229-87-8

Usage

Uses

Used in Biological and Chemical Sensors:
Phenanthridine is used as a dye in biological and chemical sensors, taking advantage of its intercalating properties with DNA.
Used in Ecotoxicity Studies:
Phenanthridine is utilized in the study of ecotoxicity, which involves the evaluation of the effects of toxic substances on living organisms within an ecosystem.
Used in Rotational Spectroscopic Investigations:
Phenanthridine is also employed in rotational spectroscopic investigations, which are essential for understanding molecular structures and their interactions.
Used in Radio Astronomical Searches:
Phenanthridine plays a role in radio astronomical searches, where its properties can be useful for detecting and analyzing celestial objects.
Used in Dye Production:
Ethidium bromide and propidium iodide are examples of intercalating dyes that are based on phenanthridine. These dyes are widely used in various applications, including the visualization of nucleic acids in agarose gels and the staining of nucleic acids in microscopy.

History

Phenanthridine was first discovered by Ame Pictet and H. J. Ankersmit in 1891 by pyrolysis of the condensed product of benzaldehyde and aniline. Earlier, phenanathridine and related compounds were prepared using mainly Pictect-Hurbert and modified Morgan-Walls type of condensation reactions.

Preparation

Palladium catalyzed synthesis of phenanthridine has been accomplished by Pritchard and coworkers from imidoyl selenides. This was the first report of palladium insertion into the C-Se bond. The palladium insertion into the imidoyl selenides 3.20 followed by intramolecular cyclization and subsequent aromatization via the elimination of HSePh lead to the formation of substituted phenanthridines 3.21. Pd-catalysed synthesis of phenanathridine

Synthesis Reference(s)

Journal of the American Chemical Society, 74, p. 6295, 1952 DOI: 10.1021/ja01144a521Journal of Heterocyclic Chemistry, 26, p. 865, 1989 DOI: 10.1002/jhet.5570260366Tetrahedron Letters, 29, p. 5463, 1988 DOI: 10.1016/S0040-4039(00)80787-X

Air & Water Reactions

Sparingly soluble in water.

Reactivity Profile

PHENANTHRIDINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

Flash point data are not available for PHENANTHRIDINE, but is probably combustible.

Safety Profile

Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C13H9N/c1-2-6-12-10(4-1)7-8-11-5-3-9-14-13(11)12/h1-9H

Upstream product

• 1484-12-4 N-methylcarbazole 
• 27799-79-7 5,6-dihydrophenanthridine 
• 62833-92-5 7,8,9,10-tetrahydrophenanthridine 
• 1015-89-0 6(5H)-phenanthridinone 
• 17613-40-0 bromo-6 phenanthridine 
• 758640-21-0 N-Benzylaniline 
• 1689-64-1 9-Fluorenol 
• 108-24-7 acetic anhydride 
• 5346-21-4 N-formyl-2-aminobiphenyl 
• 538-51-2 benzylidene phenylamine 
• 14548-01-7 phenanthridine N-oxide 
• 236-24-8 tetrazolo<1,5>phenanthridine 
• 4706-43-8 1-benzyl-1H-benzotriazole 
• 831-91-4 Benzyl phenyl sulfide 

Downstream Products

• 17613-37-5 2-bromophenanthridine 
• 14548-01-7 phenanthridine N-oxide 
• 4935-85-7 5-(3-trimethylammonio-propyl)-phenanthridinium; dibromide 
• 108977-62-4 6-o-tolyl-5,6-dihydro-phenanthridine 
• 64057-63-2 5-[3-(1-methyl-pyrrolidinium-1-yl)-propyl]-phenanthridinium; dibromide 
• 59193-74-7 5-benzoyl-5,6-dihydrophenanthridine-6-carbonitrile 
• 2720-93-6 6-phenylphenanthridine 
• 47135-83-1 6-(4′-methylphenyl)phenanthridine 
• 5412-06-6 N-methyl phenanthridinium iodide 
• 16573-46-9 6-benzyl-5,6-dihydrophenanthridine 
• 1015-89-0 6(5H)-phenanthridinone 
• 1015-89-0 phenanthridin-6-ol 
• 832-68-8 6-aminophenanthridine 
• 34951-07-0 5-benzoyl-6-(2-oxo-2-thiophen-2-yl-ethyl)-5,6-dihydro-phenanthridine 

Related news

Palladium‐Catalyzed Reaction of MBH Acetates and Terminal Alkynes: Cascade Synthesis of PHENANTHRIDINE (cas 229-87-8) and 6‐ArylethynylPHENANTHRIDINE (cas 229-87-8)09/30/2019

We have described the palladium‐catalyzed regioselective cascade synthesis of phenanthridines and 6‐arylethynylphenanthridines in good to excellent yields from a reaction between Morita–Baylis–Hillman (MBH) acetates and terminal alkynes. These cascade reactions are temperature controlled and...detailed

Relevant academic research and scientific papers

New protocols for the synthesis of 3,4-annulated and 4-substituted quinolines from β-bromo-α,β-unsaturated aldehydes and 1-bromo-2-nitrobenzene or 2-bromoacetanilide

The palladium[0]-mediated Ullmann cross-coupling of readily available β-bromo-α,β-unsaturated aldehydes of the general form 2 with 1-bromo-2-nitrobenzene (3, X = Br) delivers products, 4, that undergo reductive cyclization to novel quinolines (5) upon exposure to indium in aqueous ammonium chloride or to Raney-nickel in the presence of dihydrogen. Analogous cross-coupling of 2-bromoacetanilide (6) with 2 affords products of type 7 that undergo in situ and K2CO3-mediated cyclization to give the same types of quinolines (5).

