CID 2724103

Base Information

• Chemical Name: CID 2724103
• CAS No.: 135-20-6
• Molecular Formula: C6H9N3O2
• Molecular Weight: 155.156
• Hs Code.: 29299090
• European Community (EC) Number: 205-183-2
• Wikipedia: Cupferron
• Wikidata: Q3007584
• NCI Thesaurus Code: C44362
• Mol file: 135-20-6.mol

Synonyms:cupferron;hydrogen cupferron;N-nitroso-N-phenylhydroxylamine;N-nitroso-N-phenylhydroxylamine ammonium salt

Chemical Property of CID 2724103

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Vapor Pressure: 0.0169mmHg at 25°C
• Melting Point: 150-155 °C (dec.)(lit.)
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 243.8 °C at 760 mmHg
• Flash Point: 101.3 °C
• PSA: 55.73000
• Density: 1.3092 (rough estimate)
• LogP: 2.04840
• Storage Temp.: 2-8°C
• Solubility.: well soluble in water and ethanol.
• Water Solubility.: <0.1 g/100 mL at 18.5℃
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 155.069476538
• Heavy Atom Count: 11
• Complexity: 112

Purity/Quality:

99% ^*data from raw suppliers

Cupferron ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36/37/38-40-45-43-23/24/25
• Safety Statements: 26-36/37-45-53

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC=C(C=C1)N(N=O)[O-].[NH4+]
• Uses: 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. 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. 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. 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.

Technology Process of CID 2724103

There total 5 articles about CID 2724103 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-Phenylhydroxylamine (100-65-2) → cupferron (135-20-6)

Guidance literature:

With n-Butyl nitrite; ammonia; In diethyl ether; at 0 ℃; Yield given;

DOI:10.1080/00304949809355306

Reference yield:

nitrobenzene (98-95-3,26969-40-4) → cupferron (135-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium chloride; zinc / methanol; water / 2.5 h / Heating

2: ammonia; n-Butyl nitrite / diethyl ether / 0.25 h / -10 - 0 °C

With n-Butyl nitrite; ammonia; ammonium chloride; zinc; In methanol; diethyl ether; water;

DOI:10.1016/j.bmcl.2021.128381

Reference yield:

nitrobenzene (98-95-3,26969-40-4) → cupferron (135-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₄Cl, Zn, H₂O / ethanol / 70 °C

2: NH₃, n-butyl nitrite / diethyl ether / 0 °C

With n-Butyl nitrite; ammonia; water; ammonium chloride; zinc; In diethyl ether; ethanol;

DOI:10.1080/00304949809355306

upstream raw materials:

methyl nitrite

N-Phenylhydroxylamine

isopentyl nitrite

nitrobenzene

Downstream raw materials:

azoxybenzene

sodium N-nitroso-N-phenylhydroxylaminate

trans-azoxybenzene