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Phenylhydroxylamin
Phenylhydroxylamine · NCI C-60093 · N-HYDROXYANILINE · N-HYDROXYLANILINE · Hydroxyaminobenzene · N-Phenylhydroxyamine · N-Hydroxybenzenamine · N-Phenylhydroxylamin
Identifikatoren & physikalische Daten
| CAS No. | 100-65-2 |
|---|---|
| Summenformel | C6H7NO |
| Durchschnittliche Molmasse | 109,13 g/mol |
| Monoisotopische Masse | 109,05276384 g/mol |
| SMILES | ONc1ccccc1 |
| InChIKey | CKRZKMFTZCFYGB-UHFFFAOYSA-N |
| PubChem CID | 7518 |
| ChEMBL | CHEMBL320474 |
| ChEBI | CHEBI:28902 |
| EC No. | 202-875-6 |
| DTXSID | DTXSID3025889 |
| Lokaler Name | Phenylhydroxylamin |
Chemische & physikalische Eigenschaften
| XLogP | 0,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 32,3 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 59,5 |
| Stoffklassen | Nitrogen Compounds -> Hydroxylamines |
| Color/Form | NEEDLES FROM SATURATED SODIUM CHLORIDE SOLNNEEDLES FROM WATER, BENZENE OR PETROLEUM ETHER SOLN |
| Löslichkeit | Soluble in hot water (NTP, 1992)VERY SOL IN CHLOROFORMINSOL IN PETROLEUM ETHERFREELY SOL IN ALCOHOL, CARBON DISULFIDE, DIL MINERAL ACID, ETHER, HOT BENZENE, ACETIC ACID20g/L(5 ºC) |
| Schmelzpunkt | 181 to 183 °F (NTP, 1992)82 °C80-84℃ |
| Dampfdruck | 0.00795 [mmHg] |
| Physical Description | N-phenylhydroxylamine appears as tan to brown crystals. (NTP, 1992)Solid[Merck Index] Tan to brown solid[CAMEO] |
| Stability/Shelf Life | DETERIORATES ON STORAGE |
| Siedepunkt | 204.59°C (rough estimate) |
| Dichte | 1.1143 (rough estimate) |
| Brechungsindex | 1.5444 (estimate) |
| Lagerbedingungen | -20°C |
| pKa (Säurekonstante) | 9.00±0.70(Predicted) |
| Aggregatzustand | solid |
| Farbe | Light brown |
| Stabilität | Unstable - deteriorates with storage. Incompatible with strong oxidizing agents. |
| InChI | 1S/C6H7NO/c8-7-6-4-2-1-3-5-6/h1-5,7-8H |
| InChIKey | CKRZKMFTZCFYGB-UHFFFAOYSA-N |
| SMILES | ONc1ccccc1 |
| EPA chemische Informationen | Phenylhydroxylamine (100-65-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (97.6%): Toxic if swallowed [Danger Acute toxicity, oral]P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory. |
|---|---|
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Flash point data for this chemical are not available but it is probably nonflammable. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: This compound may cause irritation on contact with skin or mucous me. |
| Gefahrenübersicht | Occupational cases of severe poisoning have been reportedMarkedly increases sister chromatid exchange in cultured human fibroblastsCauses methemoglobinemia in rats and miceLethal-dosed rats did not exhibit methemoglobin levels sufficiently high to cause death by anoxia, suggesting that methemoglobinemia is not responsible for acute toxicityEmergency treatment: Methemoglobinemia[HSDB] An irritant[CAMEO] Irritating to human skinCauses hematuria and methemoglobinemia in subcutaneous, lethal-dose studies of rats and rabbitsRepeated dose studies of rats produce weight loss and changes to blood[RTECS] May cause irritation[Aldrich MSDS] |
| Reaktive Gruppe | Alcohols and Polyols |
| Reactivity Profile | N-PHENYLHYDROXYLAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. |
| Air and Water Reactions | Soluble in hot water. |
| Hazard Classes and Categories | Acute Tox. 3 (97.6%) |
| Brandbekämpfung | Fires involving this chemical should be controlled with a dry chemical, carbon dioxide, foam or halon extinguisher. (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, 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. |
| 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. |
| Wechselwirkungen | NORHARMAN WAS COMUTAGENIC WITH PHENYLHYDROXYLAMINE WHEN TESTED WITH SALMONELLA TYPHIMURIUM TA98 IN THE PRESENCE OF S-9 MIX. THE COMUTAGENIC EFFECTS WERE FOUND ONLY WITH THE FRAMESHIFT-TYPE MUTANTS OF S TYPHIMURIUM. |
| Unerwünschte Wirkungen | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as primary toxic effect. |
| Effluent Concentrations | AGMENELLUM QUADRUPLICATUM STRAIN PR-6 AND OSCILLATORIA SP STRAIN JCM WERE GROWN PHOTOAUTOTROPHICALLY IN THE PRESENCE OF ANILINE. CYANOBACTERIUM WAS EXTREMELY SENSITIVE TO THE ANILINE DERIVATIVE PHENYLHYDROXYLAMINE. ANILINE AND DERIVATIVES HAVE BEEN FOUND IN THE EFFLUENT FROM DYE MANUFACTURING PLANTS. |
| Human Toxicity Excerpts | .../THERE HAVE BEEN/ RATHER SEVERE POISONINGS FROM PHENYLHYDROXYLAMINE /IN INDUSTRIAL PLANTS/, & STILL HAVE NOT OBSERVED IN MAN CONCN BEYOND APPROX 75% METHEMOGLOBIN.METHEMOGLOBIN LEVELS TO 40% MAY EXIST WITHOUT SYMPTOMS OTHER THAN SENSE OF WELL-BEING. @ HIGHER CONCN HEADACHE MAY BECOME SEVEREWEAKNESS, ATAXIA & LIGHTHEADEDNESS OCCUR. WITH INCREASING CONCN...DYSPNEA, TACHYCARDIA & ALARMING CYANOSIS ARE NOTED. EVEN @...LEVELS APPROXIMATING 75%, HOWEVER, RECOVERY WITHOUT SPECIFIC THERAPY HAS BEEN THE RULE. /AROMATIC AMINO COMPD/HUMAN FIBROBLASTS WERE ALLOWED TO ATTACH TO PLASTIC PETRI DISHES FOR 4 HOURS AND EXPOSED IN SERUM-FREE MEDIUM FOR 2 HOURS TO N-PHENYLHYDROXYLAMINE (0.001-0.5 MMOL). THE TREATMENT MEDIUM WAS REPLACED WITH COMPLETE MEDIUM CONTAINING 5-BROMODEOXYURIDINE (10 MUMOL), AND CELLS WERE ALLOWED TO GROW FOR 48 HOURS WITH COLCEMIDE PRESENT FOR THE FINAL 4.5 HOURS. CELL CYCLE ANALYSES (PERCENTAGE OF CELLS IN 1ST, 2ND, OR 3RD DIVISION) REVEALED THAT N-PHENYLHYDROXYLAMINE INHIBITED CELL PROLIFERATION. CELL DEATH WAS SEEN AT DOSES OF 0.5 MMOL. SIGNIFICANT INCREASES IN SISTER CHROMATID EXCHANGE WERE FOUND. N-PHENYLHYDROXYLAMINE INDUCED A DOSE-RELATED INCREASE IN SISTER CHROMATID EXCHANGE FREQUENCY WITH A 1.4-FOLD ELEVATION. |
