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N-Nitroso-N-phenylhydroxylamin,Ammoniumsalz

Cupferron

HCID 2724103
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Grundinformationen

CAS
135-20-6
Standard-SMILES
O=NN([O-])c1ccccc1.[NH4+]
InChIKey
GDEBSAWXIHEMNF-UHFFFAOYSA-O
Summenformel
C6H6N2O2.H3N
Durchschnittliche Molmasse
155,15 g/mol
Monoisotopische Masse
155,06947654

Überblick

Cupferron can cause cancer according to an independent committee of scientific and health experts.

Namen und Bezeichner

Bevorzugter Name
Cupferron
IUPAC
azanium N-oxido-N-phenylnitrous amide
Lokaler Name
N-Nitroso-N-phenylhydroxylamin,Ammoniumsalz
Englischer Name
Cupferron
Summenformel
C6H9N3O2
Molmasse
155.15

Namen und Synonyme

CUPFERRONAmmonium-N-nitrosophenylhydroxylamine135-20-6CupferonKupferonAmmonium cupferronAmmonium nitroso-beta-phenylhydroxylamineCupferron, ammonium saltN-Nitrosophenylhydroxylamine ammonium saltN-Nitroso-N-phenylhydroxylamine ammonium saltN-Nitrosofenylhydroxylamin amonnyN-Nitrosophenylhydroxylamin ammonium salz
Weitere Namen anzeigen
N-NitrosophenylhydroxylamineNPHAKupferronCUPFERRON,REAGENT,ACSN-NITROSO-N-PHENYLHYDROXYLAMINEtongtie
DTXCID90352NCI-C03258Ammonium N-nitrosophenylhydroxylamineNSC-112124N-Nitroso-N-phenylhydroxyamine ammonium saltN-Hydroxy-N-nitroso-benzenamine, ammonium saltHydroxylamine, N-nitroso-N-phenyl-, ammonium saltRefChem:579547

Datenbank-Bezeichner

CAS
135-20-6
PubChem CID

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
56,7 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
1
Schwere Atome
11
Formalladung
0
Komplexität
112

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Nitrogen Compounds -> Other Aromatics (Nitrogen)

Carcinogens

Color/Form · 2 Einträge

Crystals

Creamy-white crystals

Solubility · 4 Einträge

less than 1 mg/mL at 65.3 °F (NTP, 1992)

Freely soluble in water

Freely soluble in alcohol

Slightly soluble in DMSO

DecompositionWhen heated to decomposition it emits toxic fumes of /ammonia and nitrogen oxides/.
Melting Point · 2 Einträge

325 to 327 °F (NTP, 1992)

163.5 °C

Vapor Pressure · 2 Einträge

Negligible (NTP, 1992)

0.0000629 [mmHg]

Physical Description · 2 Einträge

Cupferron appears as light yellow or cream-colored crystals or a brown crystalline solid. As a reagent in the separation of copper and iron.

Creamy-white solid; [HSDB] Light yellow, cream-colored, or brown solid; Hygroscopic; [CAMEO] Pale yellow, odorless crystalline solid; [Alfa Aesar MSDS]

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H301 (98%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 50 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H350: May cause cancer [Danger Carcinogenicity]

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Benzenamine, N-hydroxy-N-nitroso-, ammonium salt

Hazard Traits - Carcinogenicity

Cupferron: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Benzenamine, N-hydroxy-N-nitroso-, ammonium salt: Environment tier I assessment
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 Eintrag

SYMPTOMS: Symptoms of exposure to this compound may include irritation and dermatitis. Methemoglobinemia and eye burns may also occur. Other symptoms may include drowsiness, skin irritation, eye irritation, nausea vomiting, weakness, somnolence, liver damage and unconsciousness.

Hazards Summary · 1 Eintrag

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

O-Alkylation of N-nitroso-N-phenylhydroxylamine ammonium salt (cupferron) was studied for the synthesis of novel nitric oxide (NO) releasing agents. The alkylation occurred regioselectively at the terminal oxygen, leading to a single product N-(alkyloxy)-N'-phenyldiimide N'-oxide as indicated by NMR and X-ray analysis. The O-alkyl derivatives exhibited significantly improved stability compared to their parent compound, cupferron. It was demonstrated that the cupferron O-alkyl derivatives could function as photoreleasing NO donor compounds. N-(N"-acetylphenylalanylmethylenyloxy)-N'-phenyldiimide N'-oxide), which linked the cupferron portion with an amino acid via an acetal moiety, was synthesized as an model NO prodrug where controlled NO release would occur either by increasing pH or by a protease-catalyzed hydrolysis.

Verwendung und Herstellung

Uses · 3 Einträge

Used as an analytical reagent for separation and precipitation of metals and a quantitative reagent for vanadates, titanium, and colorimetric estimation of aluminum; [HSDB]

As a reagent for separating Sn from Zn, and Cu from Fe from other metals. Precipitates iron quantitatively from strongly acid solution; as a quantitative reagent for vanadates with which it gives a dark-rep precipitate solution in alkali solution, for Ti with which it form as a yellow precipitate; also suitable for the coloration estimation of Al.

