ContaminantDB: 4-Nitrophenol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (12)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:23 UTC

Update Date

2026-03-31 19:11:21 UTC

Accession Number

CHEM000222

Identification

Common Name

4-Nitrophenol

Class

Small Molecule

Description

4-Nitrophenol is a phenolic compound that is used mainly to make fungicides and dyes, and to darken leather. It is also used in the synthesis of drugs such as paracetamol, phenetidine, and acetophenetidine. 4-Nitrophenol measurement in urine is used in biological monitoring for establishing the presence and magnitude of exposures to pesticides. (3) (Methods in Biotechnology, 2006,61-78) (22, 23)

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
Sludge Chemicals
Suspected Compounds – Schymanski Project
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

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

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Hydroxynitrobenzene	ChEBI
Niphen	ChEBI
p-Hydroxynitrobenzene	ChEBI
p-Nitrophenol	ChEBI
Paranitrophenol	ChEBI
PNP	ChEBI
Mononitrophenol	HMDB
1-Hydroxy-4-nitrobenzene	HMDB
4-Nitrophenol, (18)O-labeled CPD	HMDB
4-Nitrophenol, 1-(13)C-labeled CPD	HMDB
4-Nitrophenol, manganese (2+) salt	HMDB
4-Nitrophenol, silver(2+) salt	HMDB
4-Nitrophenol, sodium salt, (2:1), dihydrate	HMDB
4-Nitrophenol, tin (4+) salt	HMDB
4-Nitrophenol, 2,6-(13)C2-labeled CPD	HMDB
4-Nitrophenol, 2-(14)C-labeled CPD	HMDB
4-Nitrophenol, copper(1+) salt	HMDB
4-Nitrophenol, potassium salt	HMDB
4-Nitrophenol, tin (2+) salt	HMDB
4-Nitrophenol, 14C-labeled CPD	HMDB
4-Nitrophenol, ammonium salt	HMDB
4-Nitrophenol, ion(1-)	HMDB
4-Nitrophenol, ion(1-) hydride	HMDB
4-Nitrophenol, sodium salt	HMDB
4-Nitrophenol, 2,6-(14)C2-labeled CPD	HMDB
4-Nitrophenol, aluminum salt	HMDB
4-Nitrophenol, cesium salt	HMDB
4-Nitrophenol, iron(3+) salt	HMDB
4-Nitrophenol, lithium salt	HMDB
4-Nitrophenol, manganese salt	HMDB
4-Nitrophenol, zinc salt	HMDB
4-Hydroxy-1-nitrobenzene	HMDB
4-Nitrophenolate	HMDB
4-Nitrophenol	HMDB

Chemical Formula

C₆H₅NO₃

Average Molecular Mass

139.109 g/mol

Monoisotopic Mass

139.027 g/mol

CAS Registry Number

100-02-7

IUPAC Name

4-nitrophenol

Traditional Name

P-nitrophenol

SMILES

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

InChI Identifier

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

InChI Key

BTJIUGUIPKRLHP-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-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:16836 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Intestine
Liver
Placenta
Platelet

Pathways

Not Available

Applications

Not Available

Biological Roles

human xenobiotic metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colorless to light yellow solid.

Experimental Properties

Property	Value
Melting Point	113.8°C
Boiling Point	Not Available
Solubility	11.6 mg/mL at 20°C [SCHWARZENBACH,RP et al.(1988)]

Predicted Properties

Property	Value	Source
Water Solubility	3.6 g/L	ALOGPS
logP	1.93	ALOGPS
logP	1.61	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	7.07	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	34.36 m³·mol⁻¹	ChemAxon
Polarizability	12.22 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
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kr-9200000000-6a367c2627bf30cad163	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00or-9500000000-a23a22fc322241325904	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9400000000-670d24ff2b2b121a7ab8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9400000000-b5aea5436a88b29179e9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05n0-9300000000-f284a324180bf4d7ffc2	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-2009127011-85632179856636169d28	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6t-1900000000-70af7d7902cd35a26f29	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kr-9200000000-6a367c2627bf30cad163	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00or-9500000000-a23a22fc322241325904	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9400000000-670d24ff2b2b121a7ab8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9400000000-b5aea5436a88b29179e9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05n0-9300000000-f284a324180bf4d7ffc2	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-2009127011-85632179856636169d28	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6t-1900000000-70af7d7902cd35a26f29	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kr-9200000000-6a367c2627bf30cad163	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00or-9500000000-a23a22fc322241325904	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9400000000-670d24ff2b2b121a7ab8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9400000000-b5aea5436a88b29179e9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05n0-9300000000-f284a324180bf4d7ffc2	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-2009127011-85632179856636169d28	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6t-1900000000-70af7d7902cd35a26f29	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kr-9200000000-6a367c2627bf30cad163	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00or-9500000000-a23a22fc322241325904	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-7900000000-d4915e2347113b56d32c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9800000000-7bde61a3b7f0a23ddd41	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-00dl-0900000000-653240f82298b3880e70	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-014l-9100000000-1dd6a69ee33aeb4207a3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-014r-9000000000-397a0913b382e58ae418	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-00kr-9200000000-039471e02c3307757a0c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-00or-9500000000-a23a22fc322241325904	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-000i-9400000000-12717928037244536b6b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-000i-9400000000-f133ed564f0a12bd3871	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-05n0-9300000000-d39a8dbf21962717a2ee	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-9200000000-bff0a2a3c15629cc6ec2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-052r-0900000000-1279a141e229fec8dbd4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-052r-0900000000-1279a141e229fec8dbd4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-9200000000-bff0a2a3c15629cc6ec2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00r6-9300000000-5cb2a9e8e318ca2474fd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1900000000-0c7b180f083127156f27	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 - 15V, Negative	splash10-052r-0900000000-7545ed558dcbc5a7a386	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-052r-0900000000-24c57afe8ccf403e589b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4r-2900000000-396ebc9986624989747e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-d01a64d09fb568b883b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-58e0d9a2ff9a60a8c4f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-2900000000-fbf4f5da283a46ec8ed8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-3c17676b62ba6a9be8d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-4dcec4bcef5be284e738	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002r-3900000000-de3f2773a5601a2eec1b	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kr-9300000000-d76f14df8da868057d44	Spectrum
1D NMR	1H 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
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
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (22) ; inhalation (22) ; dermal (22)

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, 21)

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. (22)

Toxicity Values

LD50: 380 mg/kg (Oral, Mouse) (24) LD50: 75 mg/kg (Intraperitoneal, Mouse) (24)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

4-Nitrophenol is used mainly to make fungicides and dyes, and to darken leather. It is also used in the synthesis of drugs such as paracetamol, phenetidine, and acetophenetidine. (22, 23)

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. (22, 21)

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. (21)

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. (21)

Concentrations