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4-Nitrophthalsureanhydrid
4-nitro pthalic anhydride · 4-nitro-anhydride · TIMTEC-BB SBB008431 · Apremilast Impurity 89 · p-NitroPhthalicAnhydride · 4-nitro-phthalicanhydrid · 4-NITROPHTHALIC ANHYDRIDE · 5-Nitrophthalic anhydride
Identifikatoren & physikalische Daten
| CAS No. | 5466-84-2 |
|---|---|
| Summenformel | C8H3NO5 |
| Durchschnittliche Molmasse | 193,11 g/mol |
| Monoisotopische Masse | 193,0011222 g/mol |
| SMILES | O=C1OC(=O)c2cc([N+](=O)[O-])ccc21 |
| InChIKey | MMVIDXVHQANYAE-UHFFFAOYSA-N |
| PubChem CID | 230976 |
| ChEMBL | CHEMBL1373184 |
| EC No. | 226-776-2 |
| DTXSID | DTXSID6025775 |
| Lokaler Name | 4-Nitrophthalsureanhydrid |
Chemische & physikalische Eigenschaften
| XLogP | 1,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 89,2 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 307 |
| Löslichkeit | 10 to 50 mg/mL at 70 °F (NTP, 1992)Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly)Hydrolysis |
| Schmelzpunkt | 246 °F (NTP, 1992)116-120 °C(lit.) |
| Physical Description | 4-nitrophthalic anhydride is a yellow powder. (NTP, 1992) |
| Siedepunkt | 197 °C / 8mmHg |
| Dichte | 1.6392 (rough estimate) |
| Brechungsindex | 1.4700 (estimate) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Aggregatzustand | Solid |
| Farbe | Pale Beige |
| BRN | 179682 |
| InChI | InChI=1S/C8H3NO5/c10-7-5-2-1-4(9(12)13)3-6(5)8(11)14-7/h1-3H |
| InChIKey | MMVIDXVHQANYAE-UHFFFAOYSA-N |
| SMILES | C1(=O)C2=C(C=C([N+]([O-])=O)C=C2)C(=O)O1 |
| CAS Datenbank | 5466-84-2(CAS DataBase Reference) |
| NIST chemische Informationen | 4-Nitrophthalic anhydride(5466-84-2) |
| EPA chemische Informationen | 5-Nitrophthalic anhydride (5466-84-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | 1,3-Isobenzofurandione, 5-nitro-: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Flash point data for this chemical are not available, however it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound include coughing, sneezing, burning in respiratory system, dermatitis, and skin irritation. Symptoms of chronic exposure include bronchitis, eye irritation, inflammation of respiratory tract and bloody nasal discharge. |
| Reaktive Gruppe | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| Reactivity Alerts | Water-Reactive |
| Reactivity Profile | 4-NITROPHTHALIC ANHYDRIDE reacts exothermically with water. The reactions are usually slow, but might become violent if local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases. |
| Air and Water Reactions | Reacts with water. The organic acids produced by this reaction are significantly more soluble in water. |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Brandbekämpfung | Fires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
Anwendungen & Verwendung
Verwenden
4-Nitrophthalic anhydride is used an an intermediate for the synthesis of a benzimidazole PARP inhibitor I (succinate salt) (ABT-472).
Herstellung & Synthese
synthetische
4-Nitrophthalic anhydride is synthesized by hydrolysis of 4-nitrophthalimide and then dehydration. The 4-nitrophthalimide was added to the sodium hydroxide solution, heated and boiled for 15min. Adjust pH to 6-8 with nitric acid, and add nitric acid to boil for 5 min. Cooling, filtering, the filtrate was extracted with ether, the extract was dried and then the ether was evaporated, that is, 4-Nitrophthalic anhydride crystals were precipitated. Yield 95%.