2-Aminophenol

ORTHO AMINO PHENOL · O-AMINOPHENOL · OAP · Phenol, o-amino- · Orsin · Rodol 2G · 2-amino-pheno · 2-HYDROXYANILINE

Identifikatoren & physikalische Daten

CAS No.	27598-85-2
Summenformel	C6H7NO
Durchschnittliche Molmasse	109,13 g/mol
Monoisotopische Masse	109,05276384 g/mol
SMILES	Nc1ccccc1O
InChIKey	CDAWCLOXVUBKRW-UHFFFAOYSA-N
PubChem CID	5801
ChEMBL	CHEMBL28319
ChEBI	CHEBI:18112
EC No.	202-431-1
DTXSID	DTXSID8024498
Lokaler Name	2-Aminophenol

Chemische & physikalische Eigenschaften

XLogP	0,6
Polarare Oberfläche (TPSA)	46,3
H-Brücken-Donoren	2
H-Brücken-Akzeptoren	2
Frei drehbare Bindungen	0
Schwere Atome	8
Formalladung	0
Komplexität	74,9
Stoffklassen	Nitrogen Compounds -> Amino PhenolsDye
Arzneimittel	Pharmaceuticals -> Listed in ZINC15
Kosmetika	Cosmetic ingredients (o-Aminophenol) -> CIR (Cosmetic Ingredient Review)Hair dyeing
SpringerMaterials Properties	13C nuclear magnetic resonance spectrum
LogP (Verteilungskoeffizient)	log Kow = 0.620.57
Dichte	1.328 (NTP, 1992) - Denser than waterwill sink1.328 g/cu cm at 25 °C1.3 g/cm³
Color/Form	Crystals, rapidly becoming brownWhite orthorhombic bipyramidal needles from benzene or waterWhite crystalsturn brown with ageCOLORLESS RHOMBIC NEEDLES OR PLATES
Löslichkeit	less than 0.1 mg/mL at 70 °F (NTP, 1992)1 g dissolves in 50 mL cold water, 23 mL alcoholSlightly soluble in toluene, chloroform, and cold watersoluble in ethanol, and hot water, very soluble in acetonitrile, ethyl acetate, acetone, dimethyl sulfoxideSoluble in ethyl ethervery soluble in ethanolslightly soluble in benzene, trifluoroacetic acidIn water, 2.0X10+3 mg/L at 20 °C17 g/L (20°C)17 g/L (20 ºC)
Flammpunkt	168 °C (334 °F) - closed cup>175 °C c.c.
Siedepunkt	Sublimes at 307 °F at 11 mmHg (NTP, 1992)Sublimes at 153 °C243 °C @760 [mm Hg]164 °C (11.2515 mmHg)
Decomposition	When heated to decomposition it emits toxic /nitroxides/.170-174 °C
Schmelzpunkt	342 to 343 °F (NTP, 1992)170-174 °CMP: 172-173 °Csublimes on further heating172 °C
Dampfdruck	14 hPa (153 °C)
Brechungsindex	1.5444 (estimate)
Lagerbedingungen	Store below +30°C.
Aggregatzustand	Powder
pKa (Säurekonstante)	4.78, 9.97(at 20℃)
Farbe	White to brown
pH	6.5-7.5 (10g/l, H2O, 20℃)
Merck	14,461
BRN	606075
Henry-Konstante	4.9×104 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität	Stable, but may be air or light sensitive. Incompatible with strong oxidizing agents.
Kosmetik-Inhaltsstoffe Funktionen	HAIR DYEING
InChI	1S/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2
InChIKey	CDAWCLOXVUBKRW-UHFFFAOYSA-N
SMILES	Nc1ccccc1O
LogP (Verteilungskoeffizient)	0.620
CAS Datenbank	95-55-6(CAS DataBase Reference)
NIST chemische Informationen	Phenol, 2-amino-(95-55-6)
EPA chemische Informationen	o-Aminophenol (95-55-6)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P261, P264, P270, P271, P280, P301+P317, P304+P340, P317, P318, P330, P405, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Regulatorische Informationen	Chemical: Phenol, 2-amino-Chemical: Phenol, amino-Status: Active Update: 19-02-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/198562-Aminophenol: Does not have an individual approval but may be used under an appropriate group standard
Weitere Sicherheitsinformationen	IMAP assessments - Phenol, 2-amino-: Human health tier II assessment
DOT-Kennzeichnung	Poison
Brandgefahren	Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Brandpotenzial	Combustible
Gesundheitsgefahren	SYMPTOMS: Symptoms of exposure to this compound include redness of the skin, coughing, and nausea.
Gefahrenübersicht	Skin sensitization is the greatest hazard from industrial exposure. Occupational asthma and methemoglobinemia have been reported after dust inhalation. [HSDB from Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963. 2131] Can induce methemoglobinemiaA skin sensitizer[ICSC]
Reaktive Gruppe	Phenols and Cresols
EG-Einstufung	Symbol: XnR: 20/22-68S: (2)-28-36/37
UN-Einstufung	UN Hazard Class: 6.1UN Pack Group: III
Special Reports	European Commission, ESISIUCLID Dataset, 2-Aminophenol (95-55-6) (2000 CD-ROM edition).[Available from, as of June 7, 2010: http://esis.jrc.ec.europa.eu/]Elder RLJ Am Coll Toxicol 7 (3): 279-334 (1988). Final report on the safety assessment of p-aminophenol, m-aminophenol & o-aminophenol. Review liver, immune system, reproduction, mutagenicity, embryotoxicity, kinetics, methemoglobinemia, renal tubular necrosis, photosensitization, skin irritation, eye irritation, & carcinogenicity of hair dye.
Reactivity Profile	O-AMINOPHENOL can react with oxidizing agents. (NTP, 1992) THF forms explosive products with 2-aminophenol [Lewis 3227].
Brandbekämpfung	This compound is not very flammable but any fire involving this compound may produce dangerous vapors. You should evacuate the area. All firefighters should wear full-body protective clothing and use self-contained breathing apparatuses. You should extinguish any fires involving this chemical with a dry chemical, carbon dioxide, foam, or halon extinguisher. (NTP, 1992)Use alcohol-resistant foam, carbon dioxide, water spray, powder.
Erste-Hilfe-Maßnahmen	Fresh air, rest. Refer for medical attention.Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer for medical attention .
Erste Hilfe	EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Sichere Lagerung	Store in an area without drain or sewer access. Well closed. Separated from oxidants and food and feedstuffs.
Brandbekämpfungsverfahren	Use dry chemical, carbon dioxide, or alcohol foam extinguishers. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or shows any signs of deforming), withdraw immediately to a secure position ... The only respirators recommended for fire fighting are self-contained breathing apparatuses that have full facepieces and are operated in a pressure-demand or other positive-pressure mode. /Anisidines/If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. /Aminophenols/
Lagerbedingungen	Store in tightly closed containers in a cool, well-ventilated area. Aminophenols must be stored to avoid contact with strong oxidizers (such as chlorine, bromine, and fluorine), since violent reactions occur. /Aminophenols/
Reinigungsverfahren	Spill handling: keep dust under control. Use a vacuum or wet method to reduce dust during clean-up. Do not sweep. Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection of your regional office of the federal EPA for specific recommendations. /Aminophenols/
Freisetung ohne Brand	SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Entsorgungsverfahren	SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations.Incineration. /Aminophenols/
Verschüttetes entsorgen	Personal protection: chemical protection suit and particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Preventive Measures	... Disposable natural rubber latex gloves and disposable PVC gloves should not be used repeatedly for handling the hair dye products /p-aminophenol, m-aminophenol, o-aminophenol, and p-phenylenediamine/.If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Aminophenols/Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind ... Avoid bodily contact with the material ... Do not handle broken packages unless wearing appropriate personal protective equipment. /Aminophenols/SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Isolation and Evacuation	Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:
Treatment	Methemoglobinemia can be treated with supplemental oxygen and methylene blue 1% solution administered intravenously slowly over five minutes followed by IV flush with normal saline. Methylene blue restores the iron in hemoglobin to its normal (reduced) oxygen-carrying state. (L1613)
Wechselwirkungen	An investigation was carried out of the effects of ortho-aminophenol (95556) (o-AP), meta-aminophenol (591275) (m-AP), para-aminophenol (123308) (p-AP) & acetaminophen (103902) (AAP) on the induction of preneoplastic lesions in the liver & kidney of male Fischer-344-rats by N-ethyl-N-hydroxyethylnitrosamine (13147256) (EHEN). The rats in this 52 wk investigation included those give 0.1% EHEN in their drinking water for 2 wk & then, beginning 1 wk later, given 0.8% of either o-AP, m-AP, p-AP or AAP in the basal diet for 49 wkthose given EHEN & thereafter only the basal diet& those given one of the test cmpds without prior EHEN admin. Body, liver & kidney weights were determined for sacrificed rats, & liver sections were subjected to immunohistochemical exam of glutathione-S-transferase placental type (GSTP) positive foci. The numbers of GSTP positive foci in the liver were significantly decreased in rats given o-AP, m-AP, p-AP or AAP after EHEN as compared to values for rats given EHEN alone. However, lowered incidences of GSTP positive foci were observed only in rats given o-AP or AAP after EHEN. Only p-AP & AAP gave significantly higher incidences of microadenoma & adenoma in the kidney.
Gesundheitliche Auswirkungen	2-Aminophenol may act as a skin sensitizer and cause contact dermatitis. In addition, inhalation of large amounts can cause methemoglobinemia and bronchial asthma. (T21)
Ökotoxizitätswerte	LD50 Coturnix coturnix japonica (Japanese Quail) oral 316 mg/kg bw endpoint: mortalityLD50 House Sparrow oral 316 mg/kg bwLD50 Redwinged Blackbird oral > 1000 mg/kg bwLD50 Starling oral > 1000 mg/kg bwLC50Species: Danio rerio (zebra danio, eggs)Conditions: freshwater, static, 26 °C, dissolved oxygen >7 mg/LConcentration: 0.033 mg/L (0.033-0.034 mg/L) (33 ug/L (33-34 ug/L)) for 72 hr /formulated product, 99% pure/
Umweltverhalten	TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 90(SRC), determined from a structure estimation method(2), indicates that 2-aminophenol is expected to have high mobility in soil(SRC). However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC). Measured pKa values are 4.72 and 9.71(5), for the amine and hydroxy functional groups, respectively(6)2-aminophenol is amphoteric and behaves either as a weak acid or weak basethe basic character usually predominates(5). Volatilization of 2-aminophenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(7). 2-Aminophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5X10-4 Hg at 25 °C(SRC), determined from a fragment constant method(8). Based on screening tests, 2-aminophenol is expected to biodegradewhen present at 100 mg/L, in a respirometry screening test using an activated sludge inoculum, 45% of the theoretical BOD was reached in 10 days(9). A rate constant of 0.279X10-2 per hour was measured for 2-aminophenol in a screening test using a non-adapted activated sludge inoculum(10). Under denitrifying conditions in sediment, 2-aminophenol was mineralized following a long lag phase at a rate of 12.9 umol/L/day(11). It was not mineralized under methanogenic conditions in a 26-week sediment grab sample study(11).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 90(SRC), determined from a structure estimation method(2), indicates that 2-aminophenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of 0.62(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 2-Aminophenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Based on screening tests, 2-aminophenol is expected to biodegrade when present at 100 mg/L, in a respirometry screening test using an activated sludge inoculum, 45% of the theoretical BOD was reached in 10 days(7). A rate constant of 0.279X10-2 per hour was measured for 2-aminophenol in a screening test using a non-adapted activated sludge inoculum(8). Under denitrifying conditions in sediment, 2-aminophenol was mineralized following a long lag phase at a rate of 12.9 umol/L/day(9). It was not mineralized under methanogenic conditions in a 26-week sediment grab sample study(9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-aminophenol, which has an estimated vapor pressure of 5.0X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2-aminophenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 5 hours(SRC), calculated from its rate constant of 7.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-aminophenol may be removed from the air by wet or dry deposition(SRC). 2-Aminophenol absorbs light at wavelengths 281 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Unerwünschte Wirkungen	Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect
Expositionspfade	The substance can be absorbed into the body by ingestion, through the skin and by inhalation of its aerosol.Oral (L138)inhalation (L138)
Toxizitätsübersicht	Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org2-Aminophenol interacts with both adult and fetal hemoglobin, forming methemoglobin. In comparison to its isomers, 3-aminophenol and 4-aminophenol, 2-aminophenol is the most effective in forming methemoglobin. Since methemoglobin cannot bind oxygen like hemoglobin can, elevated levels of methemoglobin cause a condition called methemoglobinemia, which can result in tissue hypoxia. (L1613, A2862)
Ökotoxizitätsauszüge	/BIRDS and MAMMALS/ Ip injection of 50 mg/kg /of 2-Aminophenol/ in Japanese quail produced a peak of 25% methemoglobin in the blood after 10 min.
Signs and Symptoms	See Ingestion.MAY BE ABSORBED!Redness.Blue lips, fingernails and skin. Confusion. Convulsions. Cough. Dizziness. Headache. Laboured breathing. Nausea. Unconsciousness. Symptoms may be delayed.2-Aminophenol may cause contact dermatitis. Signs and symptoms of methemoglobinemia may include shortness of breath, cyanosis, mental status changes, headache, fatigue, exercise intolerance, dizziness and loss of consciousness. Severe methemoglobinemia can result in dysrhythmias, seizures, coma, and death. (T21, L1613)
ICSC Environmental Data	This substance may be hazardous to the environment. Special attention should be given to aquatic organisms.
Soil Adsorption/Mobility	Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-aminophenol can be estimated to be 90(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-aminophenol is expected to have high mobility in soil. However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3-4), suggesting that mobility may be much lower in some soils(SRC). Measured pKa values are 4.72 and 9.71(5), for the amine and hydroxy functional groups, respectively(6)2-aminophenol is amphoteric and behaves either as a weak acid or weak basethe basic character usually predominates(5). At pH 8.4, 25.5% of added 2-aminophenol is sorbed by an organoclay(7). The sorptive capacity of clays for amine-substituted phenolic sorbate decreased with increasing pH above the corresponding pKa(8).
F	8-10-23
Wassergefährdungsklasse (WGK)	2
TSCA-Inventar-Status	TSCA listed
UN-Transportnummer	UN 2512 (AMINOPHENOLS (o-, m-, p-))
Zollcode	29222900
RTECS-Nr.	SJ4950000
R-Sätze (R)	20/22-68-34-20/21/22
Toxizität	LD50 orally in Rabbit: 1300 mg/kg
Gefahrensymbole	Xn,C
Sicherheitshinweise (S)	28-36/37-28A-45-36/37/39-26-68-20/22
Gefahrenklasse	6.1Acute Tox. 4 InhalationAcute Tox. 4 OralMuta. 2
Verpackungsgruppe	III
Lagerklasse	6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Gefahrstoffdaten	95-55-6(Hazardous Substances Data)
Selbstentzündungstemperatur	190 °C

Anwendungen & Verwendung

Verwenden

2-Aminophenol is an isomer of 4-Aminophenol and is used as a reagent for the synthesis of heterocyclic compounds and dyes. It is also used to make dyes and pharmaceuticals.

Herstellung & Synthese

synthetische

2-Aminophenol is obtained by reduction of o-nitrophenol with sodium sulfide or hydrogen gas.