31581-11-0

Basic information

• Product Name: 2,3-DI(CHLOROMETHYL)-1,4-DIHYDRONAPHTHALENE-1,4-DIONE
• Synonyms: 2,3-DI(CHLOROMETHYL)-1,4-DIHYDRONAPHTHALENE-1,4-DIONE;2,3-Bis(chloromethyl)-1,4-naphthoquinone
• CAS NO: 31581-11-0
• Molecular Formula: C₁₂H₈Cl₂O₂
• Molecular Weight: 255.1
• Mol File: 31581-11-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 377.6°Cat760mmHg
• Flash Point: 159.6°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 6.69E-06mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: 2,3-DI(CHLOROMETHYL)-1,4-DIHYDRONAPHTHALENE-1,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DI(CHLOROMETHYL)-1,4-DIHYDRONAPHTHALENE-1,4-DIONE(31581-11-0)
• EPA Substance Registry System: 2,3-DI(CHLOROMETHYL)-1,4-DIHYDRONAPHTHALENE-1,4-DIONE(31581-11-0)

Safety Data

• Hazardous Substances Data: 31581-11-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H8Cl2O2/c13-5-9-10(6-14)12(16)8-4-2-1-3-7(8)11(9)15/h1-4H,5-6H2

Upstream product

• 7647-01-0 hydrogenchloride 
• 50-00-0 formaldehyd 
• 64-19-7 acetic acid 
• 130-15-4 [1,4]naphthoquinone 

Downstream Products

• 89676-56-2 2,3-bis(hydroxymethyl)-1,4-naphthoquinone bis[N-(2-chloroethyl)carbamate] 
• 89676-55-1 2,3-bis(hydroxymethyl)-1,4-naphthoquinone bis(N-methylcarbamate) 
• 6531-35-7 2,3-dimethylanthraquinone 
• 74408-27-8 2,3-bis-(p-tolylthiomethyl)-1,4-naphthoquinone 

Relevant articles and documents

An original one-pot synthesis of dialkyl-substituted anthraquinones

2,3-Bis(chloromethyl)-1,4-naphthoquinone reacts with primary nitroalkanes in a one-pot synthesis to give a series of anthraquinones bearing two n-alkyl substituents at C-2 and C-3 in good yields. The reaction is shown to proceed by two consecutive SRN1 processes followed by base-promoted nitrous acid elimination, electrocyclic ring-closure and dehydrogenation. In comparison with the classical Diels-Alder reaction, the advantage of this route is the simplicity of starting-material preparation.

Anti-cancer effect of a novel 2,3-didithiocarbamate-substituted naphthoquinone as a tumor metabolic suppressor: In vitro and in vivo

Tumor cells reprogram their cellular metabolism by switching from oxidative phosphorylation to aerobic glycolysis to support aberrant cell proliferation. Suppressing tumor cell metabolism has become an attractive strategy for treating cancer patients. In this study, we identified a 2,3-didithiocarbamate-substituted naphthoquinone 3i that inhibited the proliferation of tumor cells by disturbing their metabolism. Compound 3i reduced cancer cell viability with IC50 values from 50 nM to 150 nM against HCT116, MCF7, MDA-MB231, HeLa, H1299 and B16 cells. Further, compound 3i was found to suppress ATP production in cultured cancer cells, inhibit the M2 isoform of pyruvate kinase (PKM2) which is a rate-limiting enzyme in the glycolytic pathway and block the subsequent transcription of the downstream genes GLUT1, LDH and CCND1. In addition, exposure to compound 3i significantly suppressed tumor growth in a B16 melanoma transplantation mouse model and a spontaneous breast carcinoma mouse model in vivo. The identification of compound 3i as a tumor metabolic suppressor not only offers a candidate compound for cancer therapy, but also provides a tool for an in-depth study of tumor metabolism.

Synthesis of 2,3-dialkylquinones by Bis-SRN1 methodology

Three series of complex dialkylquinones were prepared by reacting bis(chloromethyl)quinones with simple and more complex nitronate anions under electron transfer reaction conditions.