2-Nitrophenol (CED0008155)

Record Information
Version1.0
Creation Date2009-08-10 21:31:10 UTC
Update Date2026-08-23 11:50:05 UTC
Accession NumberCHEM002562
Identification
Common Name2-Nitrophenol
ClassSmall Molecule
Description
2-Nitrophenol belongs to the nitrophenols, a subclass of phenols within the organic compounds. This exogenous benzenoid has the formula C6H5NO3 and an average molecular weight of 139.11 g/mol. At room temperature, it exists as a solid. It is used primarily in the production of rubber chemicals, paint coloring, dyes, and substances that kill molds. The compound is found in or released from 41 recorded sources. These include aquatic systems and sediments such as freshwater, seawater, surface water, and groundwater, as well as drinking water and water supply sources including tap, bottled, and desalinated water. It is also present in wastewater, sanitation, and biosolids, including unspecified wastewater, industrial wastewater, mine wastewater, and wastewater treatment effluent. Additional sources include household cleaning and consumer products such as soap detergents, bleaching agents, tobacco smoke filters, cigar cigarettes, and perfumes within detergents and soaps. It is associated with food, food processing, and cookware, specifically the preparation of malt, wort, and wine or sparkling wine, as well as food preservation and fermentation processes for beer. Furthermore, it is found in electrical and electronic equipment, including antennas, amplifiers, electric switches, conductive bodies characterized by the conductive materials, and electrically stimulated smoking devices, among five other sources. Exposure routes include touch, oral, and inhalation. Recorded protein targets include the estrogen receptor (ESR1) and hemoglobin subunits alpha (HBA1) and beta (HBB). The nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to methemoglobin and hydrogen peroxide. This elevation of methemoglobin levels results in a condition called methemoglobinemia, which is characterized by tissue hypoxia because methemoglobin cannot bind oxygen.
Contaminant Type
  • Aromatic Hydrocarbon
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Nitrite
  • Organic Compound
  • PMT
  • Pollutant
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
2-HydroxynitrobenzeneChEBI
O-HydroxynitrobenzeneChEBI
O-NitrophenolChEBI
2-Nitrophenol, ammonium saltHMDB
Ortho-nitrophenolHMDB
2-Nitrophenol, sodium saltHMDB
Chemical FormulaC6H5NO3
Average Molecular Mass139.109 g/mol
Monoisotopic Mass139.027 g/mol
CAS Registry Number88-75-5
IUPAC Name2-nitrophenol
Traditional Nameo-nitrophenol
SMILESOC1=CC=CC=C1[N+]([O-])=O
InChI IdentifierInChI=1S/C6H5NO3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H
InChI KeyIQUPABOKLQSFBK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitrophenols. Nitrophenols are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassNitrophenols
Direct ParentNitrophenols
Alternative Parents
Substituents
  • Nitrophenol
  • Nitrobenzene
  • Nitroaromatic compound
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceLight yellow solid.
Experimental Properties
PropertyValue
Melting Point44.8°C
Boiling PointNot Available
Solubility2.5 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted Properties
PropertyValueSource
Water Solubility4.25 g/LALOGPS
logP1.91ALOGPS
logP1.61ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.05 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.36 m³·mol⁻¹ChemAxon
Polarizability12.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000i-9600000000-f334730ebce29cc98fdcNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-c41839802d48c97c72b7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-465b86a7fa9c91aea091Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-ceb07f366862a609f086Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4r-0900000000-3d0f30b23eeba81f1048Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-0900000000-1da0c5d7dfec9c468340Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-0900000000-d696815345f1828530d1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-0e903cf94b3c53ac4aa7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-4ba5e7ff168121879afdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01q9-4900000000-5a658d75ea75304f6bd6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-00733f70f7b16c0d705dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-05d7e7d651eeffdea56bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002r-4900000000-412df114be028c848fdaNot AvailableView Spectrum
MSMS Spectrumsplash10-000i-9400000000-b9d470aedfc9324e848bNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityThe nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen. (1, 3)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsSymptoms of methemoglobinemia include shortness of breath, cyanosis, mental status changes, headache, fatigue, exercise intolerance, dizziness and loss of consciousness. Severe methemoglobinemia may cause dysrhythmias, seizures, coma and death. (3)
