213-46-7

Usage

Uses

Used in Environmental Studies:
Picene is used as a marker for the presence of PAHs in the environment, as it is a specific indicator of petroleum contamination. Its detection helps in understanding the extent of pollution and the potential health risks associated with exposure to PAHs.
Used in Chemical Research:
Picene is used as a starting material for the synthesis of various organic compounds, such as picene-quinone, picene-quinone carboxylic acid, and phthalic acid. Its unique structure and properties make it a valuable compound for studying the chemical properties and reactions of PAHs.
Used in Analytical Chemistry:
Picene is used as a reference compound for the development and calibration of analytical methods, such as chromatography and mass spectrometry, which are employed for the detection and quantification of PAHs in environmental and biological samples.
Used in Material Science:
Picene's unique structure and properties, such as its blue fluorescence and solubility in concentrated sulfuric acid, make it a potential candidate for the development of new materials with specific optical, electronic, or catalytic properties.

Carcinogenicity

Dermal application of picene in an early design limited study on mice gave negative results for carcinogenicity. More recently, picene gave positive results when tested in three dermal application studies on mice, two of which were initiation–promotion experiments. Subcutaneous injection into newborn and adult mice and young rats gave positive results in mice but negative results in rats.

InChI:InChI=1/C22H14/c1-3-7-17-15(5-1)9-11-21-19(17)13-14-20-18-8-4-2-6-16(18)10-12-22(20)21/h1-14H

Upstream product

• 90-12-0 1-Methylnaphthalene 
• 7446-70-0 aluminium trichloride 
• 91-20-3 naphthalene 
• 107-06-2 1,2-dichloro-ethane 
• 106-93-4 ethylene dibromide 
• 75-15-0 carbon disulfide 
• 15374-45-5 1,2-di(1-naphthyl)ethane 
• 1233-36-9 1,1'-cis-ethene-1,2-diyl-bis-naphthalene 
• 24743-18-8 picene-13,14-dione 
• 71912-49-7 1-(3,4-dihydro-[1]naphthyl)-2-[1]naphthyl-ethane 
• 70610-53-6 3,4-dihydro-1-vinylphenanthrene 
• 118-92-3 anthranilic acid 
• 130800-14-5 C₂₂H₃₀O₂ 
• 115163-28-5 4,4a,5,6-tetrahydro-3H-picen-2-one 

Downstream Products

• 24743-25-7 5,6-Dioxo-5,6-dihydro-picen 
• 24743-18-8 picene-13,14-dione 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 1296211-12-5 5,8-di(phenylthio)picene 
• 1296211-14-7 5,8-diphenylpicene 
• 192-47-2 1.2,4.5,8.9-tribenzopyrene 
• 31617-32-0 11-o-Carboxybenzoylpicene 

Related news

Effective synthesis of diiodinated PICENE (cas 213-46-7) and dibenzo[a,h]anthracene by AuCl-catalyzed double cyclization09/29/2019

6,13-Diiododibenzo[a,h]anthracene and 5,8-diiodopicene were synthesized by AuCl-catalyzed double cyclization. The highly selective reaction yielded a new class of peri-halogenated fused aromatics.detailed

PICENE (cas 213-46-7) thin films on metal surfaces: Impact of molecular shape on interfacial coupling09/28/2019

The energetics at organic‐metal interfaces are, to large extend, determined by the structure of the molecular adsorbate on the substrate surface. As shown by low‐energy electron diffraction (LEED) the zigzag shape of picene leads to a peculiar monolayer structure on Ag(111), Ag(110), and Cu(11...detailed

Relevant academic research and scientific papers

Diels-Alder reactions of arylethenes. Synthesis of some [5]phenacenes and fluorenoanthracenes

A one-pot high yielding route to 3,4-dihydro-1-(2H)-anthracenone (9) based on high pressure Diels-Alder reaction is described. The synthesis of 3,4-dihydro-1-vinylphenanthrene (1) and 3,4-dihydro-1-vinylanthracene (2) is reported. A new synthetic two-step approach to [5]phenacenes and fluorenoanthracenes has been developed. It is based on the Diels-Alder reaction of arylethenes 1 and 2 with benzyne (13), 1,4-benzoquinone (14), 1,4-naphthoquinone (15) and inden-1-one (17) and on the aromatization of the cycloadducts. Structure analysis of the reaction products by 1H and 13C- NMR spectroscopy is presented.

3,3′,5,5′-Tetra- tert -butyl-4,4′-diphenoquinone (DPQ)-Air as a New Organic Photocatalytic System: Use in the Oxidative Photocyclization of Stilbenes to Phenacenes

We report an organic photocatalytic system, namely 3,3′,5,5′-tetra-tert-butyl-4,4′-diphenoquinone (DPQ) and air, capable of coupling efficiently with the photocyclization of stilbenes to afford phenacenes. The potential of this new and mild process is shown with the synthesis of [5]- and [7]phenacene, two semiconductors recently implemented into organic electronic devices, with high yields and remarkable purity.

