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1-Nitropyrene

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CAS:5522-43-0
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CAS:5522-43-0

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1-Nitropyrene 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:5522-43-0
MF:C16H9NO2
MW:247.25
EINECS:226-868-2
Product Categories:Alphabetic;Environmental CRM;N;NA - NIApplication CRMs;Nitro-PAH;Pyrenes
Mol File:5522-43-0.mol
1-Nitropyrene Structure
1-Nitropyrene Chemical Properties
Melting point 153-155 °C (lit.)
Boiling point 390.29°C (rough estimate)
density 1.1699 (rough estimate)
refractive index 1.5300 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Sparingly, Heated), Ethyl Acetate (Slightly, Heated)
color Yellow needles from MeCN
BRN 1882811
InChIKeyALRLPDGCPYIVHP-UHFFFAOYSA-N
CAS DataBase Reference5522-43-0(CAS DataBase Reference)
IARC2A (Vol. Sup 7, 46, 105) 2014
NIST Chemistry Reference1-Nitropyrene(5522-43-0)
EPA Substance Registry System1-Nitropyrene (5522-43-0)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 40-20/21/22
Safety Statements 22-36/37/39-45-36/37
WGK Germany 3
RTECS UR2480000
TSCA T
HazardClass IRRITANT
HS Code 29420000
Hazardous Substances Data5522-43-0(Hazardous Substances Data)
Toxicitymic-sat 2500 ng/plate GDIKAN 29,278,1981
Toxicitymmo-esc 3 mg/plate MUREAV 142,163,85
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
1-Nitropyrene Usage And Synthesis
Description1-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 Properties1-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.
Uses1-Nitropyrene is the most abundant nitropolycylcic aromatic hydrocarbon found in exhaust from diesel engines with potent carcinogenic and mutagenic properties.
Application1-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. ?
PreparationThe 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).
DefinitionChEBI: 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 DescriptionYellow needles or prisms (from ethanol).
Air & Water ReactionsInsoluble in water.
Reactivity Profile1-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 HazardACUTE/CHRONIC HAZARDS: When heated to decomposition 1-Nitropyrene emits toxic fumes of NOx.
Fire HazardFlash point data for 1-Nitropyrene are not available; however, 1-Nitropyrene is probably combustible.
Biochem/physiol ActionsPotent mutagen, carcinogen, environmental pollutant.
Safety ProfileConfirmed carcinogen withexperimental carcinogenic, neoplastigenic, andtumorigenic data. Human mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.
Carcinogenicity1-Nitropyrene is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental Fate1-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 evaluation1-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.
1-Nitropyrene Preparation Products And Raw materials
Preparation Products1-HYDROXYPYRENE
Tag:1-Nitropyrene(5522-43-0) Related Product Information
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