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Merck

70372

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
329762061
EC Number:
204-977-6
Beilstein/REAXYS Number:
878524
MDL number:
MFCD00001676
Assay:
≥96.5% (HPLC)
Form:
powder

Key Documents

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InChI key

FRASJONUBLZVQX-UHFFFAOYSA-N

InChI

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

SMILES string

O=C1C=CC(=O)c2ccccc12

grade

purum

assay

≥96.5% (HPLC)

form

powder

Quality Level

200

mp

120-124 °C

functional group

ketone

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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.

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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

Storage Class

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

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN9950
BCCN5958
BCCK3783
BCCD6229
BCCB2228

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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
Yu Shang et al.
Environmental science & technology, 46(5), 2935-2942 (2012-02-01)
Airborne quinones contribute to adverse health effects of ambient particles probably because of their ability to generate hydroxyl radicals (·OH) via redox cycling, but the mechanisms remain unclear. We examined the chemical mechanisms through which 1,4-naphthoquinone (1,4-NQ) induced ·OH, and
Daniela M Santos et al.
Molecular neurobiology, 47(1), 313-324 (2012-10-12)
Naphthoquinones are bioactive compounds widespread in nature that impact on several cellular pathways, including cell proliferation and survival, by acting as prooxidants and electrophiles. We have previously described the role of the synthetic isoxazole condensed 1,4-naphthoquinone derivative 1a in preventing
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