BENZO(A)PHENAZINE

Base Information

• Chemical Name: BENZO(A)PHENAZINE
• CAS No.: 225-61-6
• Molecular Formula: C16H10 N2
• Molecular Weight: 230.269
• Hs Code.: 2933990090
• Mol file: 225-61-6.mol

Synonyms:1,2-Benzophenazine;7,12-Diazabenz[a]anthracene; NSC 15305

Chemical Property of BENZO(A)PHENAZINE

Chemical Property:

• Vapor Pressure: 4.34E-08mmHg at 25°C
• Melting Point: 142.5°C
• Refractive Index: 1.5635 (estimate)
• Boiling Point: 456.6°Cat760mmHg
• Flash Point: 208.8°C
• PSA: 25.78000
• Density: 1.291g/cm³
• LogP: 3.93620

Purity/Quality:

99% ^*data from raw suppliers

BENZO(A)PHENAZINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Benzo(a)phenazine is a heterocyclic compound with notable biological properties, including antibiotic, antimalarial, antiparasitic, and antitumor activities. It can be efficiently synthesized via a micelle-catalyzed, regio- and chemoselective one-pot reaction in water, using 2,3-dichloro-1,4-naphthoquinone and o-phenylenediamine as key reactants, highlighting its potential as a pharmacologically relevant scaffold.

Technology Process of BENZO(A)PHENAZINE

There total 3 articles about BENZO(A)PHENAZINE 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: 22.0%

[1-(2-aminophenyl)naphthalen-2-yl]amine (93013-27-5) → Naphtho<2.1-c>cinnolin (195-31-3) + 1,2-benzophenazine (225-61-6)

Guidance literature:

With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; In methanol; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c4cc04911j

Reference yield:

1,2-diamino-benzene (95-54-5) + 1-Nitroso-2-naphthol (131-91-9) → 2,3-diaminephenazine (655-86-7) + 1,2-benzophenazine (225-61-6)

Guidance literature:

With hydrogenchloride; acetic acid;

Reference yield:

nitrobenzene (98-95-3,26969-40-4) + naphthalen-2-ylamine (91-59-8) → 1,2-benzophenazine (225-61-6) + benzo[a]phenazine 12-oxide (18636-87-8)

Guidance literature:

With sodium hydroxide; at 115 - 140 ℃;

upstream raw materials:

nitrobenzene

naphthalen-2-ylamine

1,2-diamino-benzene

1-Nitroso-2-naphthol

Downstream raw materials:

Benzo -phenazin-7-oxid

benzo[a]phenazine-5,6-dione

11H-Indeno[1,2-b]quinoxaline-11-one

16-(3,4-dimethoxyphenyl)-3,3-dimethyl-2,3,4,16-tetrahydro-1H-benzo[a]chromeno[2,3-c]phenazin-1-one

Refernces

Micelles catalyzed one pot regio- and chemoselective synthesis of benzo[a]phenazines and naphtho[2,3-d]imidazoles 'in H₂O'

10.1016/j.tetlet.2014.09.103

The study presents an efficient and environmentally friendly one-pot synthesis method for benzo[a]phenazines and naphtho[2,3-d]imidazoles, which are important due to their biological properties such as antibiotic, antimalarial, antiparasitic, and antitumor activities. The synthesis was achieved using 2,3-dichloro-1,4-naphthoquinone as the starting material, o-phenylenediamine and benzamidines as nucleophiles, and sodium dodecyl sulfate (SDS) micelles as a catalyst in water. The purpose of these chemicals was to undergo nucleophilic substitution reactions, leading to the formation of the desired benzo[a]phenazine and naphtho[2,3-d]imidazole derivatives with excellent yields, demonstrating a green and regio- and chemoselective approach to synthesizing these potentially pharmaceutically significant compounds.

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