213-46-7

Basic information

• Product Name: PICENE
• Synonyms: Dibenzo(a,i)phenanthrene;Pycene;PICENE;Picene (purity);39453, Picene (purity);Picene (purified by sublimation);Picene (purified by sublimation) (>99.9%);Picene
• CAS NO: 213-46-7
• Molecular Formula: C₂₂H₁₄
• Molecular Weight: 278.35
• EINECS: 205-918-7
• Product Categories: Alphabetic;P;PER - POLA;OLED
• Mol File: 213-46-7.mol
• Article Data: 20

Chemical Properties

• Melting Point: 366-367°
• Boiling Point: bp 518-520°
• Flash Point: 264.5°C
• Appearance: /
• Density: 1.1489 (estimate)
• Vapor Pressure: 2.34E-10mmHg at 25°C
• Refractive Index: 1.8120 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Water Solubility: 2.5ug/L(27 oC)
• Merck: 14,7396
• CAS DataBase Reference: PICENE(CAS DataBase Reference)
• NIST Chemistry Reference: PICENE(213-46-7)
• EPA Substance Registry System: PICENE(213-46-7)

Safety Data

• RIDADR: 2811
• RTECS: TJ3700000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 213-46-7(Hazardous Substances Data)

Usage

Description

Picene, a polycyclic aromatic hydrocarbon (PAH) of environmental relevance has recently been predicted to be carcinogenic, based on quantum mechanical calculation, although in several animal studies no carcinogenicity could be detected. Picene, a hydrocarbon found in the pitchy residue obtained in the distillation of peat-tar and of petroleum. This is distilled to dryness and the distillate repeatedly recrystallized from cymene It may be synthetically prepared by the action of anhydrous aluminium chloride on a mixture of naphthalene and ethylene dibromide, or by distilling α-dinaphthostilbene. It crystallizes in large colourless plates wi hich possess a blue fluorescence It is soluble in concentrated sulphuric acid with a green colour. Chromic acid in glacial acetic acid solution oxidizes it to picene-quinone, picene-quinone carboxylic acid, and finally to phthalic acid. When heated with hy driodic acid and phosphorus it forms hydrides of composition C22H34 and C22H36.

Definition

ChEBI: An ortho-fused polycyclic arene consisting of five fused benzene rings. It is obtained during the distillation of petroleum.

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

• 1233-36-9 (E)-1,2-bis(1-naphthyl)ethene 
• 24743-18-8 picene-13,14-dione 
• 81-25-4 cholic acid 
• 699018-25-2 1-phenethyl-3,4-dihydro-phenanthrene 
• 860549-64-0 1-(2-methyl-phenethyl)-3,4-dihydro-phenanthrene 
• 861018-88-4 6,6a,14,14a-tetrahydro-5H-picen-13-one 
• 856833-56-2 2,3,4,9,10,11-hexahydro-picene-1,12-dione 
• 115163-28-5 4,4a,5,6-tetrahydro-3H-picen-2-one 
• 90-12-0 1-Methylnaphthalene 
• 91-20-3 naphthalene 
• 106-93-4 ethylene dibromide 
• 1233-36-9 1,1'-cis-ethene-1,2-diyl-bis-naphthalene 
• 130800-14-5 C₂₂H₃₀O₂ 
• 70610-53-6 3,4-dihydro-1-vinylphenanthrene 

Downstream Products

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

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 articles and documents

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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.

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

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.