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Cupferron

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Name

Cupferron

EINECS 205-183-2
CAS No. 135-20-6 Density 1.3092 (rough estimate)
PSA 55.73000 LogP 2.04840
Solubility <0.1 g/100 mL at 18.5 °C in water Melting Point 150-155 °C (dec.)(lit.)
Formula C6H9N3O2 Boiling Point 243.8 °C at 760 mmHg
Molecular Weight 155.156 Flash Point 101.3 °C
Transport Information UN 2811 6.1/PG 3 Appearance white to light yellow crystalline powder
Safety 26-36/37-45 Risk Codes 25-36/37/38-40-45-43-23/24/25
Molecular Structure Molecular Structure of 135-20-6 (Cupferron) Hazard Symbols ToxicT
Synonyms

Benzenamine,N-hydroxy-N-nitroso-, ammonium salt (9CI);Hydroxylamine, N-nitroso-N-phenyl-,ammonium salt (8CI);Ammonium N-nitroso-N-phenylhydroxylamine;Kupferron;N-Nitroso-N-phenylhydroxyamine ammonium salt;N-Nitroso-N-phenylhydroxyamine-ammonium compd.;N-Nitroso-N-phenylhydroxylamineammonium salt;

Article Data 4

Cupferron Synthetic route

624-91-9

methyl nitrite

100-65-2

N-Phenylhydroxylamine

135-20-6

cupferron

Conditions
ConditionsYield
With diethyl ether; ammonia
100-65-2

N-Phenylhydroxylamine

110-46-3

isopentyl nitrite

135-20-6

cupferron

Conditions
ConditionsYield
With diethyl ether; ammonia
100-65-2

N-Phenylhydroxylamine

135-20-6

cupferron

Conditions
ConditionsYield
With n-Butyl nitrite; ammonia In diethyl ether at 0℃; Yield given;
98-95-3

nitrobenzene

4-ethoxycarbonyl-benzenediazonium-tetrafluoroborate

4-ethoxycarbonyl-benzenediazonium-tetrafluoroborate

135-20-6

cupferron

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH4Cl, Zn, H2O / ethanol / 70 °C
2: NH3, n-butyl nitrite / diethyl ether / 0 °C
View Scheme
135-20-6

cupferron

495-48-7

azoxybenzene

Conditions
ConditionsYield
In ethanol at 78℃; for 2h;85%
In ethanol at 78℃; for 2h; Product distribution; effect of the solvent;85%
67-56-1

methanol

753-73-1

dimethyltin dichloride

135-20-6

cupferron

6957-22-8

4-pyridinealdazine

1606128-91-9

[μ-(1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene){Me2Sn(cupferron)2}2]*MeOH

Conditions
ConditionsYield
Stage #1: methanol; dimethyltin dichloride; 4-pyridinealdazine In ethanol at 20℃; for 0.166667h; Schlenk technique; Inert atmosphere;
Stage #2: cupferron at 20℃; for 1h; Schlenk technique; Inert atmosphere;
82%
753-73-1

dimethyltin dichloride

135-20-6

cupferron

dimethylbis(N-nitroso-N-phenylhydroxylaminato)tin(IV)

Conditions
ConditionsYield
In methanol at 20℃; for 1h;82%
753-73-1

dimethyltin dichloride

135-20-6

cupferron

1135-32-6

trans-1,2-bis(4-pyridyl)ethylene

[μ-(1,2-di(4-pyridyl)ethylene){Me2Sn(N-Nitroso-N-phenylhydroxylamine)2}2]

Conditions
ConditionsYield
Stage #1: dimethyltin dichloride; trans-1,2-bis(4-pyridyl)ethylene In water for 1h;
Stage #2: cupferron In water for 1h;
82%
553-26-4

4,4'-bipyridine

64-17-5

ethanol

753-73-1

dimethyltin dichloride

135-20-6

cupferron

1606128-89-5

[μ-(4,4'-bipyridine){Me2Sn(cupferron)2}2]*EtOH

Conditions
ConditionsYield
Stage #1: 4,4'-bipyridine; ethanol; dimethyltin dichloride at 20℃; for 0.166667h; Schlenk technique; Inert atmosphere;
Stage #2: cupferron In ethanol at 20℃; for 1h; Schlenk technique; Inert atmosphere;
75%

rhodium(III) chloride trihydrate

135-20-6

cupferron

68-12-2, 33513-42-7

N,N-dimethyl-formamide

51025-16-2

[Rh(N-nitroso-N-phenylhydroxylamine)(CO)2]

