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103594

Sigma-Aldrich

1-Nitronaphthalene

99%

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About This Item

Empirical Formula (Hill Notation):
C10H7NO2
CAS Number:
86-57-7
Molecular Weight:
173.17
Beilstein:
1867714
EC Number:
201-684-5
MDL number:
MFCD00003913
UNSPSC Code:
12352100
PubChem Substance ID:
24846612
NACRES:
NA.22

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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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.

Signal Word

Warning

Hazard Statements

H228,H302,H411

Hazard Classifications

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

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ5070
STBH5089
STBH4987
STBG7793
STBF8099V

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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
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
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
Myong Gyong Lee et al.
American journal of respiratory cell and molecular biology, 38(3), 300-309 (2007-09-29)
1-Nitronaphthalene (1-NN) and ozone are cytotoxic air pollutants commonly found as components of photochemical smog. The mechanism of toxicity for 1-NN involves bioactivation by cytochrome P450s and subsequent adduction to proteins. Previous studies have shown that 1-NN toxicity in the
J Azmi et al.
Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals, 10(6), 401-416 (2005-11-26)
Metabolic fingerprints, in the form of patterns of high-concentration endogenous metabolites, of 1-nitronaphthalene (NN)-induced lung toxicity have been elucidated in bronchoalveolar lavage fluid (BALF), urine, blood plasma, and intact lung and liver tissue using NMR spectroscopy-based metabolic profiling. A single
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