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70372

1,4-萘醌

purum, ≥96.5% (HPLC)

别名:

α-萘醌

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关于此项目

经验公式（希尔记法）:
C10H6O2
化学文摘社编号:
130-15-4
分子量:
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
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grade

purum

Quality Level

200

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:
  • 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

存储类别

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

历史批次信息供参考:

分析证书(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)
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
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全球贸易项目编号

货号GTIN
70372-250G04061832822129
70372-1KG04061835048434
70372-50G04061835052394