159092-69-0

Basic information

• Product Name: 2,6-DINITROPHENANTHRENE
• Synonyms: 2,6-DINITROPHENANTHRENE
• CAS NO: 159092-69-0
• Molecular Formula: C14H8 N2 O4
• Molecular Weight: 268.24
• Mol File: 159092-69-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 411.39°C (rough estimate)
• Flash Point: 261.9°C
• Appearance: /
• Density: 1.3140 (rough estimate)
• Vapor Pressure: 6.52E-10mmHg at 25°C
• Refractive Index: 1.5910 (estimate)
• CAS DataBase Reference: 2,6-DINITROPHENANTHRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DINITROPHENANTHRENE(159092-69-0)
• EPA Substance Registry System: 2,6-DINITROPHENANTHRENE(159092-69-0)

Safety Data

• Hazardous Substances Data: 159092-69-0(Hazardous Substances Data)

Usage

Chemical classification

Nitropolycyclic aromatic hydrocarbons

Common use

Reference standard for analysis of environmental samples for PAHs

Toxicity

Highly toxic

Hazardous effects

Potent mutagen, carcinogen, and teratogen

Regulation

Strictly regulated, use and handling subject to strict safety protocols

Environmental release

Efforts to reduce and limit release to minimize harmful effects on human health and environment.

InChI:InChI=1/C14H8N2O4/c17-15(18)11-5-6-13-10(7-11)2-1-9-3-4-12(16(19)20)8-14(9)13/h1-8H

Upstream product

• 85-01-8 phenanthrene 

Relevant articles and documents

Di- and trinitrophenanthrenes: Synthesis, separation, and reduction property

Although nitrated polycyclic aromatic hydrocarbons (nitrated PAHs), specifically, dinitrated PAHs, have been indicated as potent mutagenic and carcinogenic environmental pollutants, only a few di- and trinitrophenanthrenes (DNPHs and TNPHs) have been reported up to the present time. Methods for the preparation of DNPHs and TNPHs by direct nitration of phenanthrene were established in this study. The reaction of phenanthrene with fuming nitric acid in acetic anhydride gave a complex mixture of DNPHs. Eleven DNPHs were isolated by using preparative HPLC with a total of 62.6% yield. Their chemical structures were determined using 1H NMR and electron impact mass spectrometry (EI-MS). The isolated DNPHs and their yields were 2,10-DNPH (14.2%), 1,10-DNPH (8.0%), 3,10-DNPH (6.9%), 3,6-DNPH (6.6%), 2,9- DNPH (5.3%), 1,6-DNPH (5.1%), 3,5-DNPH (4.6%), 4,9-DNPH (3.2%), 4,10-DNPH (3.1%), 1,5-DNPH (2.8%), and 2,6-DNPH (2.8%). Similarly, nine TNPHs were obtained from the nitrated reaction mixture of phenanthrene with fuming nitric acid without solvent: 3,6,9-TNPH (9.2%), 2,6,9-TNPH (9.0%), 1,6,9- TNPH (8.2%), 1,5,10-TNPH (9.0%), 2,6,9-TNPH (9.0%), 1,6,9-TNPH (4.0%), 1,7,9- TNPH (3.4%), 2,5,10-TNPH (2.5%), 2,6,10-TNPH (2.4%), 3,5,10-TNPH (1.8%), and 2,7,9-TNPH (0.2%) in 46.5% of the total yield. The reduction properties of the DNPHs and TNPHs were examined using cyclic voltammetry. The LUMO energy levels of the DNPHs and TNPHs calculated by the AM1 method were correlated to the first reduction potentials (E( 1/2 )). The coplanar or noncoplanar conformations of the nitro substituents to the phenanthrene ring system were also discussed.