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70372

1,4-萘醌

Name: 1,4-萘醌
Brand: SIAL

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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属性

grade

purum

Quality Segment

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

说明

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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pictograms

GHS06,GHS05,GHS09

signalword

Danger

hcodes

H301,H314,H317,H330,H335,H410

pcodes

P260 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338

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

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1, 4-Naphthoquinone.

Yu J S.

Synlett, 25(16), 2377-2378 (2014)

Double mode of inhibition-inducing interactions of 1,4-naphthoquinone with urease: arylation versus oxidation of enzyme thiols.

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

Study of 1,4-naphthoquinone as a new useful derivatization reagent for LC analysis of aliphatic thiols in dietary supplements and pharmaceuticals.

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

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全球贸易项目编号

货号	GTIN
70372-250G	04061832822129
70372-1KG	04061835048434
70372-50G	04061835052394