5522-43-0

Basic information

• Product Name: 1-Nitropyrene
• Synonyms: 3-Nitropyrene;Pyrene, 1-nitro-;23264, 1-Nitropyrene (purity);NITROPYRENE;1-NITROPYRENE (100UG/ML IN TOLUENE);1-NITROPYRENE 98+%;Nitropyrene, Mono-, Di-, Tri- Tetra, isomers;1-Nitropyrene,99%
• CAS NO: 5522-43-0
• Molecular Formula: C₁₆H₉NO₂
• Molecular Weight: 247.25
• EINECS: 226-868-2
• Product Categories: Pyrenes;Alphabetic;Environmental CRM;N;NA - NIApplication CRMs;Nitro-PAH
• Mol File: 5522-43-0.mol

Chemical Properties

• Melting Point: 153-155 °C(lit.)
• Boiling Point: 390.29°C (rough estimate)
• Flash Point: 223.5ºC
• Appearance: Yellow acicular crystallization
• Density: 1.1699 (rough estimate)
• Vapor Pressure: 1.28E-05mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly, Heated), Ethyl Acetate (Slightly, Heated)
• BRN: 1882811
• CAS DataBase Reference: 1-Nitropyrene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Nitropyrene(5522-43-0)
• EPA Substance Registry System: 1-Nitropyrene(5522-43-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 40-20/21/22
• Safety Statements: 22-36/37/39-45-36/37
• WGK Germany: 3
• RTECS: UR2480000
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 5522-43-0(Hazardous Substances Data)

Usage

Uses

1-Nitropyrene is used as a chemical photosensitizer in the application industry of photocopy toners. It serves as a marker for exposure to nitro-polycyclic aromatic hydrocarbons from diesel exhaust, highlighting its role in environmental and health research.
Used in Environmental and Health Research:
1-Nitropyrene is used as a reference material for research purposes, particularly in studying the effects of exposure to nitro-polycyclic aromatic hydrocarbons from diesel exhaust. Its potent carcinogenic and mutagenic properties make it a significant concern for public health and environmental safety.
Used in Chemical Research:
1-Nitropyrene is available for research purposes as a reference material with different purities, aiding in the study of its chemical properties and potential applications in various fields.

Preparation

The synthesis of 1-nitropyrene by heating pyrene with nitric acid in acetic acid at 50 °C (Boit, 1965). 1-Nitropyrene was also produced in a mixture with dinitropyrenes following the addition of potassium nitrite to pyrene in diethyl ether (Prager & Jacobson, 1922).

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 1811, 1971 DOI: 10.1021/ja00736a057

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1-Nitropyrene may be sensitive to prolonged exposure to light. Reacts with ethanolic potassium hydroxide. Also reacts with zinc powder and ethanol with catalytic amounts of ammonium chloride or ammonia .

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 1-Nitropyrene emits toxic fumes of NOx.

Fire Hazard

Flash point data for 1-Nitropyrene are not available; however, 1-Nitropyrene is probably combustible.

Biochem/physiol Actions

Potent mutagen, carcinogen, environmental pollutant.

Safety Profile

Confirmed carcinogen withexperimental carcinogenic, neoplastigenic, andtumorigenic data. Human mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.

Carcinogenicity

1-Nitropyrene is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

Environmental Fate

1-NP creates yellow needles in ethanol, and it has a melting point of 155 ℃. It is partially insoluble in water (0.02 mg l-1, 25 ℃); very soluble in diethyl ether; and soluble in acetone, ethanol, benzene, toluene, and tetrahydrofluorenone. 1-NP upon an estimated Koc value (soil adsorption coefficient normalized to the content of organic carbon) of 13 500 is immobile in soil and adsorb to sediment and solids from water. According to Henry’s law constant of 2.5× 10-8 atmcum mol1 and vapor pressure (8.3 ×10-8 mmHg at 25℃) volatilization from moist soil surfaces and water is not an important fate process. It is expected to exist solely in the particulate phase in the ambient atmosphere. Adsorptions to the particulate phase cause occurring photolysis in lower rate and decompose by wet and dry deposition. An estimated bioconcentration factor of 4100 suggests that its concentration in aquatic organisms is very high.

