Phenazine, 5-oxide

Base Information

• Chemical Name: Phenazine, 5-oxide
• CAS No.: 304-81-4
• Molecular Formula: C12H8 N2 O
• Molecular Weight: 196.208
• Hs Code.: 2933990019
• European Community (EC) Number: 636-565-0
• NSC Number: 202998,21665
• UNII: 96567H578Y
• DSSTox Substance ID: DTXSID70184482
• Nikkaji Number: J3.634J
• Wikidata: Q27271868
• Mol file: 304-81-4.mol

Synonyms:Phenazine oxide;Phenazine-N-oxide;PHENAZINE, 5-OXIDE;Phenazine 5-oxide;304-81-4;Phenazine N-oxide;N-Oxyphenazine;Phenazin;Phenazin-5-oxide;Phenazine monooxide;Phenazine 9-oxide;N-Oxide de phenazine;Phenazine, N-monoxide;Phenazine mono-N-oxide;Phenazin oxide;Phenazine-9-oxide;Phenazine-5N-oxide;CCRIS 9113;N-Oxide de phenazine [French];PZ-13;NSC 21665;NSC-21665;NSC 202998;NSC-202998;BRN 0150977;AI3-15396;WLN: T C666 BN INJ BO;5-oxidophenazin-5-ium;SCHEMBL51330;CBDivE_002663;DTXSID70184482;UNII-96567H578Y;NSC21665;NSC202998;AKOS003625394;LS-103022;96567H578Y;FT-0748018;4-23-00-01657 (Beilstein Handbook Reference);Q27271868

Chemical Property of Phenazine, 5-oxide

Chemical Property:

• Vapor Pressure: 2.23E-06mmHg at 25°C
• Melting Point: 226.5°C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 404.3°Cat760mmHg
• PKA: 0.45±0.30(Predicted)
• Flash Point: 198.3°C
• PSA: 38.35000
• Density: 1.28g/cm³
• LogP: 2.81650
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 196.063662883
• Heavy Atom Count: 15
• Complexity: 212

Purity/Quality:

99.5% ^*data from raw suppliers

PHENAZINE-N-OXIDE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)N=C3C=CC=CC3=[N+]2[O-]

Technology Process of Phenazine, 5-oxide

There total 13 articles about Phenazine, 5-oxide 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: 70.0%

benzofurazan (273-09-6) + Diphenyliodonium triflate (66003-76-7) → Phenazin-mono-N-Oxyd (304-81-4)

Guidance literature:

With copper(I) bromide; In 1,2-dichloro-ethane; at 70 ℃; for 24h; regioselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.8b01748

Reference yield: 52.0%

Phenazin (92-82-0) → Phenazin-mono-N-Oxyd (304-81-4) + phenazine 5,10-dioxide (303-83-3)

Guidance literature:

With magnesium monoperoxyphthalate hexahydrate; In acetic acid; at 85 ℃; for 1h;

Reference yield:

2-nitro-aniline (88-74-4) → Phenazin-mono-N-Oxyd (304-81-4)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hydroxide; sodium hypochlorite / ethanol; water / 0 °C / Sealed tube; Inert atmosphere

2: triethyl phosphite / tetrahydrofuran / 7 h / 60 °C / Inert atmosphere; Sealed tube

3: copper(I) bromide / 1,2-dichloro-ethane / 24 h / 70 °C / Sealed tube; Inert atmosphere

With sodium hypochlorite; potassium hydroxide; copper(I) bromide; triethyl phosphite; In tetrahydrofuran; ethanol; water; 1,2-dichloro-ethane;

DOI:10.1021/acs.orglett.8b01748

upstream raw materials:

Phenazin

aniline

bis(2-nitrophenyl)ether

N-acetyl-N-phenyl-o-nitroaniline

Downstream raw materials:

3,7-dinitro-phenazine-5-oxide

1,7-dinitro-phenazine-5-oxide

trans-dichloro(ethylene)(phenazine N-oxide)platinum

Phenazin

Refernces

• 1、 Maki et al.. "-". . p. 693. Retrieved 1972.
• 2、 Fasani, Elisa,Pietra, Silvio,Albini, Angelo. "THE PHOTOCYCLIZATION OF N-ACYL-2-NITRODIPHENYLAMINES TO PHENAZINE N-OXIDES: SCOPE AND MECHANISM". . p. 573 - 584. Retrieved 2007/10/02.
• 3、 Acree, W. E.,Tucker, Sheryl A.,Zvaigzne, Anita I.,Meng-Yan, Yang,Pilcher, G.,Ribeiro da Silva, Maria D. M. C.. "Enthalpies of combustion of 2,4,6-trimethylbenzonitrile, 2,4,6-trimethylbenzonitrile N-oxide, 2,6-dimethylbenzonitrile, 2,4,6-trimethoxybenzonitrile, and 2,4,6-trimethoxybenzonitrile N-oxide: the dissociation ethalpies of the (N-O) bonds". . p. 31 - 36. Retrieved 2007/10/02.