Reagent chemical ... manufactured to high and well-defined standards of purity

U.S. Production · 2 Einträge

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4817]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical:Benzenamine, N-hydroxy-N-nitroso-,ammonium salt. Aggregated National Production Volume: < 500,000 pounds.

Methods of Manufacturing · 3 Einträge

By treating an ether solution of beta-phenylhydroxylamine with dry ammonia gas and amyl nitrite.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
2724103
DTXSID
DTXSID1020352
ChEMBL
CHEMBL388471
EC Number
205-183-2

Physikochemische Eigenschaften

Schmelzpunkt
150 · 150-155 °C (dec.) (lit.)
Siedepunkt
278.95 °C · 278.95°C (rough estimate)
Dichte
1.3092 · 1.3092 (rough estimate)
Brechungsindex
1.65 · 1.6500 (estimate)
storage temp.
2 · 2-8°C
Löslichkeit
well soluble in water and ethanol.
Aggregatzustand
Powder
Farbe
Needles from water
Wasserlöslichkeit
0.1 g/100 · <0.1 g/100 mL at 18.5 ºC
Merck
14 · 14,2622
BRN
3919107 · 3919107
Stabilität
Stable, but may be moisture sensitive. Incompatible with strong oxidizing agents, strong bases, strong acids.
InChI
1S/C6H5N2O2.H3N/c9-7-8(10)6-4-2-1-3-5-6;/h1-5H;1H3/q-1;/p+1
InChIKey
GDEBSAWXIHEMNF-UHFFFAOYSA-O
SMILES
[H][N+]([H])([H])[H].[O-]N(N=O)c1ccccc1
CAS Datenbank
135 · 135-20-6(CAS DataBase Reference)
NIST chemische Informationen
Cupferron(135-20-6)
EPA chemische Informationen
Cupferron (135-20-6)

Emergency treatment: Methemoglobinemia; [HSDB] Causes various cancers when administered in the diet of rats; [NTP] A skin and eye irritant; May cause methemoglobinemia and liver damage; [CAMEO] A moderate eye irritant; Causes muscle weakness and dyspnea in oral lethal-dose studies of rats; [RTECS] A skin and serious eye irritant; Toxic if swallowed; Suspected carcinogen; [Aldrich MSDS] See 2021 (Volume 127) monograph at IARC.

Reactive GroupAzo, Diazo, Azido, Hydrazine, and Azide Compounds
Special Reports · 2 Einträge

U.S. Department of Health & Human Services/National Toxicology Program; Twelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Cupferron (135-20-6) is listed as reasonably anticipated to be a human carcinogen. First listed in the Third Annual Report on Carcinogens (1983).[Available from, as of March 1, 2012: http://ntp.niehs.nih.gov/?objectid=03C9AF75-E1BF-FF40-DBA9EC0928DF8B15]

DHEW/NCI; Bioassay of Cupferron for Possible Carcinogenicity (1978) Technical Rpt Series No. 100 DHEW Pub No. (NIH) 78-1350

Reactivity ProfileCUPFERRON may be sensitive to prolonged exposure to air. Incompatible with strong oxidizing agents, strong acids and strong bases. Forms unstable solutions with thorium, titanium and zirconium salts. (NTP, 1992)
Air and Water ReactionsHygroscopic. Soluble in water.
Hazard Classes and Categories · 5 Einträge

Acute Tox. 3 (98%)

Carcinogenicity - Category 1B

Carcinogenicity - Category 1B

Acute toxicity (Oral) - Category 3

Carcinogens

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
First Aid · 1 Eintrag

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.

Storage ConditionsKeep in well closed containers to which a piece of ammonium carbonate is added.
Nonfire Spill Response · 1 Eintrag

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.

Disposal Methods · 1 Eintrag

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 quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Protective Action Criteria (PAC) · 3 Einträge

0.60 [mg/m3]

6.6 [mg/m3]

39 [mg/m3]

Personal Protective Equipment (PPE) · 1 Eintrag

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)

Toxikologische Informationen

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Ongoing Test Status · 1 Eintrag

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.[Available at http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=135-20-6]

Carcinogen Classification · 6 Einträge

Cupferron

Group 2B: Possibly carcinogenic to humans

Volume 127: (2021) Some Aromatic Amines and Related Compounds

2021 online

2020

Cupferron

Non-Human Toxicity Excerpts · 1 Eintrag

/OTHER TOXICITY INFORMATION/ Cupferron has a fungicidal and fungistatic effect on cells of the yeast Saccharomyces cerevisiae. At relatively low concn over a short period of time it induces the formation of large numbers of petite (respiratory deficient) mutants. ...

