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Merck
모든 사진(1)

주요 문서

70372

Sigma-Aldrich

1,4-Naphthoquinone

purum, ≥96.5% (HPLC)

동의어(들):

α-Naphthoquinone

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About This Item

실험식(Hill 표기법):
C10H6O2
CAS Number:
Molecular Weight:
158.15
Beilstein:
878524
EC Number:
MDL number:
UNSPSC 코드:
12352100
PubChem Substance ID:
NACRES:
NA.22

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grade

purum

Quality Level

분석

≥96.5% (HPLC)

양식

powder

mp

119-122 °C (lit.)
120-124 °C

작용기

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

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애플리케이션

1,4-Naphthoquinone is the key structural moiety of many anticancer and antifungal agents.[1]
It can be used to synthesize:[2]
  • 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:[2]
  • 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.

픽토그램

Skull and crossbonesCorrosionEnvironment

신호어

Danger

유해 및 위험 성명서

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

표적 기관

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

개인 보호 장비

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


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시험 성적서(COA)

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문서 라이브러리 방문

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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