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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 | Hazard Symbols | T | |
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 |
Conditions | Yield |
---|---|
With diethyl ether; ammonia |
Conditions | Yield |
---|---|
With diethyl ether; ammonia |
Conditions | Yield |
---|---|
With n-Butyl nitrite; ammonia In diethyl ether at 0℃; Yield given; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NH4Cl, Zn, H2O / ethanol / 70 °C 2: NH3, n-butyl nitrite / diethyl ether / 0 °C View Scheme |
Conditions | Yield |
---|---|
In ethanol at 78℃; for 2h; | 85% |
In ethanol at 78℃; for 2h; Product distribution; effect of the solvent; | 85% |
methanol
dimethyltin dichloride
cupferron
4-pyridinealdazine
[μ-(1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene){Me2Sn(cupferron)2}2]*MeOH
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 1h; | 82% |
Conditions | Yield |
---|---|
Stage #1: dimethyltin dichloride; trans-1,2-bis(4-pyridyl)ethylene In water for 1h; Stage #2: cupferron In water for 1h; | 82% |
4,4'-bipyridine
ethanol
dimethyltin dichloride
cupferron
[μ-(4,4'-bipyridine){Me2Sn(cupferron)2}2]*EtOH
Conditions | Yield |
---|---|
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% |
cupferron
N,N-dimethyl-formamide
[Rh(N-nitroso-N-phenylhydroxylamine)(CO)2]
Conditions | Yield |
---|---|
Stage #1: rhodium(III) chloride trihydrate; N,N-dimethyl-formamide In water Reflux; Stage #2: cupferron In water at 20℃; | 70% |
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
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
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.
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 (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.