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103594

Sigma-Aldrich

1-Nitronaphthalene

99%

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Empirical Formula (Hill Notation):
C10H7NO2
CAS Number:
Molecular Weight:
173.17
Beilstein/REAXYS Number:
1867714
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

solid

bp

304 °C (lit.)

mp

53-57 °C (lit.)

solubility

H2O: insoluble
alcohol: soluble
carbon disulfide: freely soluble
chloroform: soluble
diethyl ether: freely soluble

density

1.223 g/mL at 25 °C (lit.)

SMILES string

[O-][N+](=O)c1cccc2ccccc12

InChI

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

InChI key

RJKGJBPXVHTNJL-UHFFFAOYSA-N

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1 of 4

This Item
185760117870W319309
1-Nitronaphthalene 99%

103594

1-Nitronaphthalene

1-Chloro-2-nitrobenzene 99%

185760

1-Chloro-2-nitrobenzene

trans-Anethole 99%

117870

trans-Anethole

1-Methylnaphthalene ≥95%

W319309

1-Methylnaphthalene

solubility

H2O: insoluble, carbon disulfide: freely soluble, diethyl ether: freely soluble, alcohol: soluble, chloroform: soluble

solubility

alcohol: soluble, benzene: soluble, diethyl ether: soluble, water: insoluble

solubility

H2O: very slightly soluble, acetone: soluble, alcohol: freely soluble, benzene: soluble, carbon disulfide: soluble, chloroform: miscible, diethyl ether: miscible, ethyl acetate: soluble, petroleum ether: soluble

solubility

-

form

solid

form

solid

form

solid or liquid

form

liquid

bp

304 °C (lit.)

bp

246 °C (lit.)

bp

234-237 °C (lit.)

bp

240-243 °C (lit.)

mp

53-57 °C (lit.)

mp

31-33 °C (lit.)

mp

20-21 °C (lit.)

mp

−22 °C (lit.)

density

1.223 g/mL at 25 °C (lit.)

density

1.348 g/mL at 25 °C (lit.)

density

0.988 g/mL at 25 °C (lit.)

density

1.001 g/mL at 25 °C (lit.)

General description

1-Nitronaphthalene is a mutagenic nitroaromatic compound present in diesel exhaust and it causes acute liver and lung toxicity in rodents. 1-Nitronaphthalene is a cytochrome P450-bioactivated, nonciliated bronchiolar epithelial (Clara) cell cytotoxicant .

Application

1-Nitronaphthalene was used to study excited state dynamics of 1-nitropthalene in nonpolar, aprotic and protic solvents.

Biochem/physiol Actions

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

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Flam. Sol. 2

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Christian Reichardt et al.
The Journal of chemical physics, 131(22), 224518-224518 (2009-12-17)
The electronic energy relaxation of 1-nitronaphthalene was studied in nonpolar, aprotic, and protic solvents in the time window from femtoseconds to microseconds. Excitation at 340 or 360 nm populates the Franck-Condon S(1)(pipi( *)) state, which is proposed to bifurcate into
J M Sauer et al.
Toxicology letters, 90(1), 19-27 (1997-01-15)
1-Nitronaphthalene is a mutagenic particulate of diesel exhaust which causes acute liver and lung toxicity in rodents. The studies presented here describe morphological changes in the lung and liver at several time intervals following a single injection of 1-nitronaphthalene (100
K el-Bayoumy et al.
Carcinogenesis, 6(4), 505-507 (1985-04-01)
A method was developed for the analysis of 1-nitronaphthalene, 1-nitropyrene, and 6-nitrochrysene in mainstream cigarette smoke, using [14C]1-nitronaphthalene, [14C]1-nitropyrene, and [14C]6-nitrochrysene as tracers and internal standards. Cigarette smoke condensate was collected and the appropriate fractions containing the labelled standards were
Ching Yu Lin et al.
Proteomics, 6(3), 972-982 (2006-02-03)
Naphthalene and 1-nitronaphthalene are ambient air pollutants, which undergo P450-dependent bioactivation in the lung. Reactive metabolites of naphthalene and 1-nitronaphthalene covalently bind to proteins, and the formation of covalent adducts correlates with airway epithelial cell injury in rodent models. These
Gregory L Baker et al.
Toxicological sciences : an official journal of the Society of Toxicology, 77(1), 135-141 (2003-11-06)
The mechanisms of toxicant-mediated lung injury and repair are influenced by the considerable spatial heterogeneity that exists within the conducting airways of the lungs. As a result of this heterogeneity, significant differences and similarities in gene expression are observed throughout

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