Product Name

  • Name

    Cupferron

  • EINECS 205-183-2
  • CAS No. 135-20-6
  • Article Data4
  • CAS DataBase
  • Density 1.3092 (rough estimate)
  • 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;
  • PSA 55.73000
  • LogP 2.04840

Synthetic route

methyl nitrite
624-91-9

methyl nitrite

N-Phenylhydroxylamine
100-65-2

N-Phenylhydroxylamine

cupferron
135-20-6

cupferron

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

N-Phenylhydroxylamine

isopentyl nitrite
110-46-3

isopentyl nitrite

cupferron
135-20-6

cupferron

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

N-Phenylhydroxylamine

cupferron
135-20-6

cupferron

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

nitrobenzene

4-ethoxycarbonyl-benzenediazonium-tetrafluoroborate

4-ethoxycarbonyl-benzenediazonium-tetrafluoroborate

cupferron
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
cupferron
135-20-6

cupferron

azoxybenzene
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%
methanol
67-56-1

methanol

dimethyltin dichloride
753-73-1

dimethyltin dichloride

cupferron
135-20-6

cupferron

4-pyridinealdazine
6957-22-8

4-pyridinealdazine

[μ-(1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene){Me2Sn(cupferron)2}2]*MeOH
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%
dimethyltin dichloride
753-73-1

dimethyltin dichloride

cupferron
135-20-6

cupferron

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

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

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

dimethyltin dichloride

cupferron
135-20-6

cupferron

trans-1,2-bis(4-pyridyl)ethylene
1135-32-6

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

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

[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%
4,4'-bipyridine
553-26-4

4,4'-bipyridine

ethanol
64-17-5

ethanol

dimethyltin dichloride
753-73-1

dimethyltin dichloride

cupferron
135-20-6

cupferron

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

rhodium(III) chloride trihydrate

cupferron
135-20-6

cupferron

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

[Rh(N-nitroso-N-phenylhydroxylamine)(CO)2]
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
135-20-6

cupferron

sodium N-nitroso-N-phenylhydroxylaminate
36598-71-7

sodium N-nitroso-N-phenylhydroxylaminate

Conditions
ConditionsYield
With sodium cation exchange resin In ethanol66%
cupferron
135-20-6

cupferron

methyl iodide
74-88-4

methyl iodide

(Z)-2-methoxy-1-phenyldiazene 1-oxide
25370-94-9, 121058-44-4

(Z)-2-methoxy-1-phenyldiazene 1-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide Alkylation;55%
cupferron
135-20-6

cupferron

ethyl iodide
75-03-6

ethyl iodide

N-ethoxy-N'-phenyldiimide N'-oxide

N-ethoxy-N'-phenyldiimide N'-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide Alkylation;49%
cupferron
135-20-6

cupferron

2-nitrophenylmethyl bromide
3958-60-9

2-nitrophenylmethyl bromide

N-(o-nitrobenzyloxy)-N'-phenyldiimide N'-oxide

N-(o-nitrobenzyloxy)-N'-phenyldiimide N'-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide Alkylation;44%
benzyl bromide
100-39-0

benzyl bromide

cupferron
135-20-6

cupferron

N-(benzyloxy)-N'-phenyldiimide N'-oxide

N-(benzyloxy)-N'-phenyldiimide N'-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide Alkylation;41%
cupferron
135-20-6

cupferron

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

N-(p-nitrobenzyloxy)-N'-phenyldiimide N'-oxide

N-(p-nitrobenzyloxy)-N'-phenyldiimide N'-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide Alkylation;41%
cupferron
135-20-6

cupferron

1-iodo-propane
107-08-4

1-iodo-propane

N-n-propoxy-N'-phenyldiimide N'-oxide

N-n-propoxy-N'-phenyldiimide N'-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide Alkylation;40%
cupferron
135-20-6

