203-80-5

Basic information

• Product Name: phenalene
• Synonyms: phenalene;peri-benznaphthalene;1H-Phenalene;Benzonaphthene;Perinaphthene;Perinaphthindene;peri-Naphthindene
• CAS NO: 203-80-5
• Molecular Formula: C₁₃H₁₀
• Molecular Weight: 166.2185
• EINECS: 205-907-7
• Mol File: 203-80-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 159-160 °C(Solv: ethanol (64-17-5))
• Boiling Point: 316.4 °C at 760 mmHg
• Flash Point: 150.7 °C
• Appearance: /
• Density: 1.139 g/cm³
• Vapor Pressure: 0.000765mmHg at 25°C
• Refractive Index: 1.691
• CAS DataBase Reference: phenalene(CAS DataBase Reference)
• NIST Chemistry Reference: phenalene(203-80-5)
• EPA Substance Registry System: phenalene(203-80-5)

Safety Data

• Hazardous Substances Data: 203-80-5(Hazardous Substances Data)

Usage

General Description

Phenalene is a polycyclic aromatic hydrocarbon (PAH) composed of three fused benzene rings, and is a common constituent of coal tar and other fossil fuels. Its chemical structure consists of ten carbon atoms and eight hydrogen atoms arranged in a series of connected hexagonal rings. Phenalene is a colorless, crystalline solid with a molecular weight of 130.19 g/mol. It is considered to be a potential environmental and human health hazard due to its carcinogenic and mutagenic properties, and is classified as a hazardous air pollutant by the United States Environmental Protection Agency. Phenalene is primarily used as a reference material for analytical purposes and in laboratory research to study the toxicological effects of PAHs.

InChI:InChI=1/C13H10/c1-4-10-6-2-8-12-9-3-7-11(5-1)13(10)12/h1-8H,9H2

Synthetic route

1-hydroxy-2,3-dihydro-1H-phenalene (130292-28-3) → phenalene (203-80-5)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 0.5h; Heating;	99%
Multi-step reaction with 2 steps 1: n-BuLi / hexane; tetrahydrofuran / -80 °C 2: tetrahydrofuran / 0.25 h / -15 °C View Scheme
With hydrogenchloride In ethanol; water Reflux; Inert atmosphere;

chloro-trimethyl-silane (75-77-4) + phenalenyl anion (42464-32-4) → phenalene (203-80-5) + 1-trimethylsilyl-1H-phenalene (71264-27-2)

Conditions	Yield
In tetrahydrofuran at -15℃; for 0.25h;	A n/a B 70.7%

Perinaphthenon (548-39-0) → phenalene (203-80-5)

Conditions	Yield
With diisobutylaluminium hydride In hexane; benzene Heating;	62%
With diisobutylaluminium hydride In hexane; toluene Heating;	40%
With lithium aluminium tetrahydride; diethyl ether at 35℃;
With lithium aluminium tetrahydride; aluminium trichloride
With diisobutylaluminium hydride

tetrachloromethane (56-23-5) + Perinaphthenone hydrazone (6968-74-7) → phenalene (203-80-5)

Conditions	Yield
at 130 - 140℃; im Hochvakuum;

Perinaphthenon (548-39-0) → phenalene (203-80-5) + 1-Phenalenol (91598-47-9)

Conditions	Yield
With sodium tetrahydroborate; cerchloride-hexahydrate In methanol Yield given. Yields of byproduct given;

1,3-perinaphthadiyl biradical (66486-77-9) → phenalene (203-80-5)

Conditions	Yield
at -153.1℃;
at -153.1℃; Kinetics; Thermodynamic data; Ea; var. temp.;

1-Phenalenol (91598-47-9) → phenalene (203-80-5) + Perinaphthenon (548-39-0)

Conditions	Yield
With acetic acid In chloroform-d1 for 0.5h; half-life;

naphthocyclopropane (6840-31-9) → phenalene (203-80-5)

Conditions	Yield
In benzene-d6 Product distribution; Mechanism; thermolysis;

naptho[1’,8a’,8’:bc]-bicyclo[3.1.0]hex-2-ene (6840-31-9) → phenalene (203-80-5)

Conditions	Yield
at 187℃; Kinetics; Thermodynamic data; various temp., also in the presence of O2; Ea, log A, ΔH(excit.), ΔS(excit.);

polyethylene → 9H-fluorene (86-73-7) + phenalene (203-80-5) + 2-methyl-9H-fluorene (1430-97-3) + 3-methylbiphenyl (643-93-6)