Azulene–Naphthalene-Type Rearrangements in Benz[a]azulene and Cyclohepta[b]indole

Flash vacuum pyrolysis (FVP) of benz[a]azulene yields phenanthrene and 2-ethynylbiphenyl. FVP of cyclohepta[b]indole similarly yields phenanthridine and 2-cyanobiphenyl. The reversibility of the reactions is demonstrated by FVP of 2-ethynylbiphenyl and 2-isocyanobiphenyl. All the observed reactions are in accord with the norcaradiene–vinylidene mechanism of the azulene–naphthalene rearrangement, whereas other proposed mechanisms are ruled out.

The photochemistry of 6-phenanthridinecarbonitrile I. Product analysis [1]

When 6-phenanthridinecarbonitrile (3) is irradiated at 2537 A in neutral 9:1 2-propanol/water, three major products are formed. These are dimethyl-(6-phenanthridinyl)methanol (4), phenanthridine (5) and 6,6'- biphenanthridine (6). When benzophenone is present in the reaction mixture, diphenyl-(6-phenanthridinyl)methanol is also formed. 6-Phenanthridinyl radical which is common to the formation of all these products, is formed by a monophotonic process involving hydrogen atom abstraction from an alcohol molecule by an excited state of 3. Unlike what is generally found with other nitrogen-heterocycles, the photochemistry of 3 appears to involve only a π,π* singlet state. The fluorescence of 3 is quenched with the triplet quencher cis/trans-piperylene as a function of the concentration of the diene without the accompaniment of an exciplex emission.

Hydride-induced anionic cyclization: An efficient method for the synthesis of 6- H -phenanthridines via a transition-metal-free process

A novel procedure for hydride-induced anionic cyclization has been developed. It includes the reduction of a biaryl bromo-nitrile with a nucleophilic aromatic substitution (SNAr). A range of polysubstituted 6-H-phenanthridines were so obtained in moderate to good yield with good substrate tolerance. This method involves a concise transition-metal-free process and was applied to synthesize natural alkaloids.

Synthesis of phenanthridines and analogues via suzuki coupling and condensation

A convenient and short methodology has been developed towards the synthesis of highly substituted phenanthridines and their analogous benzo[k] and benzo[i] derivatives in a single step via Suzuki coupling and condensation between suitably substituted aromatic ortho-bromoaldehydes and ortho-aminobenzeneboronic acids in good to excellent yields. Georg Thieme Verlag Stuttgart. New York.

LEWIS ACID PROMOTED PHOTOCYCLIZATION OF ARYLIMINES. STUDIES DIRECTED TOWARDS THE SYNTHESIS OF PENTACYCLIC NATURAL PRODUCTS.

Arylimines are converted into 9-azaphenanthrene derivatives (38-46percent) when photolyzed in the presence of boron trifluoride etherate.

Substituent-guided switch between C-H activation and decarboxylative cross-coupling during palladium/copper-catalyzed cascade reactions of 2-aminobenzoates with 2-haloarylaldehydes

Cascade switch: Phenanthridines, pyrazole[4,3-c]quinolines and isocryptolepine were prepared in one step from the Pd/Cu-catalyzed reaction between potassium 2-aminobenzoates and 2-haloarylaldehydes (see scheme). Although the reactions of 2-aminobenzoates proceeded via a cascade imination/C-H functionalization, the reactions of 6-nitro-2-aminobenzoates ensued via a tandem imination/decarboxylative cross-coupling. Copyright

Tert-Butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane: Efficient synthesis of 6-alkyl phenanthridines via C(sp 3)-H/C(sp2)-H bond functionalization

An efficient method for the construction of 6-alkyl phenanthridines by tert-butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane was established. Two new C-C bonds were formed in this reaction via a sequential C(sp3)-H/C(sp2)-H bond functionalization under metal-free conditions. This journal is the Partner Organisations 2014.

Photocyclization synthesis of phenanthridine and its derivatives under direct dehydrogenation conditions

A new method for synthesizing phenanthridines by photocyclization has been established. This method does not require inert gas protection, does not require transition metal catalysts and is environmentally friendly, efficient and convenient. It is proposed to use (E)-N,1-diphenylformimines as substrates to synthesize phenanthridine and its derivatives by ultraviolet light, which provides a new synthesis route for further research on the synthesis of phenanthridines by photocyclization. Eight new phenanthridine compounds were synthesized. The confirmation of their structures provides a material basis for further study of their properties and tapping of their potential for applications. The establishment of this method further broadens the synthetic pathways of phenanthridine compounds.

A ruthenium-catalyzed free amine directed (5+1) annulation of anilines with olefins: Diverse synthesis of phenanthridine derivatives

A ruthenium(ii)-catalyzed cross-ring (5+1) annulation between 2-aminobiphenyls and activated olefins is disclosed for succinct synthesis of valuable phenanthridine scaffolds. The protocol avails a common organic functional group, free amine, as a directing group and represents a unique combination of C-H activation/annulation/C-C bond cleavage cascade that bodes well in the production of bioactive alkaloids including trisphaeridine and bicolorine.