Toxicity evaluation

1-NP can generate aryl nitrenium ions by nitroreduction or K-region nitropyrene epoxides by ring oxidation. This chemical can form DNA adducts. Both nitroreduction and the hydrolysis of glucuronides are essential in generating mutagenic metabolites. Another mechanism of toxicity is superoxide radical generation. The activation of 1-NP to a bacterial mutagen has been attributed to nitroreduction. However, enzymes of mammalian and microbial systems can reduce it to products such as 2-aminofluorene and 4-aminobiphenyl that react with nucleic acid and can be further metabolized by O-acetylation to yield products that can react with C-8 of guanine.

InChI:InChI=1/C5H8N4S/c1-2-3-10-5-7-4(6)8-9-5/h2H,1,3H2,(H3,6,7,8,9)

Upstream product

• 129-00-0 pyrene 
• 1606-67-3 1-aminopyrene 
• 30269-04-6 1,8-diaminopyrene 
• 14923-84-3 1,6-diaminopyrene 
• 92821-64-2 1,3-diaminopyrene 
• 64-19-7 acetic acid 
• 7697-37-2 nitric acid 

Downstream Products

• 85628-24-6 1-nitro-2-hydroxypyrene 
• 38037-54-6 1,3-dibromopyrene 
• 91254-96-5 1-Nitropyren-4-ol 
• 1606-67-3 1-aminopyrene 
• 1732-28-1 8-acetoxy-1-nitropyrene 
• 1732-27-0 6-acetoxy-1-nitropyrene 
• 78751-40-3 pyren-1-yl acetate 
• 96168-26-2 1-Sulfanilamino-pyren 
• 174580-11-1 4-Nitro-(N-pyren-1-ylsulfamoyl)benzene 
• 174580-12-2 1-Ethoxycarbonyl-4-[p-(N-pyren-1-ylsulfamoyl)phenyl]semicarbazide 
• 1294391-67-5 N,N-di(4-benzamidophenyl)-1-aminopyrene 
• 1232690-46-8 N,N-di-(4-aminophenyl)-1-aminopyrene 
• 36171-39-8 1-pyrenyl azide 
• 1416070-74-0 C₃₇H₂₄N₂ 

Relevant articles and documents

Nitration of pyrene adsorbed on silica particles by nitrogen dioxide under simulated atmospheric conditions

Nitration of adsorbed pyrene on silica particles with nitrogen dioxide was studied under condition of room light in a simulated atmosphere. An induction period was present in the nitration process. Nitric acid formed on the silica particles acted as the catalyst, and the reaction proceeded autocatalytically. Electron-donating substituents promoted the reaction, while the electron-attracting substituents diminished it. An electrophilic nitration mechanism involving HNO2+ and HN2O4+ as electrophiles was proposed for the reaction. Nitration of adsorbed pyrene on silica particles with nitrogen dioxide was studied under condition of room light in a simulated atmosphere. An induction period was present in the nitration process. Nitric acid formed on the silica particles acted as the catalyst, and the reaction proceeded autocatalytically. Electron-donating substituents promoted the reaction, while the electron-attracting substituents diminished it. An electrophilic nitration mechanism involving HNO2+ and HN2O4+ as electrophiles was proposed for the reaction.

