1,4-Dinitroanthracene-9,10-dione

Base Information

• Chemical Name: 1,4-Dinitroanthracene-9,10-dione
• CAS No.: 66121-37-7
• Molecular Formula: C14H6N2O6
• DSSTox Substance ID: DTXSID20495853
• Nikkaji Number: J207.114B
• Mol file: 66121-37-7.mol

Synonyms:1,4-Dinitroanthracene-9,10-dione;66121-37-7;SCHEMBL5109566;DTXSID20495853

Chemical Property of 1,4-Dinitroanthracene-9,10-dione

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 298.02258592
• Heavy Atom Count: 22
• Complexity: 488

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C=CC(=C3C2=O)[N+](=O)[O-])[N+](=O)[O-]

Refernces

Synthesis of 1,4-Dinitroanthracene-9,10-dione. Stepwise Substitution of the Nitro Groups by Diamines Leading to 1-<(Aminoalkyl)amino>-4-nitroanthracene-9,10-diones and Unsymmetrical 1,4-Bis<(aminoalkyl)amino>anthracene-9,10-diones

10.1021/jo00308a030

The study focuses on the synthesis of 1,4-dinitroanthracene-9,10-dione (2) and its subsequent transformations using various diamines. The researchers explored two methods for synthesizing 2, one involving trifluoroacetic anhydride and hydrogen peroxide, and the other using trifluoroacetic acid and hydrogen peroxide. They then investigated the displacement of the nitro groups in 2 by different diamines, such as N,N-dimethylethylenediamine, 2-[(2-aminoethyl)amino]ethanol, and ethylenediamine, to produce monosubstituted and bis-substituted anthracene-9,10-dione derivatives. The study also examined the sequential displacements of the nitro substituents by diamines to prepare unsymmetrically substituted 1,4-bis[(aminoalkyl)amino]anthracene-9,10-diones. The products were characterized using various analytical techniques, including melting point determination, proton NMR, and mass spectrometry.