Naphtho[2,3-c]furan-1,3-dion
naphtho[2,3-c]furan-1,3-dione · EA253 · 2,3-NAPHTHALI · 2,3-NAPHTHALIC ANHYDRIDE · benzo[f][2]benzofuran-1,3-dione · 2,3-Napthalenedicarboxycanhydride · benzo[f]isobenzofuran-1,3-quinone · 2,3-NAPHTHALENEDICARBOXYLIC ANHYDRIDE
![Molekülstruktur von Naphtho[2,3-c]furan-1,3-dion](/img/chemical/69743.png)
Identifikatoren & physikalische Daten
| CAS No. | 716-39-2 |
|---|---|
| Summenformel | C12H6O3 |
| Durchschnittliche Molmasse | 198,17 g/mol |
| Monoisotopische Masse | 198,03169405 g/mol |
| SMILES | O=C1OC(=O)c2cc3ccccc3cc21 |
| InChIKey | IZJDCINIYIMFGX-UHFFFAOYSA-N |
| PubChem CID | 69743 |
| EC No. | 211-936-6 |
| DTXSID | DTXSID9061049 |
| Lokaler Name | Naphtho[2,3-c]furan-1,3-dion |
Chemische & physikalische Eigenschaften
| XLogP | 2,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 43,4 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 280 |
| Schmelzpunkt | 246 °C |
| Siedepunkt | 275-280 °C(Press: 100 Torr) |
| Dichte | 1.449±0.06 g/cm3(Predicted) |
| Lagerbedingungen | under inert gas (nitrogen or Argon) at 2-8°C |
| Löslichkeit | Chloroform (Slightly), Ethyl Acetate (Slightly) |
| Aggregatzustand | Solid |
| Farbe | Pale Beige |
| Stabilität | Moisture Sensitive |
| InChI | InChI=1S/C12H6O3/c13-11-9-5-7-3-1-2-4-8(7)6-10(9)12(14)15-11/h1-6H |
| InChIKey | IZJDCINIYIMFGX-UHFFFAOYSA-N |
| SMILES | O1C(=O)C2=CC3C(C=C2C1=O)=CC=CC=3 |
| EPA chemische Informationen | Naphtho[2,3-c]furan-1,3-dione (716-39-2) |
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 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 2917.39.7000 |
| Sicherheitshinweise (S) | 22-24/25 |
Anwendungen & Verwendung
Beschreibung
A few years ago, the product was still synthesized from the corresponding diacid, but in recent years, it has been difficult to find the shadow of the diacid in the market, and the sales of this product have been repeatedly restricted, resulting in high prices.
Verwenden
2,3-Naphthalic anhydride is used as a reagent to synthesize analogues of Thalidomide (T338850), an inhibitor of tumour necrosis factor that was once abandoned because it caused birth defects, but is currently used as an inhibitor of angiogenesis in patients with multiple myeloma.
Herstellung & Synthese
synthetische
Add anhydrous tetrahydrofuran (its mass ratio to maleic anhydride is 1.5:1), cat-1 (0.05 mole), maleic anhydride (1 mole), and o-phthalaldehyde (1.5 mole) to the reactor. After adding triethylamine (5 moles), adjust the temperature below -40°C. Silicon tetrachloride (4 moles) was added dropwise to the reaction system and the reaction was placed at -40 °C for 4 h. The mixture was heated to reflux for 20 h. After the end of the reaction, concentrating the solution to a certain concentration with diatomaceous earth filtration. A light yellow solid, namely 2,3-Naphthalenedicarboxylic Anhydride, is obtained by precipitation, filtration, recrystallization and drying. Its yield reaches 88%.