226-88-0

Basic information

• Product Name: BENZO[A]TETRACENE
• Synonyms: BENZO[A]TETRACENE;benzo[a]naphthacene;3,4-BENZONAPHTHACENE;Dibenzo[a,i]athracene
• CAS NO: 226-88-0
• Molecular Formula: C₂₂H₁₄
• Molecular Weight: 278.35
• EINECS: 205-932-3
• Mol File: 226-88-0.mol

Chemical Properties

• Melting Point: 263.85°C
• Boiling Point: 356.16°C (rough estimate)
• Flash Point: 264.5 °C
• Appearance: /
• Density: 1.1489 (estimate)
• Vapor Pressure: 1.41E-10mmHg at 25°C
• Refractive Index: 1.8120 (estimate)
• CAS DataBase Reference: BENZO[A]TETRACENE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZO[A]TETRACENE(226-88-0)
• EPA Substance Registry System: BENZO[A]TETRACENE(226-88-0)

Safety Data

• Hazardous Substances Data: 226-88-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Light-Emitting Diodes (OLED) Industry:
BENZO[A]TETRACENE is used as a blue organic semiconductor in OLEDs for its ability to emit blue light. Its use in this industry is due to its favorable electronic properties, which contribute to the efficiency and performance of the devices.
Used in Organic Photovoltaic Devices (OPV) Industry:
In the OPV industry, BENZO[A]TETRACENE is utilized as a component in the active layer of the solar cells. Its role is to enhance the light absorption and charge transport properties, thereby improving the overall efficiency of the photovoltaic devices.
Used in Optoelectronic Applications:
BENZO[A]TETRACENE is being researched for its potential use as a luminescent material in optoelectronic applications. Its unique optical properties make it a candidate for developing advanced light-emitting and light-detecting devices.
Used in Organic Field-Effect Transistors (OFET) and Other Organic Electronic Devices:
Due to its electronic properties, BENZO[A]TETRACENE is being studied for its potential use in organic field-effect transistors and other organic electronic devices. Its application in these areas is aimed at enhancing the performance and functionality of these devices.
However, it is important to note that BENZO[A]TETRACENE, like other polycyclic aromatic hydrocarbons, is considered a potential environmental and health hazard due to its carcinogenic and mutagenic properties. Therefore, proper handling and safety measures should be taken during its use in various applications.

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

Upstream product

• 85-01-8 phenanthrene 
• 933-88-0 ortho-toluoyl chloride 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 86-52-2 1-Chloromethylnaphthalene 
• 91-57-6 2-Methylnaphthalene 
• 2243-83-6 2-naphthaloyl chloride 
• 2506-41-4 1-chloromethylnaphthalene 
• 573-98-8 dimethyl-1,2 naphtalene 
• 103224-49-3 1,3-bis(trimethylsilyl)naphto<1,2-c>furan 
• 5343-99-7 1,2-naphthalenedicarboxylic anhydride 
• 859197-18-5 [3]phenanthryl-o-tolyl ketone 
• 103224-50-6 7,14-bis(trimethylsilyl)-7,14-dihydro-7,14-epoxybenzonaphthacene 
• 3719-43-5 dibenzo[a,h]anthracene-7,14-dione 

Downstream Products

• 65492-95-7 benzo[a]naphthacene-8,13-dione 
• 860563-83-3 benzo[a]naphthacene-5,6,8,13-tetraone 

Relevant articles and documents

A Free-Radical Prompted Barrierless Gas-Phase Synthesis of Pentacene

A representative, low-temperature gas-phase reaction mechanism synthesizing polyacenes via ring annulation exemplified by the formation of pentacene (C22H14) along with its benzo[a]tetracene isomer (C22H14) is unraveled by probing the elementary reaction of the 2-tetracenyl radical (C18H11.) with vinylacetylene (C4H4). The pathway to pentacene—a prototype polyacene and a fundamental molecular building block in graphenes, fullerenes, and carbon nanotubes—is facilitated by a barrierless, vinylacetylene mediated gas-phase process thus disputing conventional hypotheses that synthesis of polycyclic aromatic hydrocarbons (PAHs) solely proceeds at elevated temperatures. This low-temperature pathway can launch isomer-selective routes to aromatic structures through submerged reaction barriers, resonantly stabilized free-radical intermediates, and methodical ring annulation in deep space eventually changing our perception about the chemistry of carbon in our universe.

Cycloadducts of Arynes with 1,3-Bis(trimethylsilyl)naphthofuran: Formation of Novel Polycyclic Aromatic Derivatives and Related Reactions

A recently developed procedure for the preparation of trimethylsilylated isobenzofurans and the use of these materials in cycloaddition reactions has been extended to an isonaphthofuran analogue.The 1,3-bis(trimethylsilyl)naphthofuran (7) has been isolated; its reaction with maleic anhydride in room temperature is rapid and readily reversible as shown by endo to exo cycloadduct interconversion.The failure of 7 to give cycloadduct with 2-butenolide indicates that it is less reactive than the parent naphthofuran.In situ generation and cycloaddition reactions with various arynes (benzyne, 4-methylbenzyne, 3,4-pyridyne, 9,10-phenanthrolyne, 1,2-naphthalyne, 2,3-naphthalyne) are described.The three unsymmetrical arynes all give mixtures of cycloadducts indicative of negligible regioselectivity in Diels-Alder reactions with 7; thus, in spite of possible steric hindrance the reaction with 1,2-naphthalyne gives a 1:1 mixture of dibenz- and dibenzanthracene derivatives.In contrast, the reaction of 1-ethoxy-3-(trimethylsilyl)naphthoanthracene derivative.Various reactions of the cycloadducts are described.