The nitration of pyrene adsorbed on silica particles by nitrogen dioxide

Conversion of NO2, HNO2 gas, their mixture and a mixed gas of HNO2 and HNO3 on silica particles was investigated under simulated atmospheric conditions. Both HNO2 and HNO3 were detected as the products from conversion of NO2 on silica particles. However, unlike HNO3, which increased with conversion time, HNO2 underwent an increase-decrease time course due to the increased HNO3 further transformed HNO2 into NO+ on silica particles. Considering the catalytic effect of HNO3 and HNO2 on the nitration of pyrene adsorbed on silica particles by NO2, another electrophilic nitration path, analogous to the one that we previously reported, with NONO2/+ and NONO2/4+ as electrophiles was suggested. The two paths together gave an appropriate explanation for the catalytic effect of HNO2, HNO3 and their mixed gas on the nitration of the adsorbed pyrene by NO2. (C) 2000 Elsevier Science Ltd.

Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration

Despite the utility of 9-silafluorenes as functional materials and as building blocks, methods for efficient functionalization of their backbone are rare, probably because of the presence of easily cleavable C-Si bonds. Although controlling the regioselectivity of iridium-catalyzed direct borylation of C-H bonds is difficult, we found that bromination and nitration of 2-methoxy-9-silafluorene under mild conditions occurred predominantly at the electron-rich position. The resulting product having methoxy and bromo groups can be utilized as a building block for the synthesis of unsymmetrically substituted 9-silafluorene-containing π-conjugated molecules.

Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration

Despite the utility of 9-silafluorenes as functional materials and as building blocks, methods for efficient functionalization of their backbone are rare, probably because of the presence of easily cleavable C-Si bonds. Although controlling the regioselectivity of iridium-catalyzed direct borylation of C-H bonds is difficult, we found that bromination and nitration of 2-methoxy-9-silafluorene under mild conditions occurred predominantly at the electron-rich position. The resulting product having methoxy and bromo groups can be utilized as a building block for the synthesis of unsymmetrically substituted 9-silafluorene-containing ?-conjugated molecules.

Preparation and characterization of pyrene modified uridine derivatives as potential electron donors in RNA

Charge transfer across double stranded DNA was observed for the first time about 20 years ago, and ever since it has been the subject of a large number of studies. RNA has been hardly investigated in this regard, which not least is due to the lack of suitably functionalized ribonucleotide building blocks to serve as electron sources upon incorporation into oligoribonucleotides. We have synthesized two uridine derivatives carrying pyrene or dimethylaminopyrene linked to C5 of the nucleobase. The key to successful synthesis was the adaptation of Suzuki-Miyaura conditions to the coupling of the pyrene moiety with the ribonucleoside. Final decoration of the pyrenylated nucleosides with standard 5′-O- and 2′-O-protecting groups and subsequent 3′-O-phosphitylation delivered the building blocks for incorporation into RNA. Spectroscopic analysis of the two pyrenylated uridines and of the accordingly modified oligonucleotides showed that in particular the dimethyaminopyrene functionalized nucleoside is a promising candidate as an electron source for RNA charge transport studies.

Diphenylpyrenylamine-functionalized polypeptides: Secondary structures, aggregation-induced emission, and carbon nanotube dispersibility

In this study we prepared - through ring-opening polymerization of γ-benzyl-l-glutamate N-carboxyanhydride (BLG-NCA) initiated by N,N-di(4-aminophenyl)-1-aminopyrene (pyrene-DPA-2NH2) - poly(γ-benzyl-l-glutamate) (PBLG) polymers with various degrees of polymerization (DP), each featuring a di(4-aminophenyl)pyrenylamine (DPA) luminophore on the main backbone. The secondary structures of these pyrene-DPA-PBLG polypeptides were investigated using Fourier transform infrared spectroscopy and wide-angle X-ray diffraction, revealing that the polypeptides with DPs of less than 19 were mixtures of α-helical and β-sheet conformations, whereas the α-helical structures were preferred for longer chains. Interestingly, pyrene-DPA-2NH2 exhibited weak photoluminescence (PL), yet the emission of the pyrene-DPA-PBLG polypeptides was 16-fold stronger, suggesting that attaching PBLG chains to pyrene-DPA-2NH2 turned on a radiative pathway for the non-fluorescent molecule. Furthermore, pyrene-DPA-2NH2 exhibited aggregation-caused quenching; in contrast, after incorporation into the PBLG segments with rigid-rod conformations, the resulting pyrene-DPA-PBLG polypeptides displayed aggregation-induced emission. Transmission electron microscopy revealed that mixing these polypeptides with multiwalled carbon nanotubes (MWCNTs) in DMF led to the formation of extremely dispersible pyrene-DPA-PBLG/MWCNT composites. The fabrication of MWCNT composites with such biocompatible polymers should lead to bio-inspired carbon nanostructures with useful biomedical applications.

