1-(4-Nitrophenyl)piperazine

Base Information

• Chemical Name: 1-(4-Nitrophenyl)piperazine
• CAS No.: 6269-89-2
• Molecular Formula: C10H13N3O2
• Molecular Weight: 207.232
• Hs Code.: 29335990
• European Community (EC) Number: 228-443-7
• NSC Number: 33874
• UNII: SE8XST987K
• DSSTox Substance ID: DTXSID40978310
• Nikkaji Number: J211.501H
• Wikidata: Q72495670
• ChEMBL ID: CHEMBL165012
• Mol file: 6269-89-2.mol

Synonyms:1-(4-nitrophenyl)piperazine

Chemical Property of 1-(4-Nitrophenyl)piperazine

Chemical Property:

• Appearance/Colour: yellow to ochre powder
• Vapor Pressure: 2.38E-06mmHg at 25°C
• Melting Point: 131-133 °C(lit.)
• Refractive Index: 1.4830 (estimate)
• Boiling Point: 391.9 °C at 760 mmHg
• PKA: 8.68±0.10(Predicted)
• Flash Point: 190.8 °C
• PSA: 61.09000
• Density: 1.222 g/cm³
• LogP: 1.92140
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 207.100776666
• Heavy Atom Count: 15
• Complexity: 215

Purity/Quality:

99% ^*data from raw suppliers

1-(4-Nitrophenyl)piperazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-24/25-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1)C2=CC=C(C=C2)[N+](=O)[O-]
• Uses: 1-(4-Nitrophenyl)piperazine is a useful synthetic intermediate in the synthesis of Itraconazole (I937500); an orally active antimycotic structurally related to Ketoconazole. Also antifungal.

Technology Process of 1-(4-Nitrophenyl)piperazine

There total 12 articles about 1-(4-Nitrophenyl)piperazine 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: 99.0%

tert-butyl 4-(4-nitrophenyl)piperazine-1-carboxylate (182618-86-6) → 1-(4-Nitrophenyl)piperazine (6269-89-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 24h; Cooling with ice;

DOI:10.3390/ph14111109

Reference yield: 98.0%

piperazine (110-85-0) + para-nitrophenyl bromide (586-78-7) → 1-(4-Nitrophenyl)piperazine (6269-89-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In dimethyl sulfoxide; at 120 ℃; for 12h;

DOI:10.1016/S0040-4039(99)01103-X

Reference yield: 95.0%

piperazine (110-85-0) + 4-Fluoronitrobenzene (350-46-9,178603-76-4) → 1-(4-Nitrophenyl)piperazine (6269-89-2)

Guidance literature:

In N,N-dimethyl-formamide; under 6000.6 Torr;

DOI:10.1039/c5ra09426g

upstream raw materials:

piperazine

4-chlorobenzonitrile

bis(2-bromoethyl)amine hydrobromide

4-nitro-aniline

Downstream raw materials:

1-(4-nitro-phenyl)-4-(toluene-4-sulfonylmethyl)-piperazine

formylamino-[4-(4-nitro-phenyl)-piperazinomethyl]-malonic acid dimethyl ester

1-benzenesulfonylmethyl-4-(4-nitro-phenyl)-piperazine

2,2,2-trifluoro-1-[4-(4-nitro-phenyl)-piperazin-1-yl]-ethanone