Conditions	Yield
With air at 600 - 900℃; Oxidation; Formation of xenobiotics; Further byproducts given;

(+-)-2,3-dihydro-1H-phenalen-1-ol → phenalene (203-80-5)

Conditions	Yield
With hydrogenchloride

1-oxo-phenalene-hydrazone → phenalene (203-80-5)

Conditions	Yield
With sodium hydroxide at 130 - 140℃; Erhitzen im Hochvakuum;

diethyl ether (60-29-7) + Perinaphthenon (548-39-0) + LiAlH4 → phenalene (203-80-5)

Conditions	Yield
at 35℃;

scrap tire → dibenzofuran (132-64-9) + 9H-fluorene (86-73-7) + phenalene (203-80-5) + 1,4,5-trimethylnaphthalene (2131-41-1)

Conditions	Yield
With air at 650 - 850℃; Oxidation; Formation of xenobiotics; Further byproducts given. Title compound not separated from byproducts;

crushed scrap tires → phenalene (203-80-5)

Conditions	Yield
With synthetic air at 750℃; Formation of xenobiotics;
at 750℃; Formation of xenobiotics;

phenalene (203-80-5) + palladium dichloride → {Pd(η3-phenalenyl)Cl}2 (73409-59-3)

Conditions	Yield
With sodium acetate In ethanol; acetic acid To a soln. of phenalene in EtOH cooled in an ice bath a soln. of PdCl2 and sodium acetate in acetic acid was added, stirred for 1 h, then stirred at room temp. for 2 h;; ppt. was filtered, washed with EtOH and ether, dried; elem. anal.;;	93%

lithium tetrachloropalladate + phenalene (203-80-5) → {Pd(η3-phenalenyl)Cl}2 (73409-59-3)

Conditions	Yield
In methanol; water To a soln. of ligand in MeOH-H2O was added a soln. of Li2PdCl4 in MeOH at room temp., the soln. was stirred overnight (N2 atm.);; ppt. was filtered, washed with MeOH and ether, dried; elem. anal.;;	92%
	90%

phenalene (203-80-5) → perinaphthane (479-58-3)

Conditions	Yield
With hydrogen; platinum(IV) oxide In methanol for 48h;	90%
With methanol; palladium Hydrogenation;

trisacetonitrile(tricarbonyl)chromium(0) (16800-46-7, 22736-49-8) + phenalene (203-80-5) → tricarbonyl(6a,7-9,9a,9b-η(6)-phenalene)chromium (73409-60-6, 125915-02-8)

Conditions	Yield
In tetrahydrofuran phenalene and Cr complex were heated at 45°C in THF for 5 h; mixt. was chromd. (Al2O3, hexane/ether 3/1); sublimation; elem. anal.;	21%

phenalene (203-80-5) + trityl cation (13948-08-8) → phenalenylium; perchlorate

Conditions	Yield
With acetic acid

phenalene (203-80-5) → Perinaphthenon (548-39-0)

Conditions	Yield
With air; acetic acid
With chromium(VI) oxide; acetic acid
With aluminum oxide; oxygen 1.) benzene, irradiation; Yield given. Multistep reaction;

phenalene (203-80-5) → phenalenyl (3924-44-5)

Conditions	Yield
With diethyl ether; potassium ethoxide anschliessendes Behandeln mit Sauerstoff;
With oxygen In toluene for 1461h;
With chloranil In benzene
Inert atmosphere;

phenalene (203-80-5) → (+/-)-cis-2,3-dihydro-1H-phenalene-1,2-diol

Conditions	Yield
With osmium(VIII) oxide

phenalene (203-80-5) + phenyllithium (591-51-5) → 4-methyl-1H-phenalene (72814-49-4)

Conditions	Yield
With diethyl ether anschliessende Behandlung mit Methyljodid;

diiodomethane (75-11-6) + phenalene (203-80-5) → Naphtho<1',8'>bicyclo<4.1.0>hept-2-en (54759-24-9)

phenalene (203-80-5) + <5-(dimethylamino)-2,4-pentadienylidene>dimethylammonium perchlorate → 1-<5-Dimethylamino-pentadien-(2,4)-yliden>-phenalen (23842-84-4)

