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

Chemical Properties

white to beige powder

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.

Uses

Phenanthridine is an isomeric compound of acridine. It is a nitrogen heterocycle that is the basis of DNA-binding fluorescent dyes through intercalation. Ethidium bromide and propidium iodide are the examples of such intercalating dyes. It is used as a dye in biological and chemical sensors. It is also used in the study of ecotoxicity and rotational spectroscopic investigations and radio astronomical searches.

Definition

ChEBI: Phenanthridine is an azaarene that is the 9-aza derivative of phenanthrene. The parent of the class of phenanthridines. It is a mancude organic heterotricyclic parent, a polycyclic heteroarene, a member of phenanthridines and an azaarene.

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

General Description

Phenanthridine appears as crystalline needles. Mutagenic.

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

• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 538-51-2 benzylidene phenylamine 
• 127876-36-2 2-(benzotriazol-1-yl)acetophenone 
• 180261-80-7 5H-6-azadibenzotetrazolcycloheptene 
• 608090-51-3 2,3-dimethyl-2-(9-methylfluoren-9-yl)-benzothiazoline 
• 608090-48-8 2-(1,1-diphenylethyl)-2,3-dimethyl-benzothiazoline 
• 608090-46-6 2-cumyl-2,3-dimethyl-benzothiazoline 
• 1206-76-4 2-(2'-methoxyphenyl)aniline 
• 126749-30-2 phenanthraquinone monophenylhydrazone 
• 14140-04-6 phenanthrene-9,10-dione oxime 
• 68182-83-2 2'-nitro[1,1'-biphenyl]-2-carbaldehyde 
• 339267-16-2 5-Methoxymethylphenantridin-6(5H)-one 
• 119-61-9 benzophenone 
• 2928-47-4 [1,1′-biphenyl]-2-carbaldehyde oxime 

Downstream Products

• 17613-37-5 2-bromophenanthridine 
• 1015-89-0 6(5H)-phenanthridinone 
• 22364-47-2 6,6-diphenyl-5,6-dihydro-phenanthridine 
• 32317-26-3 7-methyl-6-phenylphenanthridine 
• 15679-03-5 6-chlorophenanthridine 
• 91871-11-3 3-Oxo-1-phenyl-2-oxa-3a-aza-cyclopenta[l]phenanthrene-11b-carbonitrile 
• 91871-12-4 3-Phenyl-pyrrolo[1,2-f]phenanthridine-2-carboxylic acid amide 
• 91871-10-2 phenanthridin-6-yl(phenyl)methanol 
• 91871-07-7 phenanthridin-6-yl(phenyl)methanone 
• 16573-51-6 6-benzyl-phenanthridine 
• 65201-98-1 5-methylphenanthridinium chloride 
• 24160-09-6 6-phenanthridinecarbaldehyde 
• 87861-98-1 5-(4-(trifluoromethyl)benzyl)phenanthridin-6(5H)-one 
• 87861-95-8 5-(4-Trifluoromethyl-benzyl)-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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Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

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