86-57-7

Usage

Uses

Used in Chemical Research:
1-Nitronaphthalene is used as a research compound for studying excited state dynamics in nonpolar, aprotic, and protic solvents. This helps scientists understand its behavior and properties in different environments.
Used in Environmental and Health Studies:
As a component of diesel exhaust, 1-Nitronaphthalene is used in studies related to environmental pollution and its effects on health, particularly its acute liver and lung toxicity in rodents.
Used in Mutagenicity Studies:
1-Nitronaphthalene, being a nitroaromatic compound, is used in mutagenicity studies to understand its potential to cause genetic mutations and its presence in everyday products such as polymers, dyes, and drugs.
Used in Pharmaceutical and Chemical Industries:
The mutagenicity and cytotoxic properties of 1-Nitronaphthalene make it a compound of interest in the pharmaceutical and chemical industries for the development of new drugs and chemical processes.

Biochem/physiol Actions

1-Nitronaphthalene binds covalently to protein and forms adducts in the rat airway epithelium in vivo.

Safety Profile

Poison by intraperitoneal route. Mutation data reported. A skin, eye, and mucous membrane irritant. Flammable solid and combustible liquid when exposed to heat or flame. To fight fire, use CO2, dry chemical, or water spray. Explosive reaction with nitric acid + sulfuric acid above 60°C. Forms a sensitive explosive mixture with tetranitromethane. When heated to decomposition it emits toxic fumes of NOx. See also 2-NITRONAPHTHALENE and NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

Purification Methods

Fractionally distil 1-nitronaphthalene under reduced pressure, then crystallise it from EtOH, aqueous EtOH or heptane. Chromatograph it on alumina with *benzene/pet ether as eluent. It sublimes in vacuo. The 1:1 picrate complex has m 72o (from EtOH). [Beilstein 5 H 553, 5 III 1593, 5 IV 1673.]

InChI:InChI=1/C10H7NO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H

Upstream product

• 91-20-3 naphthalene 
• 64-17-5 ethanol 
• 29809-14-1 5-nitro-1,2,3,4-tetrahydronaphthalene 
• 3272-91-1 5-nitro-[1]naphthylamine 
• 606-57-5 1-nitro-2-naphthylamine 
• 776-34-1 1-amino-4-nitronaphthalene 
• 134-32-7 1-amino-naphthalene 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 100-25-4 para-dinitrobenzene 
• 509-14-8 tetranitromethane 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 100-39-0 benzyl bromide 
• 74087-85-7 3,3-dimethyldioxirane 
• 100-44-7 benzyl chloride 

Downstream Products

• 2216-68-4 N-methylnaphthalen-1-amine 
• 6625-54-3 5-nitro-1-chloromethylnaphthalene 
• 134-32-7 1-amino-naphthalene 
• 81-77-6 6,15-dihydroanthrazine-5,9,14,18-tetrone 
• 118-44-5 1-N-ethylnaphthylamine 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 65-85-0 benzoic acid 
• 90-30-2 N-phenyl-1-naphthylamine 
• 85-44-9 phthalic anhydride 
• 136918-14-4 phthalimide 
• 41704-95-4 2,3-dioxo-indoline-4-carboxylic acid 
• 65399-18-0 4-nitrophthalide 
• 603-11-2 3-nitrophthalic acid 
• 509-14-8 tetranitromethane 

Relevant academic research and scientific papers

Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid

The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the ?NO2 radical is the active species.

Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium

Regardless of the sustainable development path, today, there are highly demanded chemical productions still operating that bear environmental and technological risks inherited from the previous century. The fabrication of nitro compounds, and nitroarenes in particular, is traditionally associated with acidic wastes formed in nitration reactions exploiting mixed acids. However, nitroarenes are indispensable for industrial and military applications. We faced the challenge and developed a greener, safer, and yet effective method for the production of nitroaromatics. The proposed approach comprises the application of an eco-friendly nitrating agent, namely dinitrogen pentoxide (DNP), in the medium of liquefied 1,1,1,2-tetrafluoroethane (TFE) - one of the most non-hazardous Freons. Importantly, the used TFE is not emitted into the atmosphere but is effortlessly recondensed and returned into the process. DNP is obtainedviathe oxidation of dinitrogen tetroxide with ozone. The elaborated method is characterized by high yields of the targeted nitro arenes, mild reaction conditions, and minimal amount of easy-to-utilize wastes.

