135-20-6 Usage
Description
Cupferron, also known as N-Nitroso-N'-phenylhydroxylamine, is a light yellow or cream-colored crystalline compound with a melting point of 163-164°C. It is soluble in water and alcohol and is commonly used as a reagent in various chemical analyses and separations. Cupferron is a white or cream-colored flaky crystal and is classified as a pesticide.
Uses
Used in Chemical Analysis:
Cupferron is used as a quantitative analysis reagent for a wide range of elements, including aluminum, zinc, copper, iron, gallium, mercury, manganese, niobium, tin, tantalum, thorium, titanium, vanadium, and zirconium. It is particularly effective for the determination of copper(II), aluminum(III), bismuth(III), iron(III), mercury(II), thorium(IV), tin(IV), titanium(III), vanadium(IV), and zirconium(IV).
Used in Polymer Industry:
Cupferron serves as a polymerization inhibitor due to its unique characteristics and minimal required amounts. It can be used as an alternative to the widely used phenol polymerization inhibitor BHT.
Used in Colorimetric Determination:
Cupferron is utilized for colorimetric determination of the weight of various elements such as aluminum, bismuth, copper, iron, mercury, zinc, manganese, niobium, gallium, tantalum, thorium, titanium, vanadium, and tin. It is also used for quantitative determination of iron in strong acid solutions, quantitative analysis of vanadates, and separation of copper and iron along with other metals.
Used in Separation of Metals:
Cupferron acts as a reagent for separating tin from zinc and copper and iron from other metals. It quantitatively precipitates iron from strongly acidic solutions and serves as a quantitative reagent for vanadates, forming a dark-red precipitate soluble in alkali solutions, and for titanium, forming a yellow precipitate.
Used in Specific Metal Determination:
Cupferron was initially considered specific for iron(II) and copper(II), but later studies revealed that it forms complexes with several other metals as well. It is now primarily used for the determination of copper(II) and has proven suitable for aluminum(III), bismuth(III), iron(III), mercury(II), thorium(IV), tin(IV), titanium(III), vanadium(IV), and zirconium(IV). The zirconium(IV) complex is the most stable, and cupferron precipitates zirconium(IV) quantitatively from aqueous media containing sulfuric acid.
Used in Metal Ion Separation:
Cupferron enables the separation of various metal ions, such as iron(III) from aluminum(III) and manganese(II), and titanium(IV), zirconium(IV), and hafnium(IV) from other metal ions. The precipitates formed are not of stoichiometric composition and are usually ignited, with the metal oxide residues weighed for analysis.
Used in Determination of Specific Elements:
Cupferron is a reagent for the determination of cerium, copper, iron, tin, and titanium.
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.
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.
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
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
135-20-6Relevant 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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