Conditions	Yield
With pyridine; sodium methylate

phenalene (203-80-5) + 1,3-bis-dimethylamino-1-methyl trimethinium ; perchlorate → 1-methylpyrene (2381-21-7)

Conditions	Yield
(i) NaOMe, Py, (ii) quinoline, (heating); Multistep reaction;

phenalene (203-80-5) + 5-(NN-dimethylaminomethylene)-1-(NN-dimethyliminiomethyl)cyclopenta-1,3-diene perchlorate → Azuleno<5.6.7-c.d>phenalen (6580-41-2)

Conditions	Yield
(i) NaOMe, Py, (ii) quinoline, (heating); Multistep reaction;

phenalene (203-80-5) + 1-Dimethylamino-3-dimethylimonio-2-(p-brom-phenyl)-propen-(1)-perchlorat → 2-(4-bromophenyl)pyrene (23801-23-2)

Conditions	Yield
(i) NaOMe, Py, (ii) quinoline, (heating); Multistep reaction;

phenalene (203-80-5) + 3-α-naphthyl-1,1,5,5-tetramethyl-1H-1,5-diazapentadienium perchlorate → 1-(2-pyrenyl)naphthalene (23801-24-3)

Conditions	Yield
(i) NaOMe, Py, (ii) quinoline, (heating); Multistep reaction;

phenalene (203-80-5) + 3-β-naphthyl-1,1,5,5-tetramethyl-1H-1,5-diazapentadienium perchlorate → 2-<β-Naphthyl>-pyren (23801-25-4)

Conditions	Yield
(i) NaOMe, Py, (ii) quinoline, (heating); Multistep reaction;

phenalene (203-80-5) + ((Z)-3-Dimethylamino-2-phenyl-allylidene)-dimethyl-ammonium; perchlorate (7089-34-1) → 2-phenyl-pyrene (5101-28-0)

Conditions	Yield
(i) NaOMe, Py, (ii) quinoline, (heating); Multistep reaction;

phenalene (203-80-5) + 1.3-Bis-(dimethylamino)-1-phenyl-trimethinium-perchlorat → 1-phenyl pyrene (5101-27-9)

Conditions	Yield
(i) NaOMe, Py, (ii) quinoline, (heating); Multistep reaction;

phenalene (203-80-5) + 3-p-chlorophenyl-1,1,5,5-tetramethyl-1H-1,5-diazapentadienium perchlorate → 2-(p-Chlor-phenyl)-pyren (23801-22-1)

Conditions	Yield
(i) NaOMe, Py, (ii) quinoline, (heating); Multistep reaction;

phenalene (203-80-5) + 1,5-Diaza-1,5-diphenyl-1,5-dimethyl-1H-pentadienium perchlorate → 1-<3-(N-Methyl-anilino)-propen-(2)-yliden>-phenalen (23801-02-7)

Conditions	Yield
With pyridine; sodium methylate

phenalene (203-80-5) + 1,3-bis-dimethylaminotrimethinium perchlorate (1611-78-5) → 1-<3-Dimethylamino-propen-(2)-yliden>-phenalen (6580-42-3)

Conditions	Yield
With pyridine; sodium methylate

phenalene (203-80-5) + 3-p-methoxyphenyl-1,1,5,5-tetramethyl-1H-1,5-diazapentadienium perchlorate → 2-(4-methoxyphenyl)pyrene (23801-21-0)

Conditions	Yield
(i) NaOMe, Py, (ii) quinoline, (heating); Multistep reaction;

phenalene (203-80-5) + <2-chloro-3-dimethylamino-2-propenylidene>dimethylammonium perchlorate (2009-80-5) → 2-chloropyrene (784-02-1)

Conditions	Yield
(i) NaOMe, Py, (ii) quinoline, (heating); Multistep reaction;

phenalene (203-80-5) + (7-dimethylamino-2,4,6-heptatrienylidene)dimethylammonium perchlorate → 1-<7-Dimethylamino-heptatrien-(2,4,6)-yliden>-phenalen (23801-01-6)

Conditions	Yield
With pyridine; sodium methylate

phenalene (203-80-5) + 1,5-bis-(N-methyl-anilino)-pentamethinium ; perchlorate → 1-<5-(N-Methyl-anilino)-pentadien-(2,4)-yliden>-phenalen (23801-03-8)

Conditions	Yield
With pyridine; sodium methylate

phenalene (203-80-5) + 1-Dimethylamino-3-dimethylimonio-1-ethyl-propen-(1)-perchlorat → 1-ethylpyrene (17088-22-1)

