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135-20-6 Usage

Analysis reagents

Cupferron is an important analytical reagent, as Ammonium salt of N-nitroso hydroxylamine, commonly known as cupferron. It is usually white or light yellow bright flake scrystal, with sweet odour, long home to darken due to slow decomposition, but in fact can also be used in the analysis. It is soluble in water, benzene, alcohol, ether. The reagent is thermally decomposed to prepare nitrobenzene. Unstable in light and air, we need to save itin a brown reagent grinding mouth bottle, usually place a small amount of ammonium carbonate in bottle packaged with paper or cloth good as a preservative, store in a sealed dark cool place. It can be used as a precipitating agent and solvent extraction agent of copper, iron, tin, titanium, vanadium, chromium and other elements, as a masking agent for the determination of rare earth. Nitrobenzene is reduced with zinc powder in an aqueous solution of ammonium chloride to get phenylhydroxylamine, which is then dissolved in ether, lead to excessive ammonia, and addn-butyl nitrite, then get cupferron, can form a stable five-membered ring chelate with metal ions, therefore, it is common organic precipitant. It can quantitatively measure Fe3 + ions in the acid solution, can also be measure Cu2 +, Sn4 +, Ti4 +, Ga3 +, Hf4 +and other ions, and vanadate (VO-3, VO3-3). When Fe3 +, Cu2 + ions mixedwith other metal ions together, the reagent can be used to separate them out. It is a chelating extractant for Al3 +, Au3 +, Be2 +, Co2 +, La3 +, Pu4 + and other ions, a masking agent for rare earth metal ions. The above information is edited by the lookchem of Yan Yanyong.

Purification method

Ddd 30g powdered crude into 120ml60 ℃ water, make it all dissolved, add 2g of powdered activated carbon and stir for 10~15min, filtrate with the calcined Buchner, and cool the filtrate to 10~15 ℃, then cool to 0 ℃ overnight. Suction filtration by using a glass filter to precipitate crystals, wash with 10ml ethanol and then wash with 10ml of ether, and dry in air. Cupferron can also be recrystallized with ethanol to purify.

Chemical properties

It is white or cream colored flaky crystals. Melting point is 163-164 ℃, it is soluble in water and alcohol.

Uses

Different sources of media describe the Uses of 135-20-6 differently. You can refer to the following data:
1. 1. Cupferron is used for quantitative analysis for aluminum, zinc, copper, iron, gallium, mercury, manganese, niobium, tin, tantalum, thorium, titanium, vanadium, zirconium and other elements 2. It is used as polymerization inhibitor, due to unique polymerization inhibition characteristics of cupferron, also the amount is small, can be used as an alternative of phenol polymerization inhibitor BHT, which is current largely applicated. 3. Cupferron is used for colorimetric determination for the weight of aluminum, bismuth, copper, iron, mercury, zinc, manganese, niobium, gallium, tantalum, thorium, titanium, vanadium, tin and other elements of. It is used for quantitative determination of iron in the strong acid solution, quantitative analysis of vanadate, separation of copper and iron together with the other metals, as a masking agent for measuring rare earths.
2. As a reagent for separating Sn from Zn, and Cu and Fe from other metals. Ppts iron quantitatively from strongly acid solution; as a quantitative reagent for vanadates with which it gives a dark-red ppt soluble in alkali solution, and for Ti with which it forms a yellow ppt; also suitable for the colorimetric estimation of Al.
3. The 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.
4. Cupferron is a reagent for determination of Ce, Cu, Fe, Sn, and Ti.

Production method

Benzene hydroxylamine ether solution was cooled in an ice bath, lead to an excess of ammonia, while stirring and continue adding the ammonia, solution of n-butyl nitrite was added for about 1h, then stir for 15min. Filter precipitate of cupferron, wash with diethyl ether, dry to get products. The product should be stored in a brown glass bottle, the bottle is placed a small amount of ammonium carbonate wrapped by paper (or cloth) as a stabilizer.

Category

Pesticide

Toxicity grading

highly toxic

Acute toxicity

oral-rat LD 50: 199 mg/kg, intravenous-Mouse LD50: 180 mg/kg

Irritation data

Eye-rabbit 20 mg/24 hours moderate

Explosive hazardous properties

Explosive with thorium salt, zirconium salt or titanium salt solution at room temperature

Flammability hazard characteristics

It produces toxic fumes of nitrogen oxides and ammonia at high temperature.

Storage characteristics

Treasury ventilation, low-temperature drying

Extinguishing agent

Dry powder, foam, sand, carbon dioxide, water mist

Chemical Properties

Different sources of media describe the Chemical Properties of 135-20-6 differently. You can refer to the following data:
1. white to light yellow crystalline powder
2. Cupferron is a creamy-white crystalline compound

General Description

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

Air & Water Reactions

Hygroscopic. Soluble in water.

