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103594

Sigma-Aldrich

1-Nitronaphthalene

99%

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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

Quality Level

100

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

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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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
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
Bridget Boland et al.
The Journal of pharmacology and experimental therapeutics, 310(2), 546-554 (2004-04-15)
Studies in rodents have demonstrated the importance of cytochrome P450 monooxygenases in generating reactive metabolites that produce Clara cell injury. Pulmonary P450 activities in rodents are much higher than those in primates, raising the issue of relevance of rodent data
Ching Yu Lin et al.
Toxicology, 260(1-3), 16-27 (2009-05-26)
Naphthalene and close structural analogues have been shown to cause necrosis of bronchiolar epithelial cells in mice by both inhalation exposure and by systemic administration. Cancer bioassays of naphthalene in mice have demonstrated a slight increase in bronchiolar/alveolar adenomas in
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