1.0 2009-08-10 21:31:10 UTC 2026-08-23 11:50:05 UTC T3D3579 2-Nitrophenol SmallMolecule 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. Industrial/Workplace Toxin Pollutant Synthetic Toxin Organic Compound Industrial Precursor/Intermediate Aromatic Hydrocarbon Nitrite Pollutant Industrial/Workplace Toxin Synthetic Compound PMT 2-(hydroxy(oxido)amino)phenol 2-Hydroxynitrobenzene 2-nitrophenol ammonium salt O-hydroxynitrobenzene O-nitrofenol O-nitrophenol O-Nitrophenol O-nitrophenol (molten) Ortho-nitrophenol C6H5NO3 139.1088 139.026943031 2-nitrophenol o-nitrophenol 88-75-5 OC1=CC=CC=C1[N+]([O-])=O InChI=1S/C6H5NO3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H IQUPABOKLQSFBK-UHFFFAOYSA-N Organic compounds Benzenoids Phenols Nitrophenols Nitrophenols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Hydrocarbon derivatives Nitroaromatic compounds Nitrobenzenes Organic oxides Organic oxoazanium compounds Organonitrogen compounds Organooxygen compounds Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Allyl-type 1,3-dipolar organic compound Aromatic homomonocyclic compound C-nitro compound Hydrocarbon derivative Monocyclic benzene moiety Nitroaromatic compound Nitrobenzene Nitrophenol Organic 1,3-dipolar compound Organic nitro compound Organic nitrogen compound Organic oxide Organic oxoazanium Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound Aromatic homomonocyclic compounds mononitrophenol Detected and Not Quantified Exogenous Cytoplasm Extracellular Solid Light yellow solid. melting_point 44.8°C solubility 2.5 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)] logp 1.8 logp 1.91 ALOGPS logs -1.52 ALOGPS solubility 4.25e+00 g/l ALOGPS logp 1.61 ChemAxon pka_strongest_acidic 6.43 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac 2-nitrophenol ChemAxon average_mass 139.1088 ChemAxon mono_mass 139.026943031 ChemAxon smiles OC1=CC=CC=C1[N+]([O-])=O ChemAxon formula C6H5NO3 ChemAxon inchi InChI=1S/C6H5NO3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H ChemAxon inchikey IQUPABOKLQSFBK-UHFFFAOYSA-N ChemAxon polar_surface_area 66.05 ChemAxon refractivity 35.36 ChemAxon polarizability 12.08 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Oral (L1661) ; inhalation (L1661) ; dermal (L1661) ; eye contact (L1661). 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. (A2450, L1613) 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. (L1661) LD50: 334 mg/kg (Oral, Rat) (T14) LD50: 378 mg/kg (Intraperitoneal, Mouse) (T14) LD50: 100 mg/kg (Intravenous, Dog) (T14) No indication of carcinogenicity to humans (not listed by IARC). 2-Nitrophenol is used mainly to make dyes, paint coloring, rubber chemicals, and substances that kill molds. (L1661) #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f726c4b8ad0> 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. (L1613) 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. (L1613) 6947 CHEMBL14205 13837787 C01988 16260 CPD-10489 2-Nitrophenol 1745 18203719 11370739 Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Methemoglobinemia ATSDR - Agency for Toxic Substances and Disease Registry (1992). Toxicological profile for nitrophenols. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA).: http://www.atsdr.cdc.gov/toxprofiles/tp50.html BE0000130 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. (A2450, L1613) Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Methemoglobinemia BE0000629 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. (A2450, L1613) Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Methemoglobinemia BE0004987 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. (A2450, L1613) Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Methemoglobinemia BE0004975 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. (A2450, L1613) Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Methemoglobinemia BE0004556 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. (A2450, L1613) Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Methemoglobinemia BE0004998 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. (A2450, L1613) Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Methemoglobinemia BE0004986 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. (A2450, L1613) Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Methemoglobinemia BE0005028 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. (A2450, L1613) Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Methemoglobinemia BE0005021 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. (A2450, L1613) Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. : http://en.wikipedia.org/wiki/Methemoglobinemia BE0000123 AC50 0.01 uM ACEA_T47D_80hr_Positive ACEA Biosciences