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 Level
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)
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 70372-250G | 04061832822129 |
| 70372-1KG | 04061835048434 |
| 70372-50G | 04061835052394 |