Skip to Content
Merck
All Photos(1)

Documents

Safety Information

510300

Sigma-Aldrich

2-Bromo-1,4-naphthoquinone

98%

Synonym(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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C10H5BrO2
CAS Number:
2065-37-4
Molecular Weight:
237.05
MDL number:
MFCD00629301
UNSPSC Code:
12352100
PubChem Substance ID:
24873493
NACRES:
NA.22

Assay

98%

mp

131-133 °C (lit.)

SMILES string

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

InChI key

KJOHPBJYGGFYBJ-UHFFFAOYSA-N

General description

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

510300-VAR:
510300-10G:
510300-BULK:
510300-100G:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service