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:
Molecular Weight:
158.15
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
204-977-6
Beilstein/REAXYS Number:
878524
MDL number:
Assay:
≥96.5% (HPLC)
Form:
powder
grade
purum
Quality Segment
assay
≥96.5% (HPLC)
form
powder
mp
120-124 °C, 119-122 °C (lit.)
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
Application
1,4-Naphthoquinone is the key structural moiety of many anticancer and antifungal agents.
It can be used to synthesize:
Additional appilcation include:
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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1, 4-Naphthoquinone.
Yu J S.
Synlett, 25(16), 2377-2378 (2014)
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 70372-250G | 04061832822129 |
| 70372-1KG | 04061835048434 |
| 70372-50G | 04061835052394 |