ContaminantDB: 2-Nitrophenol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (10)XML

Record Information

Version

1.0

Creation Date

2009-08-10 21:31:10 UTC

Update Date

2026-03-31 19:17:15 UTC

Accession Number

CHEM002562

Identification

Common Name

2-Nitrophenol

Class

Small Molecule

Description

2-Nitrophenol is a phenolic compound that is used mainly to make dyes, paint coloring, rubber chemicals, and substances that kill molds. (4)

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
Sludge Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Industrial Precursor/Intermediate
Industrial/Workplace Toxin
Nitrite
Organic Compound
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2-Hydroxynitrobenzene	ChEBI
O-Hydroxynitrobenzene	ChEBI
O-Nitrophenol	ChEBI
2-Nitrophenol, ammonium salt	HMDB
Ortho-nitrophenol	HMDB
2-Nitrophenol, sodium salt	HMDB

Chemical Formula

C₆H₅NO₃

Average Molecular Mass

139.109 g/mol

Monoisotopic Mass

139.027 g/mol

CAS Registry Number

88-75-5

IUPAC Name

2-nitrophenol

Traditional Name

o-nitrophenol

SMILES

OC1=CC=CC=C1[N+]([O-])=O

InChI Identifier

InChI=1S/C6H5NO3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H

InChI Key

IQUPABOKLQSFBK-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

mononitrophenol (CHEBI:16260 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Light yellow solid.

Experimental Properties

Property	Value
Melting Point	44.8°C
Boiling Point	Not Available
Solubility	2.5 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

Predicted Properties

Property	Value	Source
Water Solubility	4.25 g/L	ALOGPS
logP	1.91	ALOGPS
logP	1.61	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.05 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.36 m³·mol⁻¹	ChemAxon
Polarizability	12.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9600000000-f334730ebce29cc98fdc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0a4i-0900000000-c41839802d48c97c72b7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0a4i-0900000000-465b86a7fa9c91aea091	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0a4i-0900000000-ceb07f366862a609f086	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0a4r-0900000000-3d0f30b23eeba81f1048	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-052r-0900000000-1da0c5d7dfec9c468340	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-052r-0900000000-d696815345f1828530d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-0e903cf94b3c53ac4aa7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-4ba5e7ff168121879afd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-4900000000-5a658d75ea75304f6bd6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-00733f70f7b16c0d705d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-05d7e7d651eeffdea56b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002r-4900000000-412df114be028c848fda	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-9400000000-b9d470aedfc9324e848b	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (4) ; inhalation (4) ; dermal (4) ; eye contact (4).

Mechanism of Toxicity

The 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)

Metabolism

Nitrophenol may be absorbed following ingestion, inhalation, or dermal exposure. The major metabolic route for nitrophenols is conjugation, with the resultant formation of either glucuronide or sulfate conjugates. Conjugates are more polar than the parent compounds and therefore are easier to excrete in the urine. (4)

Toxicity Values

LD50: 334 mg/kg (Oral, Rat) (5) LD50: 378 mg/kg (Intraperitoneal, Mouse) (5) LD50: 100 mg/kg (Intravenous, Dog) (5)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

2-Nitrophenol is used mainly to make dyes, paint coloring, rubber chemicals, and substances that kill molds. (4)

Minimum Risk Level

Not Available

Health Effects

Nitrophenols may cause methemoglobinemia. This is a disorder in which there is an abnormally high level of methemoglobin in the blood, resulting in a decrease in the amount of oxygen that can be carried to the tissues and organs. (4, 3)

Symptoms

Symptoms 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)

Treatment

Methemoglobinemia 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)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0245260

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID