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391573

Sigma-Aldrich

1-Bromopyrene

96%

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About This Item

Empirical Formula (Hill Notation):
C16H9Br
CAS Number:
Molecular Weight:
281.15
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

96%

form

powder

mp

102-105 °C (lit.)

SMILES string

Brc1ccc2ccc3cccc4ccc1c2c34

InChI

1S/C16H9Br/c17-14-9-7-12-5-4-10-2-1-3-11-6-8-13(14)16(12)15(10)11/h1-9H

InChI key

HYGLETVERPVXOS-UHFFFAOYSA-N

General description

1-Bromopyrene, a polycyclic aromatic hydrocarbon (PAH), is a mono bromo substituted pyrene derivative. Its synthesis has been reported. Its gas phase UV-absorption spectra in the UV wavelength range at elevated temperature has been studied. Electron affinitiy (EA) of 1-bromopyrene has been investigated using electron attachment desorption chemical ionization mass spectrometry (DCI-MS) and triple quadrupole tandem mass spectrometry. It participates in the synthesis of novel ruthenium (II) bipyridine or terpyridine complexes bearing pyrene moiety. The reaction of 1-bromopyrene cation radical with water in acetonitrile has been analyzed using the electron transfer stopped-flow (ETSF) method.

Application

1-Bromopyrene is suitable reagent used in the comparative study of effect of substituents of some pyrene derivatives in inducing phototoxicity, DNA damage and repair in human skin keratinocytes and light-induced lipid peroxidation in methanol. It is suitable reagent used in the study to investigate the UV photon-assisted thermal decomposition of PAHs at elevated temperature.
1-Bromopyrene may be used as a standard to compare its spectral properties with that of pyrene based fluorescence probe. It may be used to study the effects of the addition of halogen hetero-atoms on the vapor pressures and thermodynamics of polycyclic aromatic hydrocarbons.
It may be used in the synthesis of the following:
  • 2-methyl-4-pyren-1-yl-but-3-yn-2-ol
  • 1-ethynylpyrene
  • silsesquioxane (SSQ) based hybrid
  • ruthenium nanoparticles functionalized with pyrene moiety
  • mono- and di-pyrenyl perfluoroalkanes
  • oligo(1-bromopyrene)(OBrP) films
  • dinitropyrene-derived DNA adduct

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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Gas-phase UV spectroscopy of anthracene, xanthone, pyrene, 1-bromopyrene and 1, 2, 4-trichlorobenzene at elevated temperatures.
Thony A and Rossi MJ.
Journal of Photochemistry and Photobiology A: Chemistry, 104(1), 25-33 (1997)
Jillian L Goldfarb et al.
The Journal of chemical thermodynamics, 40(3), 460-466 (2008-03-01)
Knowledge of vapor pressures of high molar mass organics is essential to predicting their behavior in combustion systems as well as their fate and transport within the environment. This study involved polycyclic aromatic compounds (PACs) containing halogen hetero-atoms, including bromine
Organic-inorganic hybrids based on pyrene functionalized octavinylsilsesquioxane cores for application in OLEDs.
Mee Yoon Lo et al.
Journal of the American Chemical Society, 129(18), 5808-5809 (2007-04-13)
UV photon-assisted incineration of polycyclic aromatic hydrocarbons at elevated temperatures between 150 and 800?C.
Thony A and Rossi MJ.
Journal of Photochemistry and Photobiology A: Chemistry, 109(3), 267-280 (1997)
Syntheses of mono-and di-pyrenyl perfluoroalkanes.
Wiedenfeld D, et al.
Journal of Fluorine Chemistry, 104(2), 303-306 (2000)

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