70372

1,4-Naphthochinon

purum, ≥96.5% (HPLC)

• Synonym(e): α-Naphthochinon
• Empirische Formel (Hill-System): C₁₀H₆O₂
• CAS-Nummer: 130-15-4
• Molekulargewicht: 158.15
• Beilstein: 878524
• EG-Nummer: 204-977-6
• MDL-Nummer: MFCD00001676
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 329762061
• NACRES: NA.22

Eigenschaften

• Qualität: purum
• Qualitätsniveau: 200
• Assay: ≥96.5% (HPLC)
• Form: powder
• mp (Schmelzpunkt): 119-122 °C (lit.); 120-124 °C
• Funktionelle Gruppe: ketone
• SMILES String: O=C1C=CC(=O)c2ccccc12
• InChI: 1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H
• InChIKey: FRASJONUBLZVQX-UHFFFAOYSA-N

Beschreibung

Anwendung

1,4-Naphthoquinone is the key structural moiety of many anticancer and antifungal agents.
It can be used to synthesize:

• 3,3-Disubstituted oxindoles via asymmetric Michael addition to oxindole.
• Bioactive isoindolines via asymmetric 1,3-dipolar cycloaddition to azomethine ylides generated in situ from aldehydes and diethyl aminomalonate.
• α,α-Difluoro-β-hydroxy ketone via ‘on water′ catalyst-free Mukaiyama-aldol reaction with difluoroenoxysilane.
• 2-Hydroxy-3-anilino-1,4-naphthoquinone, which shows potent in vivo antimalarial activity.

Additional appilcation include:

• As an arylation reagent for the α-arylation of aldehydes.
• As a starting material in the multi-step synthesis of benz[f]indole-4,9-diones.

Sicherheitshinweise

• Piktogramme: GHS06,GHS05,GHS09
• Signalwort: Danger
• H-Sätze: H301,H314,H317,H330,H335,H410
• P-Sätze: P260 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Gefahreneinstufungen: Acute Tox. 1 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Corr. 1C - Skin Sens. 1 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flammpunkt (°F): 285.8 °F
• Flammpunkt (°C): 141 °C
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges