70372

1,4-Naphthoquinone

purum, ≥96.5% (HPLC)

• Synonym(s): α-Naphthoquinone
• Empirical Formula (Hill Notation): C₁₀H₆O₂
• CAS Number: 130-15-4
• Molecular Weight: 158.15
• Beilstein: 878524
• EC Number: 204-977-6
• MDL number: MFCD00001676
• UNSPSC Code: 12352100
• PubChem Substance ID: 329762061
• NACRES: NA.22

Properties

• grade: purum
• Quality Level: 200
• Assay: ≥96.5% (HPLC)
• form: powder
• mp: 119-122 °C (lit.); 120-124 °C
• functional group: 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
• InChI key: FRASJONUBLZVQX-UHFFFAOYSA-N

Description

Application

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.

Safety Information

• Pictograms: GHS06,GHS05,GHS09
• Signal Word: Danger
• Hazard Statements: H301,H314,H317,H330,H335,H410
• Precautionary Statements: P260 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: 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
• Target Organs: Respiratory system
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): 285.8 °F
• Flash Point(C): 141 °C
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves