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2-Amino-5-nitrophenol
5-NITRO-2-AMINOPHENOL · 2-HYDROXY-4-NITROANILINE · NSC 7087 · CI 76535 · rodolyba · ncic55970 · Sulpho OAVS · ursolyellowbrowna
Identifikatoren & physikalische Daten
| CAS No. | 121-88-0 |
|---|---|
| Summenformel | C6H6N2O3 |
| Durchschnittliche Molmasse | 154,12 g/mol |
| Monoisotopische Masse | 154,03784205 g/mol |
| SMILES | Nc1ccc([N+](=O)[O-])cc1O |
| InChIKey | DOPJTDJKZNWLRB-UHFFFAOYSA-N |
| PubChem CID | 4984721 |
| ChEMBL | CHEMBL164989 |
| ChEBI | CHEBI:82384 |
| EC No. | 204-503-8 |
| DTXSID | DTXSID1020063 |
| Lokaler Name | 2-Amino-5-nitrophenol |
Chemische & physikalische Eigenschaften
| XLogP | 1,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 92,1 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 156 |
| Stoffklassen | Nitrogen Compounds -> Nitrophenols |
| Kosmetika | Cosmetic ingredients (2-Amino-5-Nitrophenol) -> CIR (Cosmetic Ingredient Review) |
| Color/Form | Olive-brown, brown to orange crystalline solidOrange needles when recrystallized from water |
| Löslichkeit | less than 1 mg/mL at 68 °F (NTP, 1992)Slightly soluble in waterSoluble in ethanol, acetone, and benzeneSoluble in deuterated DSMODMSO (Slightly), Methanol (Slightly)insoluble |
| Schmelzpunkt | 388 to 396 °F (decomposes) (NTP, 1992)205.8 °C198-202 °C (dec.) (lit.) |
| Dampfdruck | 0.0000352 [mmHg] |
| Physical Description | 2-amino-5-nitrophenol appears as brown amorphous granules or powder. Melting point 198-202 °C.Olive-brown, brown, or orange solid[HSDB] Green crystalline solid[MSDSonline] |
| Collision Cross Section | 125.3 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID1020063] |
| Siedepunkt | 322.46°C (rough estimate) |
| Dichte | 1.3617 (estimate) |
| Brechungsindex | 1.6890 (rough estimate) |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | 8.08±0.19(Predicted) |
| Farbe | Rust brown to brown |
| BRN | 972974 |
| Henry-Konstante | 1.3×107 mol/(m3Pa) at 25℃, HSDB (2015) |
| Kosmetik-Inhaltsstoffe Funktionen | HAIR DYEING |
| InChI | InChI=1S/C6H6N2O3/c7-5-2-1-4(8(10)11)3-6(5)9/h1-3,9H,7H2 |
| InChIKey | DOPJTDJKZNWLRB-UHFFFAOYSA-N |
| SMILES | C1(O)=CC([N+]([O-])=O)=CC=C1N |
| CAS Datenbank | 121-88-0(CAS DataBase Reference) |
| EPA chemische Informationen | 2-Amino-5-nitrophenol (121-88-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (95%): Causes skin irritation [Warning Skin corrosion/irritation]P203, P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2175 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H317: May cause an allergic skin reaction [Warning Sensitization, Skin] |
|---|---|
| Regulatorische Informationen | Chemical: Phenol, 2-amino-5-nitro-Status: Active Update: 03-08-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/12835 |
| Weitere Sicherheitsinformationen | IMAP assessments - Phenol, 2-amino-5-nitro-: Human health tier II assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. |
| Gefahrenübersicht | A mutagen and tumorigen[RTECS] Causes diarrhea in high-dose feeding studies of rats[HSDB] A skin, eye, mucous membrane, and upper respiratory tract irritant[CAMEO] An irritant[MSDSonline] |
| Reaktive Gruppe | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| Special Reports | DHHS/NTPToxicology & Carcinogenesis Studies of 2-Amino-5-nitrophenol in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 334 (1988) NIH Publication No. 88-2590 |
| Reactivity Profile | 2-AMINO-5-NITROPHENOL is a mild reducing agent. Incompatible with strong oxidizing agents. Reacts slowly with oxygen in the air at room temperature. Stable at temperatures up to 140 °F for two weeks when kept in the dark and under nitrogen. Stable under nitrogen for up to 24 weeks 77 °F. Incompatible with strong bases (NTP, 1992). Incompatible with acid chlorides and acid anhydrides. |
| Air and Water Reactions | Is slowly oxidized by air at room temperature. Insoluble in water. |
| Hazard Classes and Categories | Skin Irrit. 2 (95%)Skin sensitisation - category 1 |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992) |
| 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. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol 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 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated 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 exposure 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, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Personal Protective Equipment (PPE) | MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 85(SRC), determined from a structure estimation method(2), indicates that 2-amino-5-nitrophenol is expected to have high mobility in soil(SRC). Volatilization of 2-amino-5-nitrophenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.8X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2-Amino-5-nitrophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-5 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2007).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 85(SRC), determined from a structure estimation method(2), indicates that 2-amino-5-nitrophenol 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 7.8X10-13 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 an estimated log Kow of 0.99(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(3). Biodegradation data were not available(SRC, 2007).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-amino-5-nitrophenol, which has an estimated vapor pressure of 3.5X10-5 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-amino-5-nitrophenol 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 41 hours(SRC), calculated from its rate constant of 9.4X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-amino-5-nitrophenol may be removed from the air by wet or dry deposition(SRC). |
