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510300

Sigma-Aldrich

2-Bromo-1,4-naphthoquinone

98%

Synonyme(s) :

2-Bromo-1,4-dihydronaphthalene-1,4-dione, 2-Bromo-1,4-naphthalenedione, 2-Bromo-p-naphthoquinone, 3-Bromo-1,4-naphthoquinone, 3-Bromonaphthoquinone

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About This Item

Formule empirique (notation de Hill):
C10H5BrO2
Numéro CAS:
2065-37-4
Poids moléculaire :
237.05
Numéro MDL:
MFCD00629301
Code UNSPSC :
12352100
ID de substance PubChem :
24873493
Nomenclature NACRES :
NA.22

Pureté

98%

Pf

131-133 °C (lit.)

Chaîne SMILES 

BrC1=CC(=O)c2ccccc2C1=O

InChI

1S/C10H5BrO2/c11-8-5-9(12)6-3-1-2-4-7(6)10(8)13/h1-5H

Clé InChI

KJOHPBJYGGFYBJ-UHFFFAOYSA-N

Description générale

2-Bromo-1,4-naphthoquinone (BrQ) is a 1,4-naphthoquinone derivative that can be prepared by the bromination of 1-naphthol using N-bromosuccinimide. Its efficacy as an antifeedant against the cabbage looper, Trichoplusia ni has been evaluated.2 The reaction of BrQ with xanthene under photochemical conditions has been investigated. A report suggests that the replacement of 2-methyl-1,4-naphthoquinone with BrQ enhances its ability to produce hydrogen peroxide which can be employed for cancer treatment.

Application

2-Bromo-1,4-naphthoquinone may be used in the preparation of:
  • benzo[f]indolequinones
  • 2-azido-1,4-naphthoquinone
  • 2-allyl-3-bromo-1,4-naphthoquinone
  • 2-(3-indolyl)-1,4-naphthoquinones

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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The Photochemical Reaction of 1,4-Naphthoquinone Derivatives with Hydrogen Donors.
Maruyama K and Arakawa S.
Bulletin of the Chemical Society of Japan, 47(8), 1960-1966 (1974)
Padmakar A Suryavanshi et al.
Organic & biomolecular chemistry, 8(15), 3426-3436 (2010-06-10)
The CAN-catalyzed three-component between reaction between primary amines, beta-dicarbonyl compounds and naphthoquinones or 2-bromonaphthoquinones afforded, respectively, 5-hydroxybenzo[g]indoles and benzo[f]indole-4,9-diones, the former of which were transformed into tetracyclic azepino[1,2-a]benzo[g]indole systems through a gamma-alkylation/ring-closing metathesis sequence.
Tiago T Guimarães et al.
European journal of medicinal chemistry, 63, 523-530 (2013-03-29)
Continuing our screening program for novel anti-parasite compounds, we synthesized seven 1,4-naphthoquinones coupled to 1,2,3-triazoles, five nor-β-lapachone-based 1,2,3-triazoles and ten α-lapachone-based 1,2,3-triazoles. These and other naphthoquinonoid compounds were evaluated for their activity against promastigote forms of antimony-sensitive and -resistant strains
Stereoselective synthesis of deoxy analogues of the 3C-protease inhibitor thysanone.
Brimble MA and Elliott RJR
Tetrahedron, 58(1), 183-189 (2002)
F S Graciani et al.
Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas, 45(8), 701-710 (2012-05-16)
Apatone™, a combination of menadione (2-methyl-1,4-naphthoquinone, VK3) and ascorbic acid (vitamin C, VC) is a new strategy for cancer treatment. Part of its effect on tumor cells is related to the cellular pro-oxidative imbalance provoked by the generation of hydrogen
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