Evidence for CarcinogenicityCupferron: reasonably anticipated to be a human carcinogen.
Probable Routes of Human Exposure · 2 Einträge

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of cupferron is 1 to 99; the data may be greatly underestimated(1).

Mainly through ingestion or inhalation of dry salt. Skin absorption is a secondary route of exposure.

Antidote and Emergency Treatment · 3 Einträge

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic bases/Amines and related compounds/

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/

National Toxicology Program Studies · 1 Eintrag

A bioassay of cupferron for possible carcinogenicity was conducted using Fischer 344 rats and B6C3F1 mice. Cupferron was administered in the feed, at either of two concentrations, to groups of 49 or 50 male and 50 female animals of each species. The time-weighted average high and low dietary concentrations of cupferron were, respectively, 0.30 and 0.15 percent for male and female rats, and 0.4 and 0.2 percent for male and female mice. After a 78 week period of compound administration, observation of the rats continued for an additional period of up to 28 weeks and observation of the mice continued for an additional period of up to 18 weeks. For each species, 50 animals of each sex were placed on test as controls and fed only the basal diet. Among both sexes of rats and mice there was a significant positive association between the dose of cupferron administered and mortality. There were significant positive associations between the concentrations of cupferron admininstered to male and female rats and the incidences of squamous cell carcinomas of the forestomach, hepatocellular carcinomas and neoplastic nodules, and hemangiosarcomas. When a binomial distribution and a spontaneous incidence rate corresponding to the appropriate historical control incidence were assumed, the incidences of auditory sebaceous gland neoplasms in female rats and female mice were significant. There were significant positive associations between the concentrations administered and the incidences of hepatocellular carcinomas in female mice, the incidences of hemangiosarcomas in both sexes of mice, and the incidence of Harderian gland adenomas in both sexes of mice.

RAIS Toxicity Values · 4 Einträge

6.3e-05

CALEPA

0.22

CALEPA

Non-Human Toxicity Values · 2 Einträge

LD50 Mouse iv 180 mg/kg

LD50 Rat oral 199 mg/kg

Hazard Quotient Level 0.1 or Cancer Risk Level 1E-06 · 6 Einträge

2.50e+00

1.00e+01

4.50e-02

1.90e-01

3.50e-01

1.30e+03

Hazard Quotient Level 3 or Cancer Risk Level 1E-04 · 6 Einträge

2.50e+02

1.00e+03

4.50e+00

1.90e+01

3.50e+01

1.30e+03

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 2811 6.1/PG 3
hs_code
29299090
RTECS-Nr.
NC4725000
risk_code
25-36/37/38-40-45-43-23/24/25
Toxizität
TDLo orl-rat: 123 g/kg/78W-C:CAR NCITR* NCI-CGTR-100,78
hazard_code
T
safety_code
26-36/37-45-53
hazard_class
6.1
packing_group
III
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Giftige Stoffe Daten
135-20-6(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 OralCarc. 1BEye Irrit. 2Muta. 2STOT SE 3

REACTION OF PHENYLHYDROXYLAMINE WITH SODIUM NITRITE IN THE PRESENCE OF HYDROCHLORIC ACID, FOLLOWED BY TREATMENT WITH AMMONIA; TREATMENT OF PHENYLHYDROXYLAMINE WITH BUTYL OR AMYL NITRITE AND AMMONIA

Prepared from phenylhydroxylamine by treating with NaNO2 at 0 °C in presence of HCl, filtering, dissolving in ether and treating with NH3, or by treating an ether solution of phenylhydroxylamine with butyl or amyl nitrite and NH3 in the cold.

General Manufacturing InformationBenzenamine, N-hydroxy-N-nitroso-, ammonium salt (1:1): ACTIVE
Anwendungen · 1 Eintrag

VerwendenThe reagent used to be considered as specific for iron(II) and copper(II). However, in the course of later analytical studies it turned out that cupferron forms complexes with several other metals too, even in acidic medium. It is used today primarily for the determination of copper(II), but it has proved suitable for the determination of aluminium(III), bismuth(III), iron(III), mercury(II), thorium(IV), tin(IV), titanium(III), vanadium(IV) and zirconium(IV) as well. Of these, the zirconium(IV) complex is the most stable. Cupferron precipitates zirconium(IV) quantitatively from aqueous media containing sulfuric acid. The reagent gives a precipitate with most of the above metal ions even in strong mineral acidic medium. Only the aluminium(III) complex does not precipitate in the presence of mineral acids. By means of cupferron many metal ions can be separated: thus, for instance, iron(III) can be separated from aluminium(III) and manganese(II) and titanium (IV), zirconium(IV) and hafnium(IV) from many other metal ions, etc. Though the reagent makes possible several separations, the precipitates are not exactly of stoichiometric composition (they almost always contain some excess of the ligand). Hence instead of being directly weighed, the precipitates are usually ignited and the metal oxide residues weighed.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

ButylnitritPhenylhydroxylaminDiammoniumcarbonat

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