You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Database of hazardous chemicals.

1-Nitronaphthalene (CHEM003900)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2014-09-17 20:01:34 UTC
Update Date2016-11-09 01:09:14 UTC
Accession NumberCHEM003900
Identification
Common Name1-Nitronaphthalene
ClassSmall Molecule
Description1-nitronaphthalene (1-NN) is a common air pollutant in urban areas. It can react with ozone and will form reactive electrophiles that have been shown to bind covalently to specific proteins. 1-Nitronaphthalene is synthesized by the action of a mixture of nitric and sulfuric acids on finely ground naphthalene. 1-nitronaphthalene is used as a chemical intermediate in the manufacture of dyes (drugs, perfumes, rubber chemicals, tanning agents and pesticides) and as a fluorescence quencher for mineral oils. 1-NN is also found in the gas phase of diesel exhaust, making it one of the more common airborne pollutants. It has been detected in some carbon blacks as well as in particulate exhaust of diesel engines and has been found at low concentrations in ambient air.
Contaminant Sources
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • Sludge Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Dye
  • Industrial Precursor/Intermediate
  • Lachrymator
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
alpha-NitronaphthaleneChEBI
NitrolChEBI
a-NitronaphthaleneGenerator
Α-nitronaphthaleneGenerator
Chemical FormulaC10H7NO2
Average Molecular Mass173.168 g/mol
Monoisotopic Mass173.048 g/mol
CAS Registry Number86-57-7
IUPAC Name1-nitronaphthalene
Traditional Namenitrol
SMILESO=N(=O)C1=CC=CC2=CC=CC=C12
InChI IdentifierInChI=1S/C10H7NO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H
InChI KeyRJKGJBPXVHTNJL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitronaphthalenes. These are polycyclic aromatic compounds containing a naphthalene moiety substituted by one or more nitro groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNitronaphthalenes
Direct ParentNitronaphthalenes
Alternative Parents
Substituents
  • 1-nitronaphthalene
  • Nitroaromatic compound
  • Organic nitro compound
  • C-nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Lung
  • Nasal Passages
Pathways
NameSMPDB LinkKEGG Link
Metabolic PathwaysNot AvailableNot Available
Homologous recombinationNot Availablemap03440
ApoptosisNot Availablemap04210
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceYellow needles or green-red to brown crystals.
Experimental Properties
PropertyValue
Melting Point61.5°C
Boiling Point304°C
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.043 g/LALOGPS
logP3.2ALOGPS
logP2.9ChemAxon
logS-3.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area45.82 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.83 m³·mol⁻¹ChemAxon
Polarizability16.86 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9600000000-bdf73b19a48ec1965ff9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9600000000-bdf73b19a48ec1965ff9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-2900000000-0140e7cd9d0b52504c9aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-33ee06a9c8b5b2d7d4a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-9c34bb8dbc81213babf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi0-1900000000-b7e76a0a748be5940337Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-b7779eb83652f78c0ed9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-e703c93ccd2f202675fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01b9-1900000000-244213ab51d311f2343bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-e4aa4846c14db133ae00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-e4aa4846c14db133ae00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0900000000-e4aa4846c14db133ae00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-7dd52f7617ae35e45cc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-7dd52f7617ae35e45cc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-7900000000-bc620efb4831b6318040Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-2900000000-4e9a24f4a3738ec10d6fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureInhalation
Mechanism of Toxicity1-Nitronaphthalene and its reactive products specifically targets the airway epithelium. Its toxicity is synergized by prior long-term ozone exposure. 1-NN appears to specifically target peroxiredoxin 6 and biliverdin reductase as well as the N-terminal region of calreticulin.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (1)
Uses/SourcesIndustrial intermediate, used in production of dyes, found in diesel exhast, air pollutant
Minimum Risk LevelNot Available
Health EffectsHealth effects: May cause eye, skin, respiratory tract and digestive tract irritation. Chronic exposure may cause cancer (based on animal studies).
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0062188
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID34104
PubChem Compound ID6849
Kegg Compound IDC14040
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21264431
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21420130
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21922113
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22894348
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23013142
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=9020398