Microwave-induced surface-mediated highly efficient regioselective nitration of aromatic compounds: Effects of penetration depth

Surface mediated highly regioselective nitration of aromatic compounds under diverse microwave-induced conditions was investigated in this work. The effects of the penetration depth of the surfaces were found to be more crucial than other dielectric parameters. Despite significant progress of microwave-induced reactions, no reports have examined the penetration depth of the surfaces used in these processes.

Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer

A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.

Selective preparation method of copper-catalyzed alpha-nitronaphthalene

The invention relates to a selective preparation method of copper-catalyzed alpha-nitronaphthalene, which comprises the following steps: dissolving naphthalene and nitric acid in an organic solvent toform a homogeneous solution, adding a copper catalyst, reacting at 0-50 DEG C for 0.5-10 hours, and carrying out after-treatment to obtain alpha-nitronaphthalene. According to the invention, copper is used as the catalyst, the synthesis process reduces the usage amount of acid, the operation is simple, the conditions are mild, the reaction time is short, the selectivity to alpha-nitronaphthaleneis very high, the supported copper catalyst can be recycled through centrifugal separation, the catalytic activity is high, the reaction raw materials are cheap and easily available. The method is a novel efficient preparation method.

Synthesis method of aromatic nitro-compound

The invention discloses a synthesis method of an aromatic nitro-compound. The synthesis method is characterized in that the aromatic nitro-compound is obtained by taking an aromatic amino-compound asa raw material and performing an oxidation reaction on the aromatic amino-compound and peroxytrifluoroacetic acid. The target aromatic nitro-compound is obtained by taking the aromatic amino-compoundas the raw material and performing the oxidation reaction on the aromatic amino-compound and peroxytrifluoroacetic acid; the synthesis method is high in yield, wide in application range, simple in operation and little in environmental pollution, therefore, the synthesis method is a good and ideal method for preparing the aromatic nitro-compound.

2-Methyl-1,3-disulfoimidazolium polyoxometalate hybrid catalytic systems as equivalent safer alternatives to concentrated sulfuric acid in nitration of aromatic compounds

Ionic liquid-derived polyoxometalate salts [mdsim]3[PM12O40] (where M?=?W and Mo) of two heteropolyacids H3PW12O40.nH2O and H3PMo12O40.nH2O were synthesized using 2-methyl-1,3-disulfoimidazolium chloride ([mdsim][Cl]) ionic liquid and the corresponding heteropolyacids. Three equivalents of [mdsim][Cl] were treated with the respective Keggin-structured heteropolyacids (one equivalent) in aqueous medium at room temperature to afford the water-stable ionic polyoxometalates as acidic solids. They were completely characterized using spectroscopic and other analytical techniques including thermal analysis and Hammett acidity studies. The inherent Br?nsted acidic properties of ─SO3H group of these polyoxometalate salts were studied for the nitration of aromatic compounds with 69% HNO3 at normal temperature and 80°C without use of any external concentrated sulfuric acid. These strongly acidic polyoxometalates display good recyclability and efficient reusability.

On/Off O2 Switchable Photocatalytic Oxidative and Protodecarboxylation of Carboxylic Acids

Photoredox catalysis in recent years has manifested a powerful branch of science in organic synthesis. Although merging photoredox and metal catalysts has been a widely used method, switchable heterogeneous photoredox catalysis has rarely been considered. Herein, we open a new window to use a switchable heterogeneous photoredox catalyst which could be turned on/off by changing a simple stimulus (O2) for two opponent reactions, namely, oxidative and protodecarboxylation. Using this strategy, we demonstrate that Au@ZnO core-shell nanoparticles could be used as a switchable photocatalyst which has good catalytic activity to absorb visible light due to the localized surface plasmon resonance effect of gold, can decarboxylate a wide range of aromatic and aliphatic carboxylic acids, have multiple reusability, and are a reasonable candidate for synthesizing both aldehydes/ketones and alkane/arenes in a large-scale set up. Some biologically active molecules are also shown via examples of the direct oxidative and protodecarboxylation which widely provided pharmaceutical agents.

Bismuth nitrate as a source of nitro radical in ipso-nitration of carboxylic acids

Aromatic nitro compounds are extensively used in synthetic chemistry. We disclose a new approach to obtain nitroarenes regioselectively starting from carboxylic acids under acid-free reaction conditions.