52431-61-5

Basic information

• Product Name: 5-chloro-8-hydroxy-6-methylnaphthalene-1,4-dione
• Synonyms: 1,4-naphthalenedione, 5-chloro-8-hydroxy-6-methyl-
• CAS NO: 52431-61-5
• Molecular Formula: C₁₁H₇ClO₃
• Molecular Weight: 222.6245
• Mol File: 52431-61-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 462.5°C at 760 mmHg
• Flash Point: 233.5°C
• Density: 1.492g/cm³
• Vapor Pressure: 3.55E-09mmHg at 25°C
• Refractive Index: 1.651
• CAS DataBase Reference: 5-chloro-8-hydroxy-6-methylnaphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chloro-8-hydroxy-6-methylnaphthalene-1,4-dione(52431-61-5)
• EPA Substance Registry System: 5-chloro-8-hydroxy-6-methylnaphthalene-1,4-dione(52431-61-5)

Safety Data

• Hazardous Substances Data: 52431-61-5(Hazardous Substances Data)

Upstream product

• 69945-29-5 5,8-Diacetoxy-2-acetyl-6,7-dibrom-4-chlor-3-methyl-1-naphthol 
• 69945-30-8 5,8-Diacetoxy-2-acetyl-4-chlor-3-methyl-1-naphthol 
• 108-31-6 maleic anhydride 
• 14472-14-1 4-bromo-3-methylphenol 
• 59-50-7 4-Chloro-3-methylphenol 

Downstream Products

• 75445-71-5 2-Benzyl-4-benzyloxy-8-methoxy-6-methyl-1-naphthol 
• 75445-77-1 1,5-Bis(benzyloxy)-4-methoxy-7-methylnaphthalin 
• 75445-72-6 4,8-Bis(benzyloxy)-6-methyl-1-naphthol 
• 75445-76-0 1-Benzyloxy-4,5-dimethoxy-7-methylnaphthalin 
• 75445-63-5 8-Benzyloxy-4-methoxy-6-methyl-1-naphthol 
• 75445-64-6 5-Benzyloxy-4-methoxy-7-methyl-1-naphthol 
• 75445-65-7 5-Benzyloxy-7-methyl-naphthalene-1,4-diol 
• 75445-69-1 4-Benzyloxy-8-methoxy-6-methyl-1-naphthol 
• 75445-84-0 5-Benzyl-5-methoxy-7-methyl-1,4-naphthochinon 
• 75445-60-2 5-(benzyloxy)-7-methylnaphthalene-1,4-dione 
• 17734-93-9 mamegakinone 
• 24456-79-9 5,5'-dihydroxy-7,7'-dimethyl-[2,2']binaphthalenylidene-1,4,1',4'-tetraone 
• 60548-89-2 5,5'-dihydroxy-4,4'-dimethoxy-7,7'-dimethyl-2,2'-binaphthylidene-1,1'-quinone 
• 89475-20-7 1-Benzyloxy-4-chlor-5,8-dimethoxy-3-methylnaphthalin 

Relevant articles and documents

Ebenaceae extractives. Part 11. The synthesis of 7-methyljuglone. A re-examination

The Friedel-Crafts reaction between maleic anhydride and 4-chloro-3-methylphenol yields, besides 8-chloro-5-hydroxy-7-methylnaphthoquinone 1, helminthosporin 5 and its 8-chloro derivative 6 and, after methylation, methyl (E)-β-(5-chloro-2-methoxy-4-methylbenzoyl)acrylate 4. Treatment of the chloronaphthoquinone 1 with tin(II) chloride in hydrochloric acid and tetrahydrofuran followed by iron(III) chloride converts it efficiently into 7-methyljuglone 2.

Cytotoxicity of synthesized 1,4-naphthoquinone analogues on selected human cancer cell lines

In an effort to establish new candidates with enhanced anticancer activity of 5-hydroxy-7-methyl-1,4-naphthoquinone scaffold (7-methyljuglone) previously isolated from the root extract of Euclea natalensis, a series of 7-methyljuglone derivatives have been synthesized and assessed for cytotoxicity on selected human cancer lines. These compounds were screened in vitro for anticancer activity on MCF-7, HeLa, SNO and DU145 human cancer cell lines by MTT assay. Most of them exhibited significant toxicity on cancer cell lines with lower IC50 values. The most potent derivative (19) exhibited the toxicity on HeLa and DU145 cell lines with IC50 value of 5.3 and 6.8 μM followed by compound (5) with IC50 value of 10.1 and 9.3 μM, respectively. Structure-activity relationship reveals that the fluoro substituents at position C-8 while hydroxyl substituents at C-2 and C-5 positions played an important role in toxicity.

New naphthoquinone derivatives against glioma cells

This work was aimed to the development of a set of new naphtoquinone derivatives that can act against glioma. The compounds were tested in order to find out their ability to inhibit the growth of glioma cells, and the results of these assays were correlated with electrochemical analysis and NMR-based reoxidation kinetic studies, suggesting that a redox mechanism underlies and may explain the observed biological behavior. In addition to a full description of the synthetic pathways, electrochemistry, NMR and single crystal X-ray diffraction data are provided.