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Product Code B1251-1g
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Dihalogenated naphthalene compound can be a suitable host for fluorescent polycyclic aromatic hydrocarbons molecules

Also used as a building block leading to more complex structures in application of organic electronics.


2,3-Dibromonaphthalene (2,3-DBN), CAS number 13214-70-5, is another useful intermediate and isomer of dibromonaphthalene with two heavy bromo substituents sitting next to each other around the naphthalene ring.

X-ray diffraction analysis shows that the crystal structure of 2,3-dibromonaphthalene is ordered where the weak and directional forces generate the herringbone packing of the constituting molecules. For this reason, 2,3-dibromonaphthalene is employed as a suitable host for fluorescent  polycyclic aromatic hydrocarbons (PAH) molecules. Single molecules of terrylene in 2,3-dibromonaphthalene crystallise also in a herringbone pattern, directed by the 2,3-dibromonaphthalene host.

General Information

CAS Number 13214-70-5
Chemical Formula C10H6Br2
Full Name 2,3-Dibromonaphthalene
Molecular Weight 285.97 g/mol
Synonyms 2,3-DBN
Classification / Family Naphthalenes, Semiconductor synthesis intermediates, Low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

2,3-dibromonaphthalene chemical structure, 13214-70-5
2,3-Dibromonaphthalene (2,3-DBN) chemical structure, CAS 13214-70-5

Product Details

Purity >98% (1H NMR)
Melting Point Tm = 142 °C
Appearance White to off-white powder/crystals

MSDS Documentation

2,3-Dibromonaphthalene2,3-Dibromonaphthalene MSDS Sheet

Literature and Reviews

  1. A Highly Warped Heptagon-Containing sp2 Carbon Scaffold via Vinylnaphthyl π-Extension, J. Farrell et al., Angew.Chem., 131, 16656–16659 (2019); DOI:10.1002/ange.201909975.
  2. Matrix-induced Linear Stark Effect of Single Dibenzoterrylene Molecules in 2,3-Dibromonaphthalene Crystal, A. Moradi et al., ChemPhysChem, 20,55–61 (2019); DOI: 10.1002/cphc.201800937.
  3. Spectra and nature of the electronic excited states of 2,3-dibromonaphthalene single crystals, I. Deperasińska et al., J. Lumin., 213, 108-116 (2019); DOI: 10.1016/j.jlumin.2019.05.011.
  4. A convenient generation of 2,3-naphthalyne. Linear annulation of naphthalene and a new naphthacene synthesis, C. LeHoullier et al., J. Org. Chem., 48, 14, 2364–2366 (1983); DOI: 10.1021/jo00162a013.
  5. Synthesis of 2,3-dialkyl-6,7-dichloro- and 2,3-dialkyl-6,7-dibromo-1,4-naphthoquinones, A. Ashnagar et al., J. Chem. Soc., Perkin Trans., 1, 559-561 (1988); DOI: 10.1039/P19880000559.
  6. Synthesis of tetraaryl-p-benzoquinones and 2,3-diaryl-1,4-naphthoquinones via Suzuki–Miyaura cross-coupling reactions, Z. Hassan et al., Tetrahedron, 69 (2), 460-469 (2013); DOI: 10.1016/j.tet.2012.11.040.
  7. Synthesis of Substituted Dibenz[a,c]anthracenes and an Investigation of Their Liquid-Crystalline Properties, K. Psutka et al., Eur. J. Org. Chem., 2015 (7), 1456-1463 (2015); DOI: 10.1002/ejoc.201403504.
  8. Single organic molecules for photonic quantum technologies, C. Toninelli et al., Nat. Mater. 20, 1615–1628 (2021); DOI: 10.1038/s41563-021-00987-4.
  9. Laser-Induced Frequency Tuning of Fourier-Limited Single