Preparation of (substituted) picenes via solar light-induced Mallory photocyclization

Picenes 2a-c were readily obtained via photocyclization of dinaphthylethenes 1a-c by a straightforward solar light-induced Mallory reaction. The product was easily recovered by simple filtration after exposure of the reaction mixture to sunlight. The polyene obtained was then characterized by means of Raman spectroscopy and X-ray diffraction.

Oxidative, Iodoarene-Catalyzed Intramolecular Alkene Arylation for the Synthesis of Polycyclic Aromatic Hydrocarbons

A catalytic, metal-free and chemoselective oxidative intramolecular coupling of arene and alkene C?H bonds is reported. The active hypervalent iodine (HVI) reagent, generated catalytically in situ from iodotoluene and meta-chloroperoxybenzoic acid (m-CPBA), reacts with o-vinylbiphenyls to generate polyaromatic hydrocarbons in up to 95 % yield. Experimental evidence suggests the reactions proceed though vinyliodonium and, possibly, vinylenephenonium intermediates.

Sandwich complexes of iron and ruthenium with the semiconducting aromatic hydrocarbon picene

Pentacyclic aromatic hydrocarbon picene C22H14 was synthesized by the improved two-step procedure from 1-naphthaldehyde in ca. 50% total yield. Reaction of picene with ferrocene in the presence of AlCl3 produced the binucl

Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin Metathesis

Polycyclic aromatic hydrocarbons are important structural motifs in organic chemistry, pharmaceutical chemistry, and materials science. The development of a new synthetic strategy toward these compounds is described based on the design principle of iron(III)-catalyzed carbonyl-olefin metathesis reactions. This approach is characterized by its operational simplicity, high functional group compatibility, and regioselectivity while relying on FeCl3 as an environmentally benign, earth-abundant metal catalyst. Experimental evidence for oxetanes as reactive intermediates in the catalytic carbonyl-olefin ring-closing metathesis has been obtained.

Production of [pisen[pisen] and derivatives thereof

PROBLEM TO BE SOLVED: To provide a method of producing a picene and a derivative thereof suitable for uses of organic semiconductors, thin film transistors, field effect transistors or solar batteries or the like, in a short reaction process with high yield.SOLUTION: A method of producing a picene of formula 8 and a derivative thereof includes, as represented compounds and steps, a step 1 to subject a compound of formula 5 and a compound of formula 6 to a coupling reaction for producing a compound of formula 7, and a step 2 to subject the compound of formula 7 to dehydrohalogenation.

Convenient Phenacene Synthesis by Sequentially Performed Wittig Reaction and Mallory Photocyclization Using Continuous-Flow Techniques

Various phenacenes possessing chrysene, picene, and fulminene frameworks were prepared by using a continuous-flow synthetic protocol in which Wittig reaction affording diarylethenes and their Mallory photocyclization producing phenacene skeletons were sequentially performed. The Wittig reaction solution, containing the diaryl ethene obtained from an arylaldehyde and an arylmethyltriphenylphosphonium salt, was mixed with an iodine solution in the flow system and, subsequently, the solution was subjected to the photoreaction. Desired phenacenes were obtained with high to moderate chemical yield. For the present protocol, isolation of the intermediary diarylethene, which is the key precursor of the phenacene, is unnecessary. The approach provides a convenient method to supply a variety of phenacene samples, which are needed for initial systematic surveys in material science.

Base-Promoted/Gold-Catalyzed Intramolecular Highly Selective and Controllable Detosylative Cyclization

A highly selective, controllable and synthetically useful base-promoted intramolecular detosylative cyclization of bis-N-tosylhydrazones has been achieved, affording N-containing heterocycles and cyclic olefins under transition-metal-free or gold-catalyzed procedures, respectively. Moreover, an effective and practical metal-free or gold-catalyzed approach to synthesize polycyclic aromatic compounds is also reported. Basic cyclizations: A highly selective, controllable, and synthetically useful base-promoted intramolecular detosylative cyclization of bis-N-tosylhydrazones affords N-containing heterocycles and cyclic olefins under transition-metal-free or gold-catalyzed procedures, respectively. Moreover, an effective and practical metal-free or gold-catalyzed approach to synthesize polycyclic aromatic compounds is also reported.

Efficient synthetic photocyclization for phenacenes using a continuous flow reactor

The continuous flow reaction technique has been applied to the photocyclization of 1,2-diarylethenes, the so-called Mallory reaction, to afford phenacenes in high chemical yields and efficiencies (114-288mg h-1). The present technique will allow us to produce several grams of phenacenes at a time.