cupferron

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

N-(p-methoxybenzyloxy)-N'-phenyldiimide N'-oxide

N-(p-methoxybenzyloxy)-N'-phenyldiimide N'-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide Alkylation;36%
bromethyl methyl ether
13057-17-5

bromethyl methyl ether

cupferron
135-20-6

cupferron

N-((methoxymethyl)oxy)-N'-phenyldiimide N'-oxide

N-((methoxymethyl)oxy)-N'-phenyldiimide N'-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide Alkylation;35%
cupferron
135-20-6

cupferron

allyl bromide
106-95-6

allyl bromide

N-(allyloxy)-N'-phenyldiimide N'-oxide

N-(allyloxy)-N'-phenyldiimide N'-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide Alkylation;31%
cupferron
135-20-6

cupferron

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

N-(3-hydroxypropoxy)-N'-phenyldiimide N'-oxide

N-(3-hydroxypropoxy)-N'-phenyldiimide N'-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide Alkylation;23%
phenylthiomethyl chloride
7205-91-6

phenylthiomethyl chloride

cupferron
135-20-6

cupferron

N-(phenylthiomethyloxy)-N'-phenyldiimide N'-oxide

N-(phenylthiomethyloxy)-N'-phenyldiimide N'-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide Alkylation;17%
chloro-methylsulfanyl-methane
2373-51-5

chloro-methylsulfanyl-methane

cupferron
135-20-6

cupferron

N-(methylthiomethyloxy)-N'-phenyldiimide N'-oxide
291308-93-5

N-(methylthiomethyloxy)-N'-phenyldiimide N'-oxide

Conditions
ConditionsYield
With potassium iodide In N,N-dimethyl-formamide Alkylation;16%
cupferron
135-20-6

cupferron

1,2-dibromomethane
74-95-3

1,2-dibromomethane

di(phenyl-NON-azoxy)formal

di(phenyl-NON-azoxy)formal

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 72h;4.4%
pyridine
110-86-1

pyridine

methyl magnesium iodide
917-64-6

methyl magnesium iodide

cupferron
135-20-6

cupferron

methane
34557-54-5

methane

cupferron
135-20-6

cupferron

potassium phenylnitrosohydroxylaminate

potassium phenylnitrosohydroxylaminate

Conditions
ConditionsYield
With hydrogenchloride; potassium hydroxide; ammonium hydroxide 1) 5-10 deg C, 1.5 h; Yield given. Multistep reaction;
cupferron
135-20-6

cupferron

1,3-Dichloropropane
142-28-9

1,3-Dichloropropane

1,9-diphenyl-1,2,8,9-tetraaza-3,7-dioxanona-1,8-diene 1,9-dioxide

1,9-diphenyl-1,2,8,9-tetraaza-3,7-dioxanona-1,8-diene 1,9-dioxide

Conditions
ConditionsYield
With tetramethyl ammoniumhydroxide 2) MeCN, reflux, 5 h; Yield given. Multistep reaction;
cupferron
135-20-6

cupferron

allyl 7β-((2-thien-2-yl)acetamido)-3-(iodomethyl)-3-cephem-4-carboxylate
129393-69-7

allyl 7β-((2-thien-2-yl)acetamido)-3-(iodomethyl)-3-cephem-4-carboxylate

A

C23H22N4O6S2

C23H22N4O6S2

B

(6R,7R)-3-[N-(4-Nitro-phenyl)aminooxymethyl]-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester

(6R,7R)-3-[N-(4-Nitro-phenyl)aminooxymethyl]-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide
cupferron
135-20-6

cupferron

Conditions
ConditionsYield
With phosphate buffer; ethylenediaminetetraacetic acid In water; acetonitrile at 25℃; pH=7.0; Decomposition;
cupferron
135-20-6

cupferron

N-(chloromethyloxy)-N'-phenyldiimide N'-oxide

N-(chloromethyloxy)-N'-phenyldiimide N'-oxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 16 percent / potassium iodide / dimethylformamide
2: sulfuryl chloride / CH2Cl2 / 0 - 20 °C
View Scheme

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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