17024-17-8

Usage

Type of compound

Polycyclic aromatic hydrocarbon (PAH) derivative

Nitro group attachment

Attached to the phenanthrene structure

Primary use

Research chemical and synthesis of organic compounds

Mutagenic properties

Known to have mutagenic properties

Carcinogenic properties

Known to have carcinogenic properties

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

Upstream product

• 85-01-8 phenanthrene 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 91-22-5 quinoline 
• 609-73-4 o-nitroiodobenzene 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 7154-66-7 2-bromobenzoic acid chloride 
• 10034-09-0 1-methoxy-1,3-butadiene 
• 605-71-0 1,5-dinitronaphthalene 

Downstream Products

• 4176-53-8 1-aminophenanthrene 

Relevant academic research and scientific papers

Reactions of gas-phase phenanthrene under simulated atmospheric conditions

Rate constants for the gas-phase reactions of phenanthrene with OH radicals, NO3 radicals, and O3 have been determined at 296 ± 2 K and atmospheric pressure of air. The rate constants obtained (in cm3 molecule- 1 s-1 units) were (1.27 ± 0.23) x 10-11 for the OH radical reaction, (1.2 ± 0.4) x 10-13 for the NO3 radical reaction under atmospheric conditions, and (4.0 ± 1.0) x 10-19 for the O3 reaction. These rate constants indicate that the OH radical and NO3 radical reactions will be the dominant atmospheric loss processes for phenanthrene and that the overall atmospheric lifetime of gas-phase phenanthrene will be ≤1 day. Mutagenicity bioassays and chemical analyses of the products of the NO3 radical reaction and NO(x)-air photooxidation of phenanthrene were also conducted.

A novel application of the Diels-Alder reaction: nitronaphthalenes as normal electron demand dienophiles

Thermal reactions between nitronaphthalenes and butadienes were studied. It was demonstrated that these reactions are capable of undergoing the normal electron demand Diels-Alder reaction, with a variety of dienes affording the phenanthrene derivatives. The influence of the extension and type of substitution was also discussed. When the electron-withdrawing activation of the naphthalenic nucleus or the donor properties of the dienes were not enough, N-naphthylpyrroles were detected as main product, suggesting that a competitive reaction would probably take place. The results clearly confirmed the dienophilic nature of nitronaphthalenic double bonds and provided an alternative procedure for phenanthrene derivatives and N-naphthylpyrroles' synthesis. The relative reactivity of the reactants and the viability of the reactions were discussed from a theoretical point of view.

A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction

Herein we report a novel palladium-catalyzed reaction that results in phenanthrene derivatives using aryl iodides, ortho-bromoben-zoyl chlorides and norbornadiene in one pot. This dramatic transformation undergoes ortho-C–H activation, decarbonylation and subsequent a retro-Diels–Alder process. Pleasantly, this protocol has a wider substrate range, shorter reaction times and higher yields of products than previously reported methods.

Mechanical force under the action of the nitration of aromatic compounds of nitrate method (by machine translation)

The invention discloses a mechanical force under the action of the nitration of aromatic compounds of nitrate method. The invention provides a method for preparing aromatic nitro compounds, comprising the following steps: under the action of mechanical force, aromatic compound with a metal nitrate or its hydrate by the nitration reaction, to obtain the aromatic nitro compound; the mechanical fastener is machinery offers can cause material physical and/or chemical nature of the change of the external force. The mechanical force can be compression, shear, impact, friction, tensile, bending and vibration of any kind. The invention has the following advantages: without the use of any solvent, thereby avoiding the waste liquid produced; and without the use of the acidic substance, the reaction is complete after treatment is simple, without any damage to the apparatus; a very high conversion and selectivity, can be applied to the nitration of conventional aromatic compound. (by machine translation)

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.