17024-19-0

Usage

Uses

Used in Environmental Research:
3-Nitrophenanthrene is used as a subject of study in environmental research for understanding its mutagenic and cancer-causing properties. This research aims to assess the compound's environmental effects, toxicity, and bioaccumulation, which can contribute to the development of strategies for mitigating its harmful impacts.
Used in Photochemistry:
As a potential photosensitizer, 3-Nitrophenanthrene is used in photochemistry applications. Its ability to absorb light in the ultraviolet and visible spectrums makes it a candidate for various photochemical reactions and processes, such as solar energy conversion and photocatalytic degradation of pollutants.
Used in Toxicology Studies:
3-Nitrophenanthrene is used as a test compound in toxicology studies to investigate its effects on living organisms. These studies help in understanding the compound's potential health risks and inform regulatory measures to control its exposure and usage.
Used in Material Science:
3-Nitrophenanthrene's unique chemical properties, such as its aromatic structure and nitro group, make it a candidate for material science research. It could potentially be used in the development of new materials with specific properties, such as in the field of organic electronics or as a component in advanced composites. However, more research is needed to explore these possibilities and assess the safety and feasibility of such applications.

InChI:InChI=1/C14H9NO2/c16-15(17)12-8-7-11-6-5-10-3-1-2-4-13(10)14(11)9-12/h1-9H

Upstream product

• 85-01-8 phenanthrene 
• 54888-73-2 C₂₁H₁₉N₃O₄S 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 1694-20-8 trans-4-nitrostilbene 
• 586-78-7 para-nitrophenyl bromide 
• 100-13-0 4-nitrostyrene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 869624-53-3 (1E,3Z)-1-(4-methanesulfonyl-2-nitrobuta-1,3-dien-1-yl)naphthalene 

Downstream Products

• 1892-54-2 3-aminophenanthrene 

Relevant academic research and scientific papers

Efficient synthesis of 9-aryldihydrophenanthrenes by a cascade reaction involving arynes and styrenes

A mild, general, and transition-metal-free protocol for the synthesis of 9,10-dihydrophenanthrenes is reported. The aryne generated by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes an efficient cascade reaction initiated by the Diels-Alder reaction with the differently substituted styrenes leading to the formation of 9-aryl-9,10-dihydrophenanthrene derivatives in moderate to good yields.

Expeditious synthesis of helicenes using an improved protocol of photocyclodehydrogenation of stilbenes

An improved procedure has been developed for photodehydrocyclization of stilbenes for the synthesis of phenanthrenes and helicenes. This procedure involves the use of THF as a scavenger of hydriodic acid produced during iodine mediated photodehydrocyclization. The use of THF is advantageous due to its higher boiling point, lower cost and easy availability as compared to propylene oxide. The method is applied to synthesize a number of phenanthrenes and helicenes. ARKAT-USA, Inc.

From β-nitrothiophenes to ring-fused nitrobenzenes: An overall ring-enlargement process via a facile, aromatization-driven, thermal 6π electrocyclization

In prosecution of previous work on the thermal cyclization of 1-aryl-4-methanesulfonyl-2-nitro-3-phenylsulfonyl-1,3-butadienes (7), the 3-unsubstituted derivatives 8, deriving from the initial ring opening of 3-nitrothiophene (2), have been likewise found herein to undergo cyclization, followed by aromatization, in analogous mild experimental conditions, leading to the ring-fused homo- or heteroaromatic nitro derivatives 10. The concerted electrocyclic nature of the process is strongly supported by the outcome of tests based on the variation of the polarity of the solvent or of the electron density on the aryl of 8. Thus, the successful application of the process to the non-phenylsulfonyl-activated 8 significantly widens the scope of a synthetically valuable overall ring-opening/ring-closing procedure from nitrothiophenes. Support to the recently renewed interest in thermal 6π electrocyclizations as a tool for the construction of the benzene ring is furthermore provided.

The Formation of Monomeric and Dimeric Nitro Nitrates in the Reaction of Phenanthrene with Nitrogen Dioxide; X-Ray Crystal Structure of trans-10-Nitro-9,10-dihydrophenanthren-9-yl Nitrate

Reaction of phenanthrene (1) with nitrogen dioxide in benzene solution gives the dimeric nitro nitrate (3), trans and cis nitro nitrates (7) and (8), and 9-nitro- (4), 3-nitro- (5) and 1-nitro-pnenanthrene (6).The X-ray crystal structure of the trans nitro nitrate (7) is reported.The effect of the phenanthrene (1) concentration on product yields is reported.Gas-liquid chromatography results for the nitro nitrates (3) and (7) point to difficulties in using this technique for product analyses in reactions of phenanthrene (1) with nitrogen dioxide.