| Artificial Pollution Sources | THE NONENZYMATIC REDUCTION OF NITROSOBENZENE BY NADPH AND NADH IN AQUEOUS BUFFER SOLUTION AT 25 °C IS DESCRIBED. BOTH REACTANTS QUANTITATIVELY CONVERT NITROSOBENZENE TO PHENYLHYDROXYLAMINE. THE OXIDATION OF PHENYLHYDROXYLAMINE BY NAD(P) TO NITROSOBENZENE IS ONLY STIMULATED BY A FACTOR OF 1.2 OVER OXIDATION IN ITS ABSENCE (WHEN THE RATIO OF NADP:PHENYLHYDROXYLAMINE WAS 8:1). |
| Non-Human Toxicity Excerpts | ...RATS /DIED WHEN DOSED WITH/...BETA-PHENYLHYDROXYLAMINE...BUT LEVELS OF METHEMOGLOBIN WERE INSUFFICIENT TO CAUSE DEATH BY ANOXIA. .../IT WAS/ CONCLUDED THAT METHEMOGLOBINEMIA PLAYS NO IMPORTANT PART IN ACUTE TOXICITY OF /THIS COMPD/...AS TESTED IN MICE, PHENYLHYDROXYLAMINE, N-HYDROXY-P-AMINOTOLUENE & N-HYDROXY-P-ACETOPHENONE WERE ALL ABOUT EQUIPOTENT, IE GENERATED EQUIVALENT PEAK CONCENTRATIONS OF METHEMOGLOBIN AT EQUAL DOSES. AT SAME TIME THEY WERE 10 OR MORE TIMES MORE POTENT THAN NITRITE, HYDROXYLAMINE, OR SIMPLE AMINOPHENOLS.AROMATIC NITRO AND AMINO COMPOUNDS PROBABLY ARE NOT, IN THEMSELVES, CYANOSIS PRODUCERS, BUT BIOCHEMICAL REDOX PROCESSES CREATE DERIVATIVES WHICH HINDER OXYGEN TRANSPORT TO TISSUES BY FORMING HB-COMPLEXES. ENZYME SYSTEMS CATALYZE OXIDATION OF AMINE GROUP...TO KNOWN CYANOPATHIC NITROSO-...DERIVATIVES. PHENYLHYDROXYLAMINES ARE PROBABLY MOST POTENT CYANOSIS PRODUCERS IN REDOX SERIES. /AROMATIC NITRO AND AMINO COMPOUNDS/A MECHANISM IS PROPOSED IN WHICH CYCLIC CONVERSION OF PHNO TO PHENYLHYDROXYLAMINE WITHIN ERYTHROCYTE LEADS TO ACCUM OF H2O2 WHICH REACTS WITH FERRO-HB, INITIATING OXIDATIVE DEGRADATION OF HEME.For more Non-Human Toxicity Excerpts (Complete) data for N-PHENYLHYDROXYLAMINE (6 total), please visit the HSDB record page. |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2811 |
| Zollcode | 2928009090 |
| RTECS-Nr. | NC4900000 |
| R-Sätze (R) | 25 |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 45 |
| Gefahrenklasse | 6.1Acute Tox. 3 Oral |
| Verpackungsgruppe | Ⅲ |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 100-65-2(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Manufacture of cupferron.
Herstellung & Synthese
synthetische
To a dispersion of 180 gm (2.75 gm-atom) of zinc dust in 500 ml of 50% aqueous ethanol, with vigorous stirring, is added 130 ml (156 gm, 1.27 mole) of nitrobenzene. The reaction is initiated by the dropwise addition of an aqueous ammonium chloride solution and can thereafter be maintained at a controllable rate by the cautious addition of the remaining ammonium chloride solution. The reaction temperature rises during this reduction step. Once reflux has subsided, the basic zinc salts are filtered off using a sintered glass funnel. The light green filtrate is cooled in an ice-salt mixture to precipitate the product. The yield is 100 gm (72.2%), m.p. 81°C. The reduction of 2-methyl-2-nitropropane is carried out in a similar manner at 10-20°C to afford a 68% yield of N-t-butylhydroxylamine (m.p. 60-62°C).