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229-87-8 Usage


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.


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.


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.


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.

Check Digit Verification of cas no

The CAS Registry Mumber 229-87-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,2 and 9 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 229-87:
68 % 10 = 8
So 229-87-8 is a valid CAS Registry Number.

229-87-8 Well-known Company Product Price

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  • Sigma

  • (77490)  Phenanthridine  BioReagent, suitable for fluorescence, ≥98.0% (GC)

  • 229-87-8

  • 77490-1G

  • 388.44CNY

  • Detail
  • Aldrich

  • (262692)  Phenanthridine  ≥99%, purified by sublimation

  • 229-87-8

  • 262692-1G

  • 965.25CNY

  • Detail
  • Aldrich

  • (157384)  Phenanthridine  98%

  • 229-87-8

  • 157384-5G

  • 1,343.16CNY

  • Detail



According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017


1.1 GHS Product identifier

Product name phenanthridine

1.2 Other means of identification

Product number -
Other names 3,4-BENZOQUINOLINE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:229-87-8 SDS

229-87-8Related 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

229-87-8Relevant 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

Some, Surajit,Ray, Jayanta K.,Banwell, Martin G.,Jones, Matthew T.

, p. 3609 - 3612 (2007)

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).


Mizuno et al.

, p. 3316 (1973)


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

Chen, Wei-Lin,Chen, Chun-Yuan,Chen, Yan-Fu,Hsieh, Jen-Chieh

, p. 1613 - 1616 (2015)

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.


Thompson, Charles M.,Docter, Stephen

, p. 5213 - 5216 (1988)

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

Cao, Jia-Jia,Zhu, Tong-Hao,Wang, Shun-Yi,Gu, Zheng-Yang,Wang, Xiang,Ji, Shun-Jun

, p. 6439 - 6442 (2014)

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

Chowdhury, Deepan,Dana, Suman,Mandal, Anup,Baidya, Mahiuddin

, p. 11908 - 11911 (2019)

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.


Narasimhan, N. S.,Chandrachood, P. S.,Shete, N. R.

, p. 825 - 827 (1981)

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


de Diesbach,Aeschbach

, p. 1392,1396 (1945)


Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo

supporting information, p. 7738 - 7744 (2021/05/07)

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.

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

Bracher, Franz,Jourjine, Ilya A. P.,Krau?, Jürgen,Zeisel, Lukas

supporting information, p. 2668 - 2679 (2021/11/30)

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.

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