159092-78-1

Basic information

• Product Name: 1,6,9-trinitrophenanthrene
• Synonyms: 1,6,9-Trinitrophenanthrene; phenanthrene, 1,6,9-trinitro-
• CAS NO: 159092-78-1
• Molecular Formula: C₁₄H₇N₃O₆
• Molecular Weight: 313.2219
• Mol File: 159092-78-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 565.6°C at 760 mmHg
• Flash Point: 291.3°C
• Density: 1.621g/cm³
• Vapor Pressure: 3.15E-12mmHg at 25°C
• Refractive Index: 1.786
• CAS DataBase Reference: 1,6,9-trinitrophenanthrene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6,9-trinitrophenanthrene(159092-78-1)
• EPA Substance Registry System: 1,6,9-trinitrophenanthrene(159092-78-1)

Safety Data

• Hazardous Substances Data: 159092-78-1(Hazardous Substances Data)

Usage

General Description

1,6,9-trinitrophenanthrene is a chemical compound with the molecular formula C18H9N3O6. It is a polycyclic aromatic hydrocarbon derivative that is a yellow crystalline solid at room temperature. 1,6,9-trinitrophenanthrene is a powerful explosive and is highly sensitive to heat and shock. It is commonly used in the production of explosives and propellants. Its explosive properties are attributed to its high nitrogen content and the presence of multiple nitro groups, which make it highly reactive. Due to its explosive nature, 1,6,9-trinitrophenanthrene is classified as a hazardous substance and should be handled with extreme caution.

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.