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5522-43-0

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5522-43-0 Usage

Description

1-Nitropyrene (1-NP) is a nitro-polycyclic aromatic hydrocarbon (PAH) and a byproduct of incomplete combustion product from stationary combustion sources and in vehicle exhaust fumes.

Chemical Properties

1-Nitropyrene is a synthetic, light sensitive, yellow to orange-brown crystalline solid that is practically insoluble in water and soluble in diethyl ether, acetone, ethanol, benzene and toluene. It is not used for any commercial applications and is used only for research purposes, principally as a marker for exposure to nitro-polycyclic aromatic hydrocarbons from diesel exhaust.

Uses

1-Nitropyrene is the most abundant nitropolycylcic aromatic hydrocarbon found in exhaust from diesel engines with potent carcinogenic and mutagenic properties.

Application

1-Nitropyrene has been reported to use as a chemical photosensitizer in photocopy toners. It is available for research purposes as a reference material with different purities. ?

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).

Definition

ChEBI: 1-nitropyrene is a nitroarene that is pyrene substituted at the 1-position by a nitro group. A by-product of combustion, it is the predominant nitrated polycyclic aromatic hydrocarbon emitted in a diesel engine. It has a role as a carcinogenic agent. It derives from a hydride of a pyrene.

Synthesis Reference(s)

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

General Description

Yellow needles or prisms (from ethanol).

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.

Check Digit Verification of cas no

The CAS Registry Mumber 5522-43-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,5,2 and 2 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 5522-43:
(6*5)+(5*5)+(4*2)+(3*2)+(2*4)+(1*3)=80
80 % 10 = 0
So 5522-43-0 is a valid CAS Registry Number.
InChI:InChI=1/C5H8N4S/c1-2-3-10-5-7-4(6)8-9-5/h2H,1,3H2,(H3,6,7,8,9)

5522-43-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Nitropyrene

1.2 Other means of identification

Product number -
Other names 1-nitro-pyrene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5522-43-0 SDS

5522-43-0Relevant articles and documents

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

Wang, Huimin,Hasegawa, Kiyoshi,Kagaya, Shigehiro

, p. 1923 - 1936 (1999)

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.

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

Murai, Masahito,Nishinaka, Naoki,Kimura, Mizuki,Takai, Kazuhiko

, (2019/05/08)

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.

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

Frommer, Jennifer,Karg, Beatrice,Weisz, Klaus,Müller, Sabine

, p. 7663 - 7673 (2018/11/02)

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.

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

-

Paragraph 0078; 0079, (2018/09/11)

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.

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