3372-79-0

Basic information

• Product Name: 2,7-dichlorophenazine
• CAS NO: 3372-79-0
• Molecular Formula: C₁₂H₆Cl₂N₂
• Molecular Weight: 249.0954
• Mol File: 3372-79-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 420.9°C at 760 mmHg
• Flash Point: 240.9°C
• Density: 1.482g/cm³
• Vapor Pressure: 6.67E-07mmHg at 25°C
• Refractive Index: 1.742
• CAS DataBase Reference: 2,7-dichlorophenazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-dichlorophenazine(3372-79-0)
• EPA Substance Registry System: 2,7-dichlorophenazine(3372-79-0)

Safety Data

• Hazardous Substances Data: 3372-79-0(Hazardous Substances Data)

Usage

Chemical compound

2,7-dichlorophenazine

Class

aromatic heterocyclic compounds

Structure

phenazine ring with two chlorine atoms attached

Properties

antibacterial, antifungal, electronic, optical

Potential applications

pharmaceuticals, OLEDs, OPVs
Target for researchers in organic synthesis and materials science

Upstream product

• 14933-95-0 N-(4-chlorophenyl)benzenesulfenamide 
• 110-83-8 cyclohexene 
• 100-00-5 4-chlorobenzonitrile 
• 693-02-7 hex-1-yne 
• 75-05-8 acetonitrile 
• 85193-48-2 2'-(p-chlorophenyl)amino-4'-chloro-2-nitrobenzenesulfenanilide 
• 88047-02-3 4-chloro-N²-(4-chlorophenyl)-N¹,N²-bis(2-nitrophenylthio)-o-phenylenediamine 
• 51343-01-2 4'-chloro-2-nitrobenzenesulphenanilide 
• 303-83-3 phenazine 5,10-dioxide 

Downstream Products

• 19036-40-9 2,7-diphenylphenazine 
• 24890-66-2 5,10-dioxy-phenazine-2,7-diol 
• 2089-15-8 2,7-Dichlor-phenazin-5,10-dioxid 

Relevant articles and documents

2-Nitroso-N-arylanilines: Products of acid-promoted transformation of σH adducts of arylamines and nitroarenes

Anions generated from arylamines react with substituted nitrobenzenes to form σH adducts, which, under protonation with acetic acid, undergo transformation to 2-nitroso-N-arylamines, susceptible to reduction, condensation and cyclization reactions. Georg Thieme Verlag Stuttgart.

BORON TRIFLUORIDE PROMOTED REACTION OF BENZENESULPHENANILIDES WITH ALKENES

The boron trifluoride-promoted reaction of a series of 3'- and 4'-substituted benzenesulphenanilides (1) with various alkenes has been investigated as a potential synthetic route to arylaminosulphides.The benzenesulphenanilides (1) investigated generally afford arylaminosulphenylation adducts in fair to good yields except for the methoxy-substituted anilides (1e and f), which largely lead to decomposition products under comparable conditions.In all cases examined, the addition proceeds with trans-stereospecificity and, with terminal alkenes, leads regioselectively to the exclusive (or predominant) formation of the terminal sulphides.The findings are interpreted by assuming that boron trifluoride transforms the sluggish benzenesulphenanilides (1) into reactive electrophilic species, which can undergo nucleophilic attack at sulphur by an alkene, presumably affording episulphonium-borate ion-pair intermediates, in competition with attack by another sulphenanilide unit.

Acid-promoted Decomposition of Benzenesulphenanilides and N-Aryl Bis(benzenesulphen)amides

The decomposition of 4'-substituted benzenesulphanilides (1a-d) in the presence of trifluoroacetic acid (0.6 equiv.) leads to N-arylbis(benzenesulphen)amides (6a-d) in variable yields, depending on the 4'-substituent, in addition to disulphide (4) and anilines (3a-d), whereas products arising from sulphenylation of the N-aryl ring result from 3'-methoxybenzenesulphenanilide (1g).The 4'-nitro- and 3'-nitro-benzenesulphenanilides (1e,f) react with a slight excess of trifluoroacetic acid to give only (4), the thiosulphonate (5), and aniline (3e,f).The findings are interpreted in terms of possible nucleophilic attack at the S-N bond of a protonated sulphenanilide by the nitrogen or the N-aryl ring of another sulphenanilide unit, according to the nature of the substituent and its position, with displacement of aniline (3).The reaction of (1a-d) with 1.5 equiv. of trifluoroacetic acid leads to complete disappearance of the initially formed amides (6a-d) with concomitant formation of phenazines (9) and/or p-quinone di-imines (8).Similar results are obtained by using boron trifluoride-diethyl ether.Di-imines (8) and phenazines (9) are explained on the basis of a mechanism initially involving nucleophilic attack by (1) and/or (6) and/or (3) at the ortho and para positions of an intermediate cation, possibly (18A) or (18B), and loss of the disulphide (4).