Conditions	Yield
(i) NaOMe, Py, (ii) quinoline, (heating); Multistep reaction;

Upstream product

• 56-23-5 tetrachloromethane 
• 6968-74-7 Perinaphthenone hydrazone 
• 66486-77-9 1,3-perinaphthadiyl biradical 
• 130292-28-3 2,3-dihydro-1-hydroxy-1H-phenalene 
• 6840-31-9 naptho[1’,8a’,8’:bc]-bicyclo[3.1.0]hex-2-ene 
• 75-77-4 chloro-trimethyl-silane 
• 42464-32-4 phenalenyl anion 
• 60-29-7 diethyl ether 
• 548-39-0 Perinaphthenon 
• 6840-31-9 naphthocyclopropane 
• 91598-47-9 1-Phenalenol 

Downstream Products

• 479-58-3 perinaphthane 
• 2381-21-7 1-methylpyrene 
• 3442-78-2 2-methylpyrene 
• 98-82-8 Isopropylbenzene 
• 3924-44-5 phenalenyl 
• 23842-85-5 2-Cyclohexen-⁽¹⁾-yl-pyren 
• 17088-22-1 1-ethylpyrene 
• 23801-03-8 1-<5-(N-Methyl-anilino)-pentadien-(2,4)-yliden>-phenalen 
• 23801-21-0 2-(4-methoxyphenyl)pyrene 
• 23801-02-7 1-<3-(N-Methyl-anilino)-propen-(2)-yliden>-phenalen 
• 23801-22-1 2-(p-Chlor-phenyl)-pyren 
• 5101-27-9 1-phenyl pyrene 
• 5101-28-0 2-phenyl-pyrene 
• 23801-23-2 2-(4-bromophenyl)pyrene 

Related news

The isomers of phenalene (cas 203-80-5) and their singlet and triplet states: A Hartree–Fock and density functional computational investigation09/29/2019

Each of the isomers of phenalene, 1H-, 2H-, 3aH-, and 9bH-phenalene, as well as the cation, neutral radical, and anion in the phenalenyl system, have been examined at the Hartree–Fock 6-31G(d) and the density functional B3LYP/6-31G(d) levels of theory. The structures and properties of the phena...detailed

Relevant articles and documents

Hydrogenation and dehydrogenation reactions of the phenalenyl radical/1H-phenalene system at low temperatures

Phenalenyl radical was generated in situ in inert matrices by laser UV photolysis of 1H-phenalene, and was identified by recording laser induced fluorescence and IR spectra. Theoretical computations predict that the H atom addition to phenalenyl radical is barrierless, while the H atom abstraction from 1H-phenalene has only a small barrier. Upon annealing the Xe matrix after the photolysis, the radical and the H atom recombine, while H atom abstraction from 1H-phenalene is a possible explanation for additional spectral changes. These results show that the phenalenyl radical/1H-phenalene system can be a very effective catalyst in the formation of interstellar H2.

Carbon Acidity. 62. Equilibrium Acidities of Some Phenalene Hydrocarbons: SCF-? MO Correlation

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Spectroscopy of the free phenalenyl radical

After benzene and naphthalene, the smallest polycyclic aromatic hydrocarbon bearing six-membered rings is the threefold-symmetric phenalenyl radical. Despite the fact that it is so fundamental, its electronic spectroscopy has not been rigorously scrutinized, in spite of growing interest in graphene fragments for molecular electronic applications. Here we used complementary laser spectroscopic techniques to probe the jet-cooled phenalenyl radical in vacuo. Its spectrum reveals the interplay between four electronic states that exhibit Jahn-Teller and pseudo-Jahn-Teller vibronic coupling. The coupling mechanism has been elucidated by the application of various ab initio quantum-chemical techniques.

Evolution of products in the combustion of scrap tires in a horizontal, laboratory scale reactor

A horizontal laboratory reactor was used to study the evolution of byproducts from the combustion of scrap tires at five nominal temperatures (ranging from 650 to 1050 °C) and different oxygen:sample ratios A model was used to calculate the bulk air ratio (λ), and the oxygen consumption was discussed considering this ratio λ. More than 100 volatile and semivolatile compounds were identified and quantified by gas chromatography mass spectrometry, plotting their yields vs the bulk air ratio and temperature. Five different behaviors considering the bulk air ratio and the temperature were identified.