229-87-8

Basic information

• Product Name: PHENANTHRIDINE
• Synonyms: 3,4-Benzoisoquinoline;5-azaphenanthrene;6-Phenanthridine;9-Azaphenanthrene;PHENANTHRIDIN;PHENANTHRIDINE;3,4-BENZOQUINOLINE;BENZO[C]QUINOLINE
• CAS NO: 229-87-8
• Molecular Formula: C₁₃H₉N
• Molecular Weight: 179.22
• EINECS: 205-934-4
• Mol File: 229-87-8.mol
• Article Data: 117

Chemical Properties

• Melting Point: 104-107 °C(lit.)
• Boiling Point: 349 °C769 mm Hg(lit.)
• Flash Point: 100 °C
• Appearance: White to beige/Powder
• Density: 1.1255 (rough estimate)
• Vapor Pressure: 0.000166mmHg at 25°C
• Refractive Index: 1.7270 (estimate)
• Solubility: phosphate buffer: soluble
• PKA: 5.58(at 20℃)
• Water Solubility: 0.3g/L(20 oC)
• BRN: 120204
• CAS DataBase Reference: PHENANTHRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENANTHRIDINE(229-87-8)
• EPA Substance Registry System: PHENANTHRIDINE(229-87-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: SF7928000
• Hazardous Substances Data: 229-87-8(Hazardous Substances Data)

Usage

Description

Phenanthridine is an azaarene that is the 9-aza derivative of phenanthrene, making it a mancude organic heterotricyclic parent, a polycyclic heteroarene, and a member of the phenanthridines class. It appears as crystalline needles and is known for its mutagenic properties. Phenanthridine is an isomeric compound of acridine and serves as the basis for DNA-binding fluorescent dyes through intercalation.

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 articles and documents

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).

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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.

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.

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.

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.

SYNTHETIC APPLICATION OF LITHIATION REACTIONS-XIV. NOVEL SYNTHESIS OF 7,8-DIMETHOXY PHENANHRIDINE

The difficultly accessible 7,8-dimethoxy phenenthridine has been synthesised by organolithiation reaction in simple steps and in good yield.

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Radical Borylative Cyclization of Isocyanoarenes with N-Heterocyclic Carbene Borane: Synthesis of Borylated Aza-arenes

Borylated aza-arenes are of great importance in the area of organic synthesis. A radical borylative cyclization of isocyanoarenes with N-heterocyclic carbene borane (NHC-BH3) under metal-free conditions was developed. The reaction allows the efficient assembly of several types of borylated aza-arenes (phenanthridines, benzothiazoles, etc.), which are difficult to access using alternative methods. Mild reaction conditions, a good functional-group tolerance, and generally good efficiencies were observed. The utility of these products is demonstrated, and the mechanism is discussed.

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible N-methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further utilized in the first total synthesis of the natural product nobilone.