TreatmentMethemoglobinemia can be treated with supplemental oxygen and methylene blue 1% solution at 1-2mg/kg administered intravenously slowly over five minutes followed by an IV flush with normal saline. Methylene blue restores the iron in hemoglobin to its normal (reduced) oxygen-carrying state. (3)
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
334.0mg/kgNot AvailableRatLD50OralexperimentalT14
378.0mg/kgNot AvailableMouseLD50IntraperitonealexperimentalT14
100.0mg/kgNot AvailableDogLD50IntravenousexperimentalT14
254.0Log mg/kg[140:450]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
3Irrigation waterAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
27Water CoolersAppliances, HVAC & refrigerantsNot Available
43Water heatersAppliances, HVAC & refrigerantsNot Available
50GroundwaterAquatic systems & sedimentsNot Available
51Surface waterAquatic systems & sedimentsNot Available
52SeawaterAquatic systems & sedimentsNot Available
53FreshwaterAquatic systems & sedimentsNot Available
70Stormwater runoffAutomotive & urban infrastructureNot Available
88Waterproofing spraysBuilding & ConstructionNot Available
115Drinking waterDrinking water & water supplyNot Available
116Tap waterDrinking water & water supplyNot Available
117Bottled waterDrinking water & water supplyNot Available
118Desalinated waterDrinking water & water supplyNot Available
181Ballast waterMarine, shipping & aquacultureNot Available
182Bilge waterMarine, shipping & aquacultureNot Available
468Industrial wastewaterWastewater, sanitation & biosolidsNot Available
470Wastewater treatment effluentWastewater, sanitation & biosolidsNot Available
475Mine wastewaterWastewater, sanitation & biosolidsNot Available
477Wastewater, unspecifiedWastewater, sanitation & biosolidsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
648Nitro DyesTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Endolysin structureClick to view 3D structureEndolysinP00720Enterobacteria phage T4Predicted (SEA)0.311397
Click to view 3D structureCystathionine beta-lyase MetCP06721Escherichia coli K-12Predicted (SEA)0.311397
Click to view 3D structureCatechol O-methyltransferaseP22734Rattus norvegicusPredicted (SEA)1.32344
Click to view 3D structureCatechol O-methyltransferaseQ99028Sus scrofaPredicted (SEA)0.467095
Click to view 3D structureATP-dependent molecular chaperone HSP82C4YTQ8Candida albicans (strain WO-1) (Yeast)Predicted (SEA)12.7673
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)140.051
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)29.8163
Click to view 3D structureGenome polyproteinP29990dengue virus type 2Predicted (SEA)8.48557
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)134.913
Transthyretin structureClick to view 3D structureTransthyretinP02766HumansPredicted (SEA)14.1686
G-protein coupled receptor 35 structureClick to view 3D structureG-protein coupled receptor 35Q9HC97HumansPredicted (SEA)12.6894
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)92.4849
Click to view 3D structureLarge T antigenP03070Simian virus 40Predicted (SEA)14.3243
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)124.014
Click to view 3D structureNonstructural protein 1Q194T2Influenza A virusPredicted (SEA)23.744
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)264.454
Click to view 3D structureHeat shock factor protein 1P38532Mus musculusPredicted (SEA)53.4824
Click to view 3D structureThioredoxin reductaseP61076Plasmodium falciparum 3D7Predicted (SEA)0.934191
Alpha-ketoglutarate-dependent dioxygenase FTO structureClick to view 3D structureAlpha-ketoglutarate-dependent dioxygenase FTOQ9C0B1HumansPredicted (SEA)15.4141
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)713.255
Dual specificity protein phosphatase 3 structureClick to view 3D structureDual specificity protein phosphatase 3P51452HumansPredicted (SEA)54.1831
Click to view 3D structurePutative nitroreductaseQ4A0P1Staphylococcus saprophyticus subsp. saprophyticus (strain ATCC 15305 / DSM20229 / NCIMB 8711 / NCTC 7292 / S-41)Predicted (SEA)0.778492
Arylsulfatase structureClick to view 3D structureArylsulfataseP51691Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)Predicted (SEA)9.57545
Click to view 3D structureIntestinal-type alkaline phosphataseP24822Mus musculusPredicted (SEA)16.8154
Protein S100-A4 structureClick to view 3D structureProtein S100-A4P26447HumansPredicted (SEA)3.42537
Hemoglobin subunit alpha structureClick to view 3D structureHemoglobin subunit alphaP69905HumansKnownThe nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen. (A2450, L1613)
Hemoglobin subunit beta structureClick to view 3D structureHemoglobin subunit betaP68871HumansKnownThe nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen. (A2450, L1613)
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0245260
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-258
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNitrophenol
Chemspider ID13837787
ChEBI ID16260
PubChem Compound ID6947
Kegg Compound IDC01988
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23796307
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24347320
3. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.