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523429

Sigma-Aldrich

2,3-Dibromo-1,4-naphthoquinone

97%

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About This Item

Fórmula empírica (notación de Hill):
C10H4Br2O2
Número de CAS:
13243-65-7
Peso molecular:
315.95
EC Number:
236-223-7
MDL number:
MFCD00019526
UNSPSC Code:
12352100
PubChem Substance ID:
24874334
NACRES:
NA.22

assay

97%

mp

218-222 °C (lit.)

SMILES string

BrC1=C(Br)C(=O)c2ccccc2C1=O

InChI

1S/C10H4Br2O2/c11-7-8(12)10(14)6-4-2-1-3-5(6)9(7)13/h1-4H

InChI key

PSMABVOYZJWFBV-UHFFFAOYSA-N

Categorías relacionadas

General description

2,3-Dibromo-1,4-naphthoquinone is a 2,3-disubstituted 1,4-naphthoquinone. It is a plumbagin derivative and an acaricide. It undergoes photochemical reaction with 2-methoxy-1-alkene to yield derivatives of 2-(2-alkanonyl)-1,4-naphthoquinone.

Application

2,3-Dibromo-1,4-naphthoquinone may be used in the synthesis of 3-[3-(2-carboxy-ethylsulfanyl)-1,4-dioxo-1,4-dihydro-naphthalen-2-ylsulfanyl]-propionic acid and NSC 95397 (a protein tyrosine phosphatase antagonist).

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Vincent P Peyregne et al.
Molecular cancer therapeutics, 4(4), 595-602 (2005-04-14)
Cdc25 phosphatases are important in cell cycle control and activate cyclin-dependent kinases (Cdk). Efforts are currently under way to synthesize specific small-molecule Cdc25 inhibitors that might have anticancer properties. NSC 95397, a protein tyrosine phosphatase antagonist from the National Cancer
Chi-Hoon Lee et al.
Journal of microbiology and biotechnology, 18(2), 314-321 (2008-03-01)
Acaricidal effects of materials derived from Diospyros kaki roots against Dermatophagoides farinae and D. pteronyssinus were assessed using impregnated fabric disk bioassay and compared with that of the commercial benzyl benzoate. The observed responses varied according to dosage and mite
A new method of ?-keto alkyl chain introduction into 1, 4-naphthoquinone.
Maruyama K, et al.
Chemistry Letters (Jpn), 13(3), 371-374 (1984)
A one-pot synthesis of 1, 4-naphthoquinone-2, 3-bis-sulfides catalysed by a commercial laccase.
Wellington KW, et al.
Green Chemistry, 14(9), 2567-2576 (2012)
Xiao-Fei Shang et al.
Scientific reports, 8(1), 1609-1609 (2018-01-27)
As important secondary plant metabolites, naphthoquinones exhibit a wide range of biological activities. However, their potential as sustainable alternatives to synthetic acaricides has not been studied. This study for the first time investigates the acaricidal activity of naphthoquinones against Psoroptes

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