Pyridin-2,6-dicarbonsure
DIPICOLINIC ACID · PYRIDINE-2,6-DICARBOXYLIC ACID · 2,6-PYRIDINEDICARBOXYLIC ACID · 2,6-DIPICOLINIC ACID · dipicolinic · 2,6-Dicarboxypyridine · 2,6-PYRIDINECARBOXYLIC ACID · Pyridine-2,6-dicarboxylate
Identifikatoren & physikalische Daten
| CAS No. | 499-83-2 |
|---|---|
| Summenformel | C7H5NO4 |
| Durchschnittliche Molmasse | 167,12 g/mol |
| Monoisotopische Masse | 167,02185764 g/mol |
| SMILES | O=C(O)c1cccc(C(=O)O)n1 |
| InChIKey | WJJMNDUMQPNECX-UHFFFAOYSA-N |
| PubChem CID | 10367 |
| ChEMBL | CHEMBL284104 |
| ChEBI | CHEBI:46837 |
| EC No. | 207-894-3 |
| DTXSID | DTXSID7022043 |
| Lokaler Name | Pyridin-2,6-dicarbonsure |
Chemische & physikalische Eigenschaften
| XLogP | 0,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 87,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 184 |
| Löslichkeit | 5 mg/mL at 25 °CH2O: 1%, clear5 g/L (20 ºC) |
| Schmelzpunkt | 252 °C248-250 °C (dec.)(lit.) |
| Dampfdruck | 0.0000061 [mmHg]<0.01 hPa (20 °C) |
| Physical Description | White crystalline powder[Alfa Aesar MSDS]Solid |
| Siedepunkt | 295.67°C (rough estimate) |
| Dichte | 1.5216 (rough estimate) |
| Brechungsindex | 1.6280 (estimate) |
| Flammpunkt | 188 °C |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 2.16(at 25℃) |
| Aggregatzustand | Crystalline Powder |
| Farbe | White |
| pH | 2.0 (5g/l, H2O, 20℃) |
| BRN | 131629 |
| Kosmetik-Inhaltsstoffe Funktionen | CHELATING |
| InChI | 1S/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12) |
| InChIKey | WJJMNDUMQPNECX-UHFFFAOYSA-N |
| SMILES | OC(=O)c1cccc(n1)C(O)=O |
| LogP (Verteilungskoeffizient) | 0.3 at 25℃ and pH1.8 |
| CAS Datenbank | 499-83-2(CAS DataBase Reference) |
| NIST chemische Informationen | 2,6-Pyridinedicarboxylic acid(499-83-2) |
| EPA chemische Informationen | 2,6-Pyridinedicarboxylic acid (499-83-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH314 (42.9%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H315 (57.1%): Causes skin irritation [Warning Skin corrosion/irritation]H318 (48.4%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H319 (52.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (99.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 273 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: 2,6-Pyridinedicarboxylic acidStatus: Active Update: 02-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/24614Dipicolinic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | A skin and strong eye irritant[Alfa Aesar MSDS] See Pyridine and Picolinic acid. |
| Hazard Classes and Categories | Skin Corr. 1B (42.9%)Skin Irrit. 2 (57.1%)Eye Dam. 1 (48.4%)Eye Irrit. 2A (52.4%)STOT SE 3 (99.6%) |
| Protective Action Criteria (PAC) | 12 [mg/m3]130 [mg/m3]790 [mg/m3] |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29333999 |
| R-Sätze (R) | 36/37/38-37/38-36 |
| Toxizität | LD50 orally in Rabbit: 10500 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36-24/25-37 |
| Gefahrenklasse | IRRITANTEye Dam. 1Skin Corr. 1BSTOT SE 3 |
| Lagerklasse | 8A - Combustible corrosive hazardous materials |
| Selbstentzündungstemperatur | 620 °C |
Anwendungen & Verwendung
Beschreibung
2,6-Pyridinedicarboxylic acid (PDCA) contains two carboxylic groups on each side of the pyridine ring. Both groups form rigid 120° angles with the pyridine. Carboxylic functionality could be complex and bind with metals under certain conditions. Numerous metalorganic frameworks, metal complexes, drugs, and CPs based on PDCA were developed for applications related to gas storage, separation, catalysis, magnetism, and sensing[1]. Shao et al. researched the solubility of PDCA in methanol, ethanol, n-propanol, isopropanol, THF, 1,4-dioxane, acetic acid, formic acid, acetonitrile, ethyl acetate, and toluene. They found that PDCA solubility was the highest in methanol but the lowest in acetonitrile.
Herstellung & Synthese
synthetische
pyridine-2,6-dicarboxylic acid was synthesized by hydrolyzing of ester prepared by coupling of diethyl 4-hydroxypyridine-2,6-dicarboxylate to bis-halohydrocarbon or bis-halide.Synthesis of Novel Derivatives of Pyridine‐2,6‐dicarboxylic Acid