Reactivity Profile

Cupferron 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.

Fire Hazard

Flash point data for Cupferron are not available; however, Cupferron is probably combustible.

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℃. When heated to decomposition it emits very toxic NH3 and NOx. See also N-NITROSO COMPOUNDS and AMINES

Potential Exposure

Cupferron is used to separate tin from zinc, and copper and iron from other metals in the laboratory. Cupferron also finds application as a quantitative reagent for vanadates and titanium; and for the colorimetric determination of aluminum. The potential for exposure appears to be greatest for those engaged in analytical or research studies involving use of the chemical. Workers may also be exposed to the compound during manufacturing processes.

Carcinogenicity

Cupferron is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Recrystallise it twice from EtOH after treatment with Norite and finally once with EtOH. The crystals are washed with diethyl ether and air dried, then stored in the dark over solid ammonium carbonate. A standard solution (ca 0.05M prepared in air-free H2O) is prepared daily from this material for analytical work and is essentially 100% pure. [Olsen & Elving Anal Chem 26 1747 1954.] It can also be washed with Et2O, dried and stored as stated. In a sealed, dark container it can be stored for at least 12 months without deterioration. 260nm (CHCl3). max [Marvel Org Synth Coll Vol I 177 1941, Elving & Olson J Am Chem Soc 78 4206 1956, Beilstein 16 IV 891.] Possible CARCINOGEN.

Incompatibilities

Forms unstable and possibly explosive compounds with thorium salts; titanium, zirconium.

Check Digit Verification of cas no

The CAS Registry Mumber 135-20-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 5 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 135-20:
(5*1)+(4*3)+(3*5)+(2*2)+(1*0)=36
36 % 10 = 6
So 135-20-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H6N2O2.H3N/c9-7-8(10)6-4-2-1-3-5-6;/h1-5,10H;1H3/p+1

135-20-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A16551)  Cupferron, 97+%   

  • 135-20-6

  • 25g

  • 264.0CNY

  • Detail
  • Alfa Aesar

  • (36625)  Cupferron, 97% min   

  • 135-20-6

  • 100g

  • 994.0CNY

  • Detail
  • Aldrich

  • (675636)  Cupferron  97%, reagent grade

  • 135-20-6

  • 675636-100G

  • 2,628.99CNY

  • Detail
  • Aldrich

  • (675636)  Cupferron  97%, reagent grade

  • 135-20-6

  • 675636-500G

  • 8,646.30CNY

  • Detail

135-20-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Cupferron

1.2 Other means of identification

Product number -
Other names COPPERONE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:135-20-6 SDS

135-20-6Synthetic 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

135-20-6Related news

Application of Voltammetric Method of Total Chromium Determination in the Presence of Cupferron (cas 135-20-6) for Selective Determination of Cr(VI) in Water Samples09/30/2019

A voltammetric method of Cr(VI) determination in a flow system based on the combination of selective accumulation of the product of Cr(VI) reduction on hanging mercury drop electrode and a very sensitive method of chromium determination in the presence of cupferron previously described is propos...detailed

Direct Determination of Cadmium Traces in Natural Water by Adsorptive Stripping Voltammetry in the Presence of Cupferron (cas 135-20-6) as a Chelating Agent09/29/2019

A sensitive, simple and fast adsorptive stripping voltammetric procedure for trace determination of cadmium in natural samples containing high concentrations of surface active substances and humic substances has been developed. The method is based on adsorptive accumulation of the Cd(II)‐cupfer...detailed

135-20-6Relevant articles and documents

Synthesis, anti-microbial, toxicity and molecular docking studies of N-nitroso-N-phenylhydroxylamine (cupferron) and its derivatives

Isa, Mustafa A.,Muller, Alfred,Sonopo, Molahlehi,Waziri, Ibrahim,Williams, D. Bradley G.

, (2021/10/06)

Bacterial resistance to antimicrobial agents is increasing at an alarming rate globally and requires new lead compounds for antibiotics. In this study, N-phenyl-N-nitroso hydroxylamine (cupferron) and its derivatives have been synthesised using readily available starting materials. The compounds were obtained in high yield and purity. They show activity towards a range of Gram-positive and Gram-negative pathogenic bacteria, with minimum inhibitory concentration (MIC) values as low as 2 μg.mL?1 against the tested organisms, especially for Gram-positive species. Toxicity studies on the lead compound 3b indicate insignificant effects on healthy cell lines. Molecular docking studies on the lead compound identify possible binding modes of the compound, and the results obtained correlate with those of in vitro and MIC studies. The lead compound shows excellent drug-likeness properties.

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