Method for nitrating aromatic compound by using nitrate under the action of auxiliary agent

The invention discloses a method for nitrating an aromatic compound by using a nitrate under the action of an auxiliary agent, and provides an aromatic nitro compound preparation method, which comprises: in the presence of an external action and an auxiliary agent, carrying out a nitrating reaction on an aromatic compound and a metal nitrate or a hydrate thereof to obtain the aromatic nitro compound, wherein the external action can cause the physical and/or chemical property change of a substance, the auxiliary agent is a substance having water absorbing ability, the external action can be mechanical force or heating, and the mechanical force can be any one selected from compression, shearing, impacting, friction, stretching, bending and vibration. According to the present invention, the method does not require any solvents so as to avoid the generation of the waste liquid; the acidic substance is not used, such that the treatment is simple after the reaction is completed, and the equipment is not damaged; the added auxiliary agent can be theoretically recycled; and the method has extremely high conversion rate and extremely high selectivity, and can be used for the nitration of conventional aromatic compounds.

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)

Synthesizing method of OLED intermediate and semiconductor material 1-hydroxy pyrene

The invention discloses a synthesizing method of OLED intermediate and semiconductor material 1-hydroxy pyrene. The method comprises the following steps: adding pyrene and a solvent I to a reaction vessel; uniformly stirring; then adding a nitrosation agent; stirring under the temperature of 20-25 DEG C; adding water to the obtained product; separating out a solid; drying the separated-out solid to obtain 1-nitroso pyrene; mixing 1-nitroso pyrene and an alcohol solvent to obtain suspension; charging air or oxygen into the suspension; performing illumination reaction until 1-nitroso pyrene is completely reacted; adding BHT; concentrating under the temperature of 45-50 DEG C until the product is dry; then adding a recrystallizing solvent; heating until dissolved clarification is realized; cooling until the temperature is 20-25 DEG C; filtering; and drying a filter cake to obtain 1-hydroxy pyrene. With the adoption of the method, 1-hydroxy pyrene with purity not less than 99.1% can be obtained.

Effect of the blocked-sites phenomenon on the heterogeneous reaction of pyrene with N2O5/NO3/NO2

To clarify whether the blocking reaction sites problem has a significant impact on heterogeneous reactions, experiments contrasting the order of pyrene (PY) particles' exposure to N2O5-O3 or O3-N2O5 in a heterogeneous process were conducted. Additionally, PY particles were exposed to N2O5 (～8 ppm) in the presence of O3 (2.5-30 ppm) in a reaction chamber at ambient pressure and room temperature. Our results show that the phenomenon of blocking reaction sites may be ubiquitous on the surfaces of atmospheric aerosol particles, and the N2O5-initiated ionic electrophilic nitration may be promoted by NO3 radical-initiated heterogeneous reactions on the aerosol particle surface. We also found that the operative reaction mechanism strongly depends on the concentrations of the nitric oxides in the atmosphere. Our results provide an explanation as to why 2-nitropyrene (2-NPY), one of the most ubiquitous nitro-polyaromatic hydrocarbon pollutants that exists in both the gas and particle phases, was not observed in previous experiments on the heterogeneous reactions of PY and N2O5/NO3/NO2.