54811-16-4

Basic information

• Product Name: 1,6-dibenzoylpyrene
• Synonyms: 1,6-dibenzoylpyrene
• CAS NO: 54811-16-4
• Molecular Formula: C₃₀H₁₈O₂
• Molecular Weight: 410.46272
• Mol File: 54811-16-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,6-dibenzoylpyrene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-dibenzoylpyrene(54811-16-4)
• EPA Substance Registry System: 1,6-dibenzoylpyrene(54811-16-4)

Safety Data

• Hazardous Substances Data: 54811-16-4(Hazardous Substances Data)

Usage

Chemical structure

1,6-dibenzoylpyrene is a polycyclic aromatic hydrocarbon (PAH) compound with a benzene ring fused to a pyrene moiety and two benzoyl groups attached to the 1 and 6 positions.

Toxicity

It is a highly toxic chemical, posing significant health risks to humans and the environment.

Carcinogenicity

1,6-dibenzoylpyrene is classified as a carcinogenic substance, meaning it can cause cancer.

Environmental presence

This compound is commonly found in environmental pollutants, tobacco smoke, and charbroiled foods.

Health issues

Exposure to 1,6-dibenzoylpyrene has been linked to various health problems, including respiratory issues, skin irritation, and cancer.

Hazardous substance

It is considered a hazardous substance and should be handled with extreme care in industrial and laboratory settings.

Regulatory efforts

Ongoing efforts are being made to reduce and regulate the presence of 1,6-dibenzoylpyrene in the environment to mitigate its harmful effects on human health and the ecosystem.

Upstream product

• 129-00-0 pyrene 
• 98-88-4 benzoyl chloride 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 7376-03-6 phenylpyren-1-yl-methanone 
• 71-43-2 benzene 
• 55009-76-2 1,8-dibenzoylpyrene 

Downstream Products

• 202974-49-0 1,6-bis-(α-hydroxy-benzhydryl)-pyrene 
• 55009-74-0 1,6-dibenzyl-pyrene 
• 128-70-1 pyranthrone 
• 858268-25-4 1,6-dibenzoyl-3,8-dibromo-pyrene 
• 1616620-24-6 C₃₀H₂₂O₂ 
• 129-00-0 pyrene 
• 7376-03-6 phenylpyren-1-yl-methanone 
• 7267-89-2 8H-dibenzo[def,qr]chrysen-8-one 
• 7267-90-5 11H-indeno[2,1-a]-pyren-11-one 
• 55009-76-2 1,8-dibenzoylpyrene 
• 71-43-2 benzene 

Relevant articles and documents

In quest of reversibility of Friedel-Crafts acyl rearrangements in the pyrene series

Friedel-Crafts acyl rearrangements in PPA of diacetylpyrenes (80–120 °C), dibenzoylpyrenes (80–200 °C), and bis(4-flurobenzoyl)pyrenes (80–120 °C) and Scholl reactions in AlCl3/NaCl of dibenzoylpyrenes (140–200 °C) have been studied. The substrates were 1-AcPY, 2-AcPY, 1,3-Ac2PY, 1,6-Ac2PY, 1,8-Ac2PY, 2,7-Ac2PY, 1-BzPY, 1,6-Bz2PY, 1,8-Bz2PY, 1-4FBzPY, 1,6-4FBz2PY, 1,8-4FBz2PY. The mixtures of pyrene, 1-AcPY, 2-AcPY, 1,3-Ac2PY, 1,6-Ac2PY, 1,8-Ac2PY, and 2,7-Ac2PY were separated by HPLC. The following reversible intermolecular isomerizations were established: 1,6-Ac2PY ? 1,8-Ac2PY, 1,6-Bz2PY ? 1,8-Bz2PY, and 1,6-4'FBz2PY ? 1,8-4'FBz2PY, albeit not in high yields. The results substantiate Gore’s 1955 proposition that “The Friedel–Crafts acylation reaction of reactive aromatic hydrocarbons is a reversible process.” The isomerizations reported here differ from the few previously reported completely reversible intramolecular Friedel-Crafts acyl rearrangements. At ≥ 140 °C, in PPA and in AlCl3/NaCl, 1,6-Bz2PY and 1,8-Bz2PY underwent a highly regioselective double Scholl reaction to give pyranthrone (3) and deacylations to 1-BzPy (and pyrene), followed by mono-Scholl reactions to give 8H-dibenzo[def,qr]chrysen-8-one (1), and 11H-indeno[2,1-a]pyren-11-one (2). The formation of 3 and not the expected tribenzo[a,ghi,o]perylene-7,16-dione (4) from 1,8-Bz2PY indicates that 1,8-Bz2PY has first undergone isomerization to 1,6-Bz2PY. The present study confirms the linkage between Friedel-Crafts acyl rearrangements and the Scholl reaction.

MONOMER FOR HARDMASK COMPOSITION AND HARDMASK COMPOSITION INCLUDING THE MONOMER AND METHOD OF FORMING PATTERNS USING THE HARDMASK COMPOSITION

A monomer for a hardmask composition represented by the following Chemical Formula 1,