Grundinformationen
- Standard-SMILES
O=C1OC(=O)c2cc3ccccc3cc21- InChIKey
IZJDCINIYIMFGX-UHFFFAOYSA-N- Summenformel
- C12H6O3
- Durchschnittliche Molmasse
- 198,17 g/mol
- Monoisotopische Masse
- 198,03169405
Namen und Bezeichner
- Bevorzugter Name
- Naphtho(2,3-c)furan-1,3-dione
- IUPAC
- benzo[f][2]benzofuran-1,3-dione
- Lokaler Name
- Naphtho[2,3-c]furan-1,3-dion
- Englischer Name
- 2,3-Naphthalenedicarboxylic Anhydride
- Summenformel
- C12H6O3
- Molmasse
- 198.17
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
716-39-2- PubChem CID
- 69743
- DTXSID
DTXSID9061049- UNII
- AYA8A7JT6P
- EC Number
- 211-936-6
- Nikkaji
- J193.086I
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,5
- Polarare Oberfläche (TPSA)
- 43,4 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 15
- Formalladung
- 0
- Komplexität
- 280
Physikochemische Eigenschaften
- Schmelzpunkt
- 246 °C · 246 °C
- Siedepunkt
- 275 · 275-280 °C(Press: 100 Torr)
- Dichte
- 1.449 · 1.449±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 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
- 2 · Naphtho[2,3-c]furan-1,3-dione (716-39-2)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H315 (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.
Gefahrenhinweise
Sicherheitsdaten
- tsca
- TSCA listed
- hs_code
- 2917.39.7000
- safety_code
- 22-24/25
Chemie und Industrie
Verwendung und Herstellung
Anwendungen
BeschreibungA 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.
Verwenden2,3-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.
Darstellung
synthetischeAdd 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%.
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