1,2-Benzoldicarbonitril
1,2-DICYANOBENZENE · 1,2-BENZENEDICARBONITRILE · Phthalodinitril · PHTHALODINITRILE · O-PHTHALONITRILE · O-PHTHALODINITRILE · o-PDN · C8H4N2
Identifikatoren & physikalische Daten
| CAS No. | 91-15-6 |
|---|---|
| Summenformel | C8H4N2 |
| Durchschnittliche Molmasse | 128,13 g/mol |
| Monoisotopische Masse | 128,03744813 g/mol |
| SMILES | N#Cc1ccccc1C#N |
| InChIKey | XQZYPMVTSDWCCE-UHFFFAOYSA-N |
| PubChem CID | 7042 |
| ChEMBL | CHEMBL3185350 |
| ChEBI | CHEBI:232056 |
| EC No. | 202-044-8 |
| DTXSID | DTXSID8029604 |
| Lokaler Name | 1,2-Benzoldicarbonitril |
Chemische & physikalische Eigenschaften
| XLogP | 1 |
|---|---|
| Polarare Oberfläche (TPSA) | 47,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 178 |
| Stoffklassen | Nitrogen Compounds -> Nitriles |
| SpringerMaterials Properties | Schoenflies notation |
| LogP (Verteilungskoeffizient) | log Kow = 0.990.58 |
| Geruch | Slightly aromatic |
| Dichte | 1.238 g/cu cm1.24 g/cm³ |
| Color/Form | NEEDLES FROM WATER OR PETROLEUM ETHERBuff-colored crystalsFaint grayish yellow |
| Löslichkeit | Soluble in alcohol and etherSoluble in acetone and benzene.In water, 395 mg/l @ 25 °C.Solubility in water, g/100ml at 25 °C: 0.06benzene: 50 mg/mL, clear0.56 g/L (25 ºC) |
| Flammpunkt | 162 °C162°C |
| Siedepunkt | 304.5 °C227.54°C (rough estimate) |
| Decomposition | When heated to decomposition it emits toxic fumes of CN- and NOx /cyanides and nitrogen oxides/. |
| Schmelzpunkt | 138 °C141 °C137-139 °C (lit.) |
| Dampfdruck | 0.00569 [mmHg]0.05 millibar @ 20 °C (3.75X10-2 mm Hg)Vapor pressure, Pa at 20 °C: 4<1 Pa (25 °C) |
| Brechungsindex | 1.6231 (estimate) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Crystals or Crystalline Powder |
| Farbe | White to beige |
| pH | 7 (H2O) |
| BRN | 775028 |
| Henry-Konstante | 2.0×101 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong bases, strong acids, strong oxidizing agents, strong reducing agents. |
| InChI | 1S/C8H4N2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H |
| InChIKey | XQZYPMVTSDWCCE-UHFFFAOYSA-N |
| SMILES | N#Cc1ccccc1C#N |
| CAS Datenbank | 91-15-6(CAS DataBase Reference) |
| NIST chemische Informationen | Phthalonitrile(91-15-6) |
| EPA chemische Informationen | 1,2-Benzenedicarbonitrile (91-15-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH300 (28.4%): Fatal if swallowed [Danger Acute toxicity, oral]P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 162 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H301: Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Status: Active Update: 31-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/1983Phthalonitrile: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Gefahrenübersicht | Inhalation of high concentrations may cause CNS effects[ICSC] Emergency treatment: Benzyl cyanide[HSDB] Lethal doses cause tremor and convulsions in rats[RTECS] TLV Basis = convulsions and decreased body weightUnlike the aliphatic nitriles, aromatic nitriles such as m-phthalodinitrile do not liberate cyanide in the body. [ACGIH] An acute neurotoxinNot irritating to skin or eyes[Reference #1] See m-Phthalodinitrile. See NITRILES. |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: III |
| Chemical Dangers | Decomposes on heating. This produces toxic fumes including cyanide. On combustion, forms nitrogen oxides. Reacts with strong oxidants. |
| Packaging and Labelling | Do not transport with food and feedstuffs. |
| Toxic Combustion Products | When heated to decomposition it emits toxic fumes of hydrogen cyanide and NOx /cyanides and nitrogen oxides/. |
| Hazard Classes and Categories | Acute Tox. 2 (28.4%)Acute toxicity (Oral) - Category 3 |
Anwendungen & Verwendung
Verwenden
Phthalonitrile is used as an intermediate for chemical synthesis in the production of building blocks for colorants and coatings, life science and agricultural chemicals. It is also used as a precursor to phthalocyanine pigments (which are precursors to the blue dye in jeans), fluorescent brighteners, and photographic sensitizers.
Herstellung & Synthese
synthetische
Phthalonitrile can be produced from phthalic acid, phthalic anhydride, phthalamide, or phthalimide by reaction with ammonia and elimination of water at 300–500°C in the gas phase in the presence of a catalyst. In a single-stage continuous process, o-xylene is converted to phthalonitrile by reaction with ammonia and oxygen in the gas phase in a fluidized-bed reactor. Generally, metal oxide mixtures containing vanadium, antimony, chromium, and molybdenum, with further active components such as iron, tungsten, and alkali-metal oxides, on an alumina or silica support are used as catalysts.