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Sigma-Aldrich

1,4-Naphthoquinone

purum, ≥96.5% (HPLC)

Sinônimo(s):

α-Naphthoquinone

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About This Item

Fórmula empírica (Notação de Hill):
C10H6O2
Número CAS:
130-15-4
Peso molecular:
158.15
Beilstein:
878524
Número CE:
204-977-6
Número MDL:
MFCD00001676
Código UNSPSC:
12352100
ID de substância PubChem:
329762061
NACRES:
NA.22

grau

purum

Nível de qualidade

200

Ensaio

≥96.5% (HPLC)

forma

powder

pf

119-122 °C (lit.)
120-124 °C

cadeia de caracteres SMILES

O=C1C=CC(=O)c2ccccc12

InChI

1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H

chave InChI

FRASJONUBLZVQX-UHFFFAOYSA-N

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Aplicação

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.

Palavra indicadora

Danger

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

285.8 °F

Ponto de fulgor (°C)

141 °C

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Choose from one of the most recent versions:

Certificados de análise (COA)

Lot/Batch Number
BCCK3783
BCCD6229
BCCB2228
BCBZ4058
BCBV3637

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Acetato de etila anhydrous, 99.8%

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Acetato de etila

1, 4-Naphthoquinone.
Yu J S.
Synlett, 25(16), 2377-2378 (2014)
Design, synthesis and evaluation of novel 1, 4-naphthoquinone derivatives as antifungal and anticancer agents.
Tandon V K, et al.
Bioorganic & Medicinal Chemistry Letters, 14(5), 1079-1083 (2004)
Barbara Krajewska et al.
Bioorganic & medicinal chemistry, 15(12), 4144-4151 (2007-04-10)
In their inhibition-inducing interactions with enzymes, quinones primarily utilize two mechanisms, arylation and oxidation of enzyme thiol groups. In this work, we investigated the interactions of 1,4-naphthoquinone with urease in an effort to estimate the contribution of the two mechanisms
Rita Gatti et al.
Analytical and bioanalytical chemistry, 405(2-3), 817-825 (2012-07-24)
The use of 1,4-naphthoquinone as an advantageous pre-column reagent for liquid chromatography analysis of aliphatic thiol compounds is proposed. The compound reacts selectively in mild conditions (5 min at room temperature; pH 7.5) with thiol function. The resulting adducts were
Jan Bitenc et al.
Materials (Basel, Switzerland), 13(3) (2020-01-25)
Organic cathode materials are promising cathode materials for multivalent batteries. Among organic cathodes, anthraquinone (AQ) has already been applied to various metal‒organic systems. In this work, we compare electrochemical performance and redox potential of AQ with 1,4-naphthoquinone (NQ) and 1,4-benzoquinone
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