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Key Documents

391573

Sigma-Aldrich

1-Bromopyrene

96%

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About This Item

Formule empirique (notation de Hill):
C16H9Br
Numéro CAS:
Poids moléculaire :
281.15
Numéro MDL:
Code UNSPSC :
12352100
ID de substance PubChem :
Nomenclature NACRES :
NA.22

Niveau de qualité

Pureté

96%

Forme

powder

Pf

102-105 °C (lit.)

Chaîne SMILES 

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

Clé InChI

HYGLETVERPVXOS-UHFFFAOYSA-N

Description générale

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

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves


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Consulter la Bibliothèque de documents

Electron affinities of polycyclic aromatic hydrocarbons determined by the kinetic method.
Chen G and Cooks RG.
Journal of Mass Spectrometry : Jms, 30(8), 1167-1173 (1995)
Pyrene-functionalized ruthenium nanoparticles: novel fluorescence characteristics from intraparticle extended conjugation.
Chen W, et al.
The Journal of Physical Chemistry C, 113(39), 16988-16995 (2009)
Novel fluorescence probe based on pyrene and piperazine; spectral properties in solution and in polymer matrices.
Hrdlovic P et al.
Journal of Photochemistry and Photobiology A: Chemistry, 163(1), 289-296 (2004)
Tracie Perkins Fullove et al.
Toxicology research, 2(3), 193-199 (2014-06-06)
Polycyclic aromatic hydrocarbons (PAHs), a class of mutagenic environmental contaminants, insert toxicity through both metabolic activation and light irradiation. Pyrene, one of the most widely studied PAHs, along with its mono-substituted derivatives, 1-amino, 1-bromo, 1-hydroxy, and 1-nitropyrene, were chosen to
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)

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