Conditions
ConditionsYield
Stage #1: rhodium(III) chloride trihydrate; N,N-dimethyl-formamide In water Reflux;
Stage #2: cupferron In water at 20℃;
70%

Cupferron Chemical Properties

Molecular Formula: C6H9N3O2
Molar mass: 155.15 g/mol
EINECS: 205-183-2
Flash Point: 101.3 °C
Boiling Point: 243.8 °C at 760 mmHg
Vapour Pressure: 0.0169 mmHg at 25°C
Melting point: 150-155 °C (dec.)(lit.)
Storage temp: 2-8°C
Water solubility: <0.1 g/100 mL at 18.5 ºC
Appearance: White to light yellow crystalline powder
Product categories: Amines
Structure of Cupferron (135-20-6):
          
XLogP3-AA: 2.7
H-Bond Donor: 1
H-Bond Acceptor: 4
IUPAC Name: Azanium N-oxido-N-phenylnitrous amide
Canonical SMILES: C1=CC=C(C=C1)N(N=O)[O-].[NH4+]
InChI: 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

Cupferron Toxicity Data With Reference

1.    

mmo-sat 100 µg/plate

    ENMUDM    Environmental Mutagenesis. 7 (Suppl 5)(1985),1.
2.    

cyt-grh-orl 1 ppm

    JCGEDO    Journal of Cytology and Genetics. 1 (1966),75.
3.    

eye-rbt 20 mg/24 H MOD

    85JCAE    Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,510.
4.    

orl-rat TDLo:123 g/kg/78 W-C:CAR

    NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-100 ,1978.
5.    

orl-mus TDLo:437 g/kg/78 W-C:CAR

    NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-100 ,1978.
6.    

orl-rat TD:9040 mg/kg/65 W-C:ETA

    ZEKBAI    Zeitschrift fuer Krebsforschung. 69 (1967),103.
7.    

orl-rat LD50:199 mg/kg

    GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 32 (3)(1988),48.
8.    

ipr-rat LDLo:50 mg/kg

    KODAK*    Kodak Company Reports. (343 State St., Rochester, NY 14650)
9.    

ivn-mus LD50:180 mg/kg

    CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#04968 .

Carcinogenicity: Cupferron - California: carcinogen, initial date 1/1/88 NTP: Suspect carcinogen

Cupferron Consensus Reports

NTP 10th Report on Carcinogens. NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-100 ,1978. . Reported in EPA TSCA Inventory. Community Right-To-Know List.

Cupferron Safety Profile

Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Poison by intravenous route. An eye irritant. Solutions with thorium salts are unstable explosives above 15°C. Solutions with titanium or zirconium salts are unstable explosives above 40°C. When heated to decomposition it emits very toxic NH3 and NOx. See also N-NITROSO COMPOUNDS and AMINES.
 

Hazard Codes: T
Risk Statements:
23:  Toxic by inhalation
24:  Toxic in contact with skin
25:  Toxic if swallowed
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin
40:  Limited evidence of a carcinogenic effect
41:  Risk of serious damage to eyes
43:  May cause sensitization by skin contact
45:  May cause cancer
Safety Statements:
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing 
37:  Wear suitable gloves
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
53:  Avoid exposure - obtain special instruction before use

Cupferron Specification

 Cupferron (135-20-6) also can be called Cupferron, ammonium salt ; Ammonium cupferron ; N-Nitroso-N-phenylhydroxylamine; 4benzenamine, N-hydroxy-N-nitroso-, ammonium salt ; Ammonium 2-oxo-1-phenylhydrazinolate .It is hazardous,so the first aid measures and others should be known.Such as: When on the skin: first,should  flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing. Secondly,Get shoesmedical aid . Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.Then get medical aid soon.While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.Notes to physician: Treat supportively and symptomatically.
In addition, Cupferron (135-20-6) is sensitive with air and ight, and absorbs moisture or water from the air, and not be exposured to moist air or water ,and you must not take it with strong acids, strong bases, and incompatible materials.And also prevent it to broken down into hazardous decomposition products: oxides of nitrogen,carbon dioxide,carbon monoxide.

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