1-Nitropyrene

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.