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391425

Sigma-Aldrich

1-Acetylpyrene

97%

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About This Item

Empirical Formula (Hill Notation):
C18H12O
CAS Number:
Molecular Weight:
244.29
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

solid

mp

86-89 °C (lit.)

SMILES string

CC(=O)c1ccc2ccc3cccc4ccc1c2c34

InChI

1S/C18H12O/c1-11(19)15-9-7-14-6-5-12-3-2-4-13-8-10-16(15)18(14)17(12)13/h2-10H,1H3

InChI key

KCIJNJVCFPSUBQ-UHFFFAOYSA-N

General description

1-Acetylpyrene is a pyrene derivative. Its synthesis has been reported. Its phytophysical properties have been studied using absolute fluorescence quantum yield measurement and time-dependent density functional theory (TD-DFT) calculations. Its ability to interact with human cytochromes P450 2A13, 2A6, and 1B1 and enzyme inhibition has been reported. Its function as an environment-sensitive fluorophore has been investigated.

Application

1-Acetylpyrene is suitable for use in a comparative study on the photoinitiating efficiency of pyrene, 1-acetylpyrene and 1-(bromoacetyl)pyrene for copolymerization of styrene with acrylonitrile. It may be used in the following studies:
  • As a starting material in the synthesis of ethynlypyrene. 1-(1-chlorovinyl)pyrene was also isolated during this reaction.
  • As a starting material in the synthesis of substituted pyrene derivatives incorporated heterocyclic and sugar moieties.
  • Synthesis of (E)-pyrene oxime ester conjugates of carboxylic acids.
  • Synthesis of tertiary alcohols based on 1-acetylpyrene.
  • Synthesis of (E)-N-[1-(pyren-1-yl)ethylidene]chrysene-2-amine.
  • Synthesis of 3,3-di(methylsulfanyl)-1-(1-pyrenyl)-2-propen-1-one.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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H Surya Prakash Rao et al.
Beilstein journal of organic chemistry, 3, 31-31 (2007-10-02)
The cycloaddition of the von Leusen's reagent (p-tolylsulfonyl)methyl isocyanide (TosMIC) to alpha-aroylketene dithioacetals (AKDTAs) in the presence of sodium hydride in THF at rt resulted in a facile synthesis of the 4-aroyl-3-methylsulfanyl-2-tosylpyrroles 3 in good yield along with a minor
Tertiary alcohols based on 1-acetylpyrene.
Dikusar EA.
Russ. J. Org. Chem., 43(10), 1492-1494 (2007)
One-pot synthesis of 1-acetylpyrene over supported phosphotungstic heteropoly acid catalysts.
He MQ, et al.
Reaction Kinetics, Mechanisms and Catalysis, 108(2), 531-544 (2013)
Tsutomu Shimada et al.
Chemical research in toxicology, 26(4), 517-528 (2013-02-26)
A total of 68 chemicals including derivatives of naphthalene, phenanthrene, fluoranthene, pyrene, biphenyl, and flavone were examined for their abilities to interact with human P450s 2A13 and 2A6. Fifty-one of these 68 chemicals induced stronger Type I binding spectra (iron
Fundamental photoluminescence properties of pyrene carbonyl compounds through absolute fluorescence quantum yield measurement and density functional theory.
Niko Y, et al.
Tetrahedron, 68(31), 6177-6185 (2012)

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