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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

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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

Quality Level

100

Assay

98%

mp

131-133 °C (lit.)

functional group

bromo
ketone

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000388799
0000365379
0000365379
0000388799
0000218095

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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
Stereoselective synthesis of deoxy analogues of the 3C-protease inhibitor thysanone.
Brimble MA and Elliott RJR
Tetrahedron, 58(1), 183-189 (2002)
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.
Lara G Freidus et al.
Molecules (Basel, Switzerland), 25(19) (2020-10-03)
Synthesis of a novel theranostic molecule for targeted cancer intervention. A reaction between curcumin and lawsone was carried out to yield the novel curcumin naphthoquinone (CurNQ) molecule (2,2'-((((1E,3Z,6E)-3-hydroxy-5-oxohepta-1,3,6-triene-1,7-diyl) bis(2-methoxy-4,1-phenylene))bis(oxy))bis(naphthalene-1,4-dione). CurNQ's structure was elucidated and was fully characterized. CurNQ was demonstrated
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)
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