5-Nitrobenzol-1,2-dicarbonitril
4-NITROPHTHALONITRILE · 4NPN · 4-NITROPHTALONITRILE · 4-Nitrophthalodinitrile · 4-nitro phthalic nitrile · ROXA-012 · RSYY（Avanafil)-57 · TIMTEC-BB SBB008410
Identifikatoren & physikalische Daten
| CAS No. | 31643-49-9 |
|---|---|
| Summenformel | C8H3N3O2 |
| Durchschnittliche Molmasse | 173,13 g/mol |
| Monoisotopische Masse | 173,02252634 g/mol |
| SMILES | N#Cc1ccc([N+](=O)[O-])cc1C#N |
| InChIKey | NTZMSBAAHBICLE-UHFFFAOYSA-N |
| PubChem CID | 97443 |
| EC No. | 250-748-9 |
| DTXSID | DTXSID4067642 |
| Lokaler Name | 5-Nitrobenzol-1,2-dicarbonitril |
Chemische & physikalische Eigenschaften
| XLogP | 1,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 93,4 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 302 |
| Schmelzpunkt | 142-144 °C(lit.) |
| Siedepunkt | 303.75°C (rough estimate) |
| Dichte | 1.4553 (rough estimate) |
| Brechungsindex | 1.6500 (estimate) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | Crystalline Powder, Crystals and/or Chunks |
| Farbe | Light yellow, light greenish or light gray to beige |
| Löslichkeit | Sparingly soluble in water.(0.26 g/L) (25°C), |
| BRN | 1877554 |
| Hauptanwendungen | diagnostic assay manufacturinghematologyhistology |
| InChI | InChI=1S/C8H3N3O2/c9-4-6-1-2-8(11(12)13)3-7(6)5-10/h1-3H |
| InChIKey | NTZMSBAAHBICLE-UHFFFAOYSA-N |
| SMILES | C1(C#N)=CC=C([N+]([O-])=O)C=C1C#N |
| CAS Datenbank | 31643-49-9(CAS DataBase Reference) |
| EPA chemische Informationen | 1,2-Benzenedicarbonitrile, 4-nitro- (31643-49-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 48 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: No longer Valid Update: 29-06-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/6278 |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29269090 |
| RTECS-Nr. | TI8576000 |
| R-Sätze (R) | 22-36/37/38-20/21/22 |
| Toxizität | mouse,LD50,oral,500mg/kg (500mg/kg),SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTIONBEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION,Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 52(9), Pg. 92, 1987. |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Verwenden
4-Nitrophthalonitrile is a useful chemical in organic synthesis. Dyes and metabolites.
Herstellung & Synthese
synthetische
Synthesis of 4-Nitrophthalonitrile: SOCl2 (83.5 mL. 1.144 mol) was added dropwise under nitrogen purge to dry DMF (200 mL) which had been cooled to 0-5 °C. The solution was allowed to stir for 15 min at 0-5 °C. The 4-nitrophthalamide (60.1 g, 0.286 mol) was then added and the solution was allowed to slowly warm to room temperature and react for 18 h under nitrogen purge. The solution was then slowly added to ice water to crystallize and precipitate the product. The 4-nitrophthalonitrile was collected using vacuum filtration, washed with ice cold water, and allowed to air dry overnight; yield: 45.2 g (92%); m.p.: 141 °C (det. by DSC) 1 H NMR((CD3)2SO): 8.41 (dd, 1H), 8.67 (dd, 1H), 9.03 (dd, 1H) FTIR: 3091 (m, aromatic C-H stretch), 2242 (d, CN stretch), 1534 (s, asymmetric N=O stretch), 1349 (s, symmetric N=O stretch), 853 (s, C-N stretch)