 |
| Durchschnittliche Molmasse | 157,55 g/mol |
| Monoisotopische Masse | 156,99305605 g/mol |
| SMILES | O=C(O)c1cccnc1Cl |
| InChIKey | IBRSSZOHCGUTHI-UHFFFAOYSA-N |
| PubChem CID | 76258 |
| ChEMBL | CHEMBL1505789 |
| ChEBI | CHEBI:194658 |
| EC No. | 220-937-0 |
| DTXSID | DTXSID9062726 |
| Lokaler Name | 2-Chlornicotinsaeure |
Chemische & physikalische Eigenschaften
| XLogP | 1,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 50,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 140 |
| SpringerMaterials Properties | Nuclear quadrupole resonance spectroscopy |
| Pestizide | Environmental transformation -> Pesticide transformation products (metabolite, successor) |
| Schmelzpunkt | 176-178 °C (dec.)(lit.) |
| Siedepunkt | 316.8±22.0 °C(Predicted) |
| Dichte | 1.470±0.06 g/cm3(Predicted) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | DMSO, Ethyl Acetate (Slightly) |
| pKa (Säurekonstante) | 2.07±0.25(Predicted) |
| Aggregatzustand | Powder |
| Farbe | White to cream |
| Geruch | Pungent odor |
| BRN | 119023 |
| InChI | InChI=1S/C6H4ClNO2/c7-5-4(6(9)10)2-1-3-8-5/h1-3H,(H,9,10) |
| InChIKey | IBRSSZOHCGUTHI-UHFFFAOYSA-N |
| SMILES | C1(Cl)=NC=CC=C1C(O)=O |
| LogP (Verteilungskoeffizient) | 0.988 |
| CAS Datenbank | 2942-59-8(CAS DataBase Reference) |
| EPA chemische Informationen | 2-Chloronicotinic acid (2942-59-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 8.1% (11 of 136) of reports.WarningH315 (14.7%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 136 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 13-04-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/7352 |
| Hazard Classes and Categories | Skin Irrit. 2 (14.7%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29333999 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 22-24/25-37/39-26-36 |
| Gefahrenklasse | IRRITANTEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
2-Chloronicotinic Acid is used in the preparation of 4-thiazolidinone derivatives and Schiff bases displaying antimicrobial activity.
Herstellung & Synthese
synthetische
Chloronicotinic acid was synthesized from nicotinic acid by oxidation by H2O2 and then chlorinationby POCl3 and PCl5 in a yield of 87.5%.Synthesis of 2-chloronicotinic acid: Pour chlorine gas into the mixed solution of phosphorus oxychloride and phosphorus trichloride, control the temperature at about 60°C, until the remaining chlorine gas escapes, cool and add nicotinic acid N-oxide in batches, and heat the mixed solution. The reaction was carried out at 100-105°C for 1-1.5 h, and the reaction mixture was stirred for 30 min after the reaction mixture was transparent, and phosphorus oxychloride was removed under reduced pressure. The obtained residue was cooled to room temperature, and water was added to obtain the finished product of 2-chloronicotinic acid.