| 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.org |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=121-88-0] |
| Medical Surveillance | Routine checking of lips, tongue and nail beds of exposed personnel for signs of cyanosis. /Protect/ from exposure those individuals with anemia, cardiovascular or pulmonary diseases. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-amino-5-nitrophenol can be estimated to be 85(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-amino-5-nitrophenol is expected to have high mobility in soil(SRC). |
| Artificial Pollution Sources | 2-Amino-5-nitrophenol's production and use as an intermediate in the manufacture azo dyes, which are used for coloring synthetic resins, lacquers, inks and wood stains and its use as a dye in semi-permanent hair coloring products and limited use in permanent hair coloring products(1) may result in its release to the environment through various waste streams. |
| Carcinogen Classification | 2-Amino-5-nitrophenolGroup 3: Not classifiable as to its carcinogenicity to humansVolume 57: (1993) Occupational Exposures of Hairdressers and Barbers and Personal Use of Hair ColourantsSome Hair Dyes, Cosmetic Colourants, Industrial Dyestuffs and Aromatic Amines1992 |
| Environmental Bioconcentration | An estimated BCF of 3 was calculated in fish for 2-amino-5-nitrophenol(SRC), using an estimated log Kow of 0.99(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for 2-amino-5-nitrophenol is estimated as 7.8X10-13 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-amino-5-nitrophenol is expected to be essentially nonvolatile from water surfaces(2). 2-Amino-5-nitrophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-5 mm Hg(SRC), determined from a fragment constant method(3). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ Male Charles River CD rats (10 per group) received intraperitoneally either 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, or 4-amino-2-nitrophenol in a 10% aqueous DMSO solution. The LD50 for 2-amino-4-nitrophenol was reported to be 246 mg/kg, the LD50 for 2-amino-5-nitrophenol was reported to be greater than 800 mg/kg, and the LD50 for 4-amino-2-nitrophenol was reported to be 302 mg/kg./LABORATORY ANIMALS: Acute Exposure/ 2-Amino-4-nitrophenol, 2-amino-5-nitrophenol, and 4-amino-2-nitrophenol were orally administered to groups of five Charles River CD rats of each sex in an oil-in-water emulsion. The LD50 values for 2-amino-4-nitrophenol and 2-amino-5-nitrophenol were greater than 4000 mg/kg and the LD50 for 4-amino-2-nitrophenol was calculated to be 33 mg/kg./LABORATORY ANIMALS: Acute Exposure/ ... This study tested 33 dyes in guinea pigs using a modified Buehler and Klecak method for open epicutaneous testing. The dyes were tested at an induction concentration of 10% and challenge concentrations of 10.0%, 5.0%, and 2.5%. Nine of the 33 dyes tested /including 2-amino-5-nitrophenol/ produced positive allergic reactions in the guinea pig model ... . When eight of the nine positive dyes were retested using a 1% induction concentration, five dyes /including 2-amino-5-nitrophenol/ produced allergic contact dermatitis at a 1% challenge concentration ... , two at a 0.5% challenge concentration ( /including/ 2-amino-5-nitrophenol ... ), and one at a 0.25% challenge concentration (2-amino-5-nitrophenol). DNCB at a 0.5% induction/challenge concentration was used as a positive control. .../LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... Sixty B6C3F-1 mice were divided into six groups containing five mice/sex/group. The mice received either twelve doses of 2-amino-5-nitrophenol or corn oil (control material) at one of the following doses: 0, 313, 625, 1250, 2500, or 5000 mg/kg over a 16-day period. Clinical observations were performed twice daily, body weights were recorded weekly, and animals were necropsied. Nineteen mice died prior to the end of the study. Two males and five females died in the 5000 mg/kg group, three males and three females died in the 2500 mg/kg group, one female died in the 625 mg/kg group and two vehicle control males died. No significant difference in body weights occurred between treated and control animals and clinical observations were limited to loose stools in the males in the 5000 mg/kg group and two males were prostrate for the first week of the study in the 2500 mg/kg group. The LD50 in mice was greater than 1250 mg/kg but less than 2500 mg/kg.For more Non-Human Toxicity Excerpts (Complete) data for 2-AMINO-5-NITROPHENOL (14 total), please visit the HSDB record page. |
| Populations at Special Risk | Routine checking of lips, tongue and nail beds of exposed personnel for signs of cyanosis. /Protect/ from exposure those individuals with anemia, cardiovascular or pulmonary diseases. |
| Evidence for Carcinogenicity | Evaluation: There is inadequate evidence in humans for the carcinogenicity of 2-amino-5-nitrophenol. There is limited evidence in experimental animals for the carcinogenicity of 2-amino-5-nitrophenol. Overall evaluation: 2-Amino-5-nitrophenol is not classifiable as to its carcinogenicity to humans (Group 3). |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 2811 |
| Zollcode | 29222900 |
| RTECS-Nr. | SJ6302500 |
| R-Sätze (R) | 36/37/38-68-20/21/22 |
| Toxizität | LD50 oral in rat: > 4gm/kg |
| Gefahrensymbole | Xi,Xn |
| Sicherheitshinweise (S) | 26-36/37-45-36/37/39-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 121-88-0(Hazardous Substances Data) |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Verwenden
2-Amino-5-nitrophenol is used in hair dyes and as an intermediate in preparing azo dyes.