N-Phenylhydroxylamine

109.12588

109.13

202-875-6

282MU82Z9A

223099

2811

DTXSID3025889

NEEDLES FROM SATURATED SODIUM CHLORIDE SOLN|NEEDLES FROM WATER, BENZENE OR PETROLEUM ETHER SOLN

2928000090

32.3

1.56070

N-phenylhydroxylamine appears as tan to brown crystals. (NTP, 1992)

1.1143 (rough estimate)

82 °C

204.59°C (rough estimate)

120.2ºC

1.5444 (estimate)

VERY SOL IN CHLOROFORM; INSOL IN PETROLEUM ETHER; FREELY SOL IN ALCOHOL, CARBON DISULFIDE, DIL MINERAL ACID, ETHER, HOT BENZENE, ACETIC ACID

-20°C

0.085mmHg at 25°C

Soluble in hot water.

Alcohols and Polyols

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.

Ⅲ

6.1

UN 2811

3

25

45

NC4900000

T

Unstable - deteriorates with storage. Incompatible with strong oxidizing agents.

P301 + P310

H301

Flash point data for this chemical are not available but it is probably nonflammable. (NTP, 1992)

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

Fires involving this chemical should be controlled with a dry chemical, carbon dioxide, foam or halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store it in a freezer. (NTP, 1992)

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. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

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.

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.

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).

PHENYLHYDROXYLAMINE IS BIOSYNTHESIZED FROM ANILINE & N-ETHYLANILINE IN PIG & RABBIT: HEINZE E, HLAVICA P, KIESE M & LIPOWSKY G; BIOCHEM PHARMAC 19: 641 (1970). HLAVICA P, KIESE M; BIOCHEM PHARMAC 18: 1501 (1969) /FROM TABLE/|PHENYLHYDROXYLAMINE IS METABOLIZED TO ANILINE IN PIG: KADLUBAR FF, MCKEE EM, ZIEGLER DM; ARCHS BIOCHEM BIOPHYS 156: 46 (1973) /FROM TABLE/|CYTOCHROME P-450 COMPLEX WAS FORMED BY DIRECT INTERACTION OF NITROSOBENZENE WITH NADPH-REDUCED RAT LIVER MICROSOMES IN ANAEROBIC CONDITIONS, AND BY REACTION OF PHENYLHYDROXYLAMINE WITH AEROBIC MICROSOMES.|DETOXIFICATION BY REARRANGEMENT OF THE PHENYLHYDROXYLAMINE TO ORTHO- AND PARA-AMINOPHENOLS OF LOWER POTENTIAL FOR EXCRETION THROUGH THE KIDNEYS PROBABLY IS RESPONSIBLE FOR RESTORATION OF THE OXYGEN TRANSPORT BALANCE /FOLLOWING CYANOSIS/.|For more Metabolism/Metabolites (Complete) data for N-PHENYLHYDROXYLAMINE (7 total), please visit the HSDB record page.|N-Hydroxyaniline is a known human metabolite of aniline.

...INTRAERYTHROCYTIC RECYCLING ACCOUNTS FOR THE HIGH POTENCY /AS METHEMOGLOBIN FORMER/ OF PHENYLHYDROXYLAMINE RELATIVE TO OTHER COMPOUNDS. ...PHENYLHYDROXYLAMINE & HEMOGLOBIN REACT TO FORM METHEMOGLOBIN & NITROSOBENZENE. IN INTACT NORMAL RED CELL PROVIDED WITH SUBSTRATE, MECHANISMS EXIST FOR REDUCTION OF NITROSOBENZENE TO REGENERATE PHENYLHYDROXYLAMINE.|UNDER ANAEROBIC CONDITIONS, PHENYLHYDROXYLAMINE REACTS WITH THE MODEL NUCLEOPHILE BISULFITE TO FORM ANILINE, O-AMINOPHENOL, 0-AMINOBENZENESULFONIC ACID, AND P-AMINOBENZENESULFONIC ACID. ALL PRODUCTS RESULT FROM IMTERMEDIATES FORMED FROM NUCLEOPHILIC ATTACK OF BOTH BISULFITE AND SULFITE ON THE ARYLHYDROXYLAMINE WITH SUBSEQUENT COVALENT ADDITION-ELIMINATION PROCESSES LEADING TO PRODUCTS. THIS SCHEME IS A POSSIBLE ALTERNATIVE PATHWAY FOR DESCRIBING THE MECHANISM FOR CARCINOGENIC ARYLATION OF NUCLEIC ACID RESIDUES BY ARYLHYDROXYLAMINES NOT REQUIRING THE INTERMEDIACY OF SHORT-LIVED FREE RADICALS OR NITRENIUM IONS.|THE MECHANISM OF SULFHEMOGLOBIN FORMATION AND SPECIES DIFFERENCES IN THE FORMATION OF SULFHEMOGLOBIN AND METHEMOGLOBIN WERE INVESTIGATED. ERYTHROCYTES OR HEMOLYZATES WERE INCUBATED WITH PHENYLHYDROXYLAMINE, ANILINE-HCL OR ITS MONOCHLORO DERIVATIVES IN THE PRESENCE OR ABSENCE OF LIVER MICROSOMES FROM MICE, RATS, GUINEA PIGS, RABBITS, CATS, DOGS, AND MONKEYS. SULFHEMOGLOBIN WAS NOT INDUCED VIA METHEMOGLOBIN. SPECIES DIFFERENCES IN THE PRODUCTION RATES OF N-HYDROXY METABOLITES FROM ANILINE AND ITS DERIVATIVES BY LIVER MICROSOMES (AS WELL AS THE SUSCEPTIBILITY OF ERYTHROCYTES TO N-HYDROXY COMPOUNDS) IN VITRO WERE NOT REFLECTED IN SPECIES DIFFERENCES IN METHEMOBGLOBIN AND SULFHEMOGLOBIN FORMATION IN VIVO.

SYMPTOMS: This compound may cause irritation on contact with skin or mucous me. ACUTE/CHRONIC HAZARDS: This chemical is toxic and has hazardous decomposition products;it is an irritant. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

.../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 SEVERE; WEAKNESS, 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.

hydroxylaminobenzene

ESSENTIALLY 100% AS CHEMICAL INTERMEDIATE

Benzenamine, N-hydroxy-: INACTIVE

A METHOD IS GIVEN FOR DETERMINATION OF ANILINE AND ITS DEGRADATION PRODUCTS IN TISSUES BY HPLC. THE DETECTION LIMIT FOR ANILINE ALONE IS 5 MUMOL/L AND ITS RETENTION VOLUME IS 13.0 ML, WITH ITS METABOLITES (INCLUDING N-PHENYLHYDROXYLAMINE) HAVING THE SAME VALUES. THIS METHOD IS WELL-SUITED FOR MONITORING IN AQUEOUS SOLUTION, ALSO.