1,8-Dinitronaphthalin
1,8-Dinitronaphthale · 1,8-Dinitrophthalene · 1,8-Dinitronapthalene · LABOTEST-BB LT00436938 · 1,8-DINITRONAPHTHALENE · 1,8-dinitro-naphthalen · Naphthalene, 1,8-dinitro- · 1,8-Dinitronaphthalene,85%
Identifikatoren & physikalische Daten
| CAS No. | 602-38-0 |
|---|---|
| Summenformel | C10H6N2O4 |
| Durchschnittliche Molmasse | 218,17 g/mol |
| Monoisotopische Masse | 218,03275667 g/mol |
| SMILES | O=[N+]([O-])c1cccc2cccc([N+](=O)[O-])c12 |
| InChIKey | AVCSMMMOCOTIHF-UHFFFAOYSA-N |
| PubChem CID | 11764 |
| ChEMBL | CHEMBL167529 |
| ChEBI | CHEBI:50642 |
| EC No. | 210-016-1 |
| DTXSID | DTXSID9025166 |
| Lokaler Name | 1,8-Dinitronaphthalin |
Chemische & physikalische Eigenschaften
| XLogP | 2,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 91,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 268 |
| Stoffklassen | Nitrogen Compounds -> Nitros, Aromatic |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | 2.52 |
| Löslichkeit | less than 1 mg/mL at 66 °F (NTP, 1992)DMSO (Slightly), Methanol (Slightly)34mg/L(15 ºC) |
| Schmelzpunkt | 340 to 342 °F (NTP, 1992)161 °C |
| Dampfdichte | 7.51 (NTP, 1992) - Heavier than airwill sink (Relative to Air) |
| Dampfdruck | 0.00000428 [mmHg] |
| Physical Description | 1,8-dinitronaphthalene appears as yellow crystals. (NTP, 1992)Yellow solid[CAMEO] Yellow crystalline powder[MSDSonline] |
| Siedepunkt | 358.84°C (rough estimate) |
| Dichte | 1.4330 (rough estimate) |
| Brechungsindex | 1.7040 (estimate) |
| Aggregatzustand | Solid |
| Farbe | Pale Yellow to Light Yellow |
| Henry-Konstante | 5.2×103 mol/(m3Pa) at 25℃, Parnis et al. (2015) |
| Stabilität | Stability Shock and heat sensitive - may react violently if heated or ground. Combustible. Incompatible with strong oxidizing agents. |
| InChI | 1S/C10H6N2O4/c13-11(14)8-5-1-3-7-4-2-6-9(10(7)8)12(15)16/h1-6H |
| InChIKey | AVCSMMMOCOTIHF-UHFFFAOYSA-N |
| SMILES | [O-][N+](=O)c1cccc2cccc([N+]([O-])=O)c12 |
| CAS Datenbank | 602-38-0(CAS DataBase Reference) |
| NIST chemische Informationen | Naphthalene, 1,8-dinitro-(602-38-0) |
| EPA chemische Informationen | 1,8-Dinitronaphthalene (602-38-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH228 (97.5%): Flammable solid [Danger Flammable solids]P210, P240, P241, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Not Classified |
|---|---|
| Regulatorische Informationen | Naphthalene, 1,8-dinitro-: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Flash point data for this chemical is not available, however it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranesskin pigmentation, headache, dizziness, cyanosis, nausea, vomiting, anemia, insomnia, fatigue, weight loss, central nervous system depression, liver damage, toxic hepatitis, and kidney damage. |
| Gefahrenübersicht | Potentially explosive[Ullmann] ExplosiveA strong oxidizing agentA skin, eye, and mucous membrane irritantSymptoms of exposure to this compound may include skin pigmentation, headache, dizziness, cyanosis, nausea, vomiting, anemia, insomnia, fatigue, weight loss, central nervous system depression, liver damage, toxic hepatitis, and kidney damage. [CAMEO] An irritantMay induce methemoglobinemia[MSDSonline] See 2-Nitronaphthalene. |
| Reaktive Gruppe | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| Reactivity Alerts | Explosive |
| Reactivity Profile | 1,8-DINITRONAPHTHALENE is sensitive to heat and shock. (NTP, 1992) |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories |
Anwendungen & Verwendung
Verwenden
1,8-Dinitronaphthalene (cas# 602-38-0) is a compound useful in organic synthesis.
Herstellung & Synthese
synthetische
Separation of dinitronaphthalene: Crude mixtures of dinitronaphthalene (5 g, from Table-3 run 8) was placed together with 50 mL acetone in a 100 mL flask, stirred and heated to reflux. The suspension was refluxing for 2 h and then cooled to 30 oC by stirred and filtered quickly. The precipitate was recrystallized by acetone and 1,5-dinitronaphthalene as light yellow crystals (1.725 g) was got. Then the filter liquor was concentrated to one-thirds of original volume, filtered, the precipitate was recrystallized by toluene and 1,8- dinitronaphthalene as light yellow crystals (1.987 g) was got. 1, 5-Dinitronaphthalene: m.p. 215-216 oC, 1H NMR (400 MHz, CDCl3): δ = 7.84 (t, 2H), 8.33 (d, 2H), 8.81 (d, 2H). 1, 8-Dinitronaphthalene: m.p. 172-173 oC, 1H NMR (400 MHz, CDCl3): δ = 7.98 (t, 2H), 8.51 (dd, 4H). Zeolite-Assisted Regioselective Synthesis of Dinitronaphthalene