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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

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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Electrosynthesis of blue-light-emitting oligo (1-bromopyrene) with favorable solubility.
Wang, Zhen, et al.
Journal of Solid State Electrochemistry, 16(5), 1907-1915 (2012)
Synthesis of bipyridine and terpyridine based ruthenium metallosynthons for grafting of multiple pyrene auxiliaries.
Goze C, et al.
Tetrahedron Letters, 44(48), 8713-8716 (2003)
Kinetic analysis of the reactions of 1-substituted pyrene cation radicals with water in acetonitrile.
Oyama M and Matsui J.
Journal of Electroanalytical Chemistry, 570(1), 77-82 (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
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)

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