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Sigma-Aldrich

1,4-Naphthoquinone

purum, ≥96.5% (HPLC)

Synonym(s):

α-Naphthoquinone

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About This Item

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

grade

purum

Quality Level

200

Assay

≥96.5% (HPLC)

form

powder

mp

119-122 °C (lit.)
120-124 °C

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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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.

Signal Word

Danger

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

WGK

WGK 3

Flash Point(F)

285.8 °F

Flash Point(C)

141 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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1, 4-Naphthoquinone.
Yu J S.
Synlett, 25(16), 2377-2378 (2014)
Don Antoine Lanfranchi et al.
Organic & biomolecular chemistry, 10(31), 6375-6387 (2012-07-11)
Improving the solubility of polysubstituted 1,4-naphthoquinone derivatives was achieved by introducing nitrogen in two different positions of the naphthoquinone core, at C-5 and at C-8 of menadione through a two-step, straightforward synthesis based on the regioselective hetero-Diels-Alder reaction. The antimalarial
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
Michael G Berg et al.
Molecular and cellular biology, 32(7), 1271-1283 (2012-01-19)
Despite intensive research, there are very few reagents with which to modulate and dissect the mRNA splicing pathway. Here, we describe a novel approach to identify such tools, based on detection of the exon junction complex (EJC), a unique molecular
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)
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