Pyridin-2,6-diyldiamin
2,6-DAP · Diaminopyridine · 6-DiaMinopyridine · 2,6-Pyridinediamine · pyridine-2,6-diyldiamine · 26BD · NSC 403346 · RODOL 26PYR
Identifikatoren & physikalische Daten
| CAS No. | 141-86-6 |
|---|---|
| Summenformel | C5H7N3 |
| Durchschnittliche Molmasse | 109,13 g/mol |
| Monoisotopische Masse | 109,06399722 g/mol |
| SMILES | Nc1cccc(N)n1 |
| InChIKey | VHNQIURBCCNWDN-UHFFFAOYSA-N |
| PubChem CID | 8861 |
| ChEMBL | CHEMBL339234 |
| EC No. | 205-507-2 |
| DTXSID | DTXSID0040127 |
| Lokaler Name | Pyridin-2,6-diyldiamin |
Chemische & physikalische Eigenschaften
| XLogP | 0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 64,9 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 66,1 |
| Stoffklassen | Nitrogen Compounds -> Pyridines |
| Kosmetika | Hair dyeing |
| Siedepunkt | 285 °C @760 [mm Hg]285 °C (lit.) |
| Physical Description | Slightly brown solid[EC: SCCS - Opinion] Light brown, yellow, or off-white powder or flakes[Alfa Aesar MSDS] |
| Ionization Efficiency | Positive3.051.9Agilent XCTElectrospray ionizationtrifluoroacetic acid (10.4nM) |
| Collision Cross Section | 119.8 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID0040127] |
| Schmelzpunkt | 117-122 °C (lit.) |
| Dichte | 1.7110 (rough estimate) |
| Brechungsindex | 1.5340 (estimate) |
| Flammpunkt | 155°C |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | 180g/l9.9 g/100 mL (20 ºC) |
| pKa (Säurekonstante) | 6.13±0.24(Predicted) |
| Aggregatzustand | Flakes or Crystalline Powder |
| Farbe | Beige to dark brown-gray |
| pH | >7 (H2O) |
| BRN | 108513 |
| Kosmetik-Inhaltsstoffe Funktionen | HAIR DYEING |
| InChI | 1S/C5H7N3/c6-4-2-1-3-5(7)8-4/h1-3H,(H4,6,7,8) |
| InChIKey | VHNQIURBCCNWDN-UHFFFAOYSA-N |
| SMILES | Nc1cccc(N)n1 |
| LogP (Verteilungskoeffizient) | 0.550 (est) |
| CAS Datenbank | 141-86-6(CAS DataBase Reference) |
| NIST chemische Informationen | 2,6-Pyridinediamine(141-86-6) |
| EPA chemische Informationen | 2,6-Pyridinediamine (141-86-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (99%): Toxic if swallowed [Danger Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 103 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 2,6-Pyridinediamine2,6-Diaminopyridine: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | One report of occupational contact dermatitis in the pharmaceutical industry[NTP] A strong sensitizer based on the mouse local lymph node assay (LLNA)Oral LD50 (rat) = 50-300 mg/kgA 90-day oral study of rats demonstrated the erythrocytes, spleen, kidney, and liver as target organs of toxicity (most changes recovering after 4-week recovery period)Developmental toxicity (decreased fetal and placental weights and incomplete thoracic vertebrae ossification) but no teratogenicity observed in oral study of rats in the presence of maternal toxicity[EC: SCCS - Opinion] An irritantToxic by ingestion[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Acute Tox. 3 (99%) |
| Protective Action Criteria (PAC) | 0.33 [mg/m3]3.6 [mg/m3]22 [mg/m3] |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| F | 9 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer |
Anwendungen & Verwendung
Beschreibung
2,6-Diaminopyridine is an important organic reagent with a wide range of uses. It can be used for fluorescence detection, 2,6-Diaminopyridine fluorescence method for the determination of certain aromatic primary amines. It can also be used to prepare 2,6-Diaminopyridine imprinted core-shell nanoparticles. A new method for the detection of diaminopyridine derivatives using molecularly imprinted electrochemical sensors has been established, which has been applied to the detection of 2,6-Diaminopyridine in hair dyes with good sensitivity and selectivity.
Verwenden
2,6-Diaminopyridine, used as a pharmaceutical intermediate and a hair dye coupler in oxidation/permanent formulations.
Herstellung & Synthese
synthetische
In a 600 mL autoclave equipped with a gas entrapment stirrer, a solution of 5 g CuI in 120 g aqueous ammonia (30% NH3 by weight) was added and mixed with 77 g ammonium acetate and 60 g of 2, 6-dichloropyridine. After purging with nitrogen, 24 g of liquid ammonia was added resulting in a pressure of about 150 psi (1.03 MPa). Subsequently, the reaction mixture was heated to 150°C for 8 h under stirring. Throughout the reaction, the pressure decreased from an initial pressure of 680 psi (4.69 MPa) to 450 psi (3.10 MPa). The reaction mixture was allowed to cool to room temperature, and the pressure was brought back to atmospheric pressure. Finally, 2,6-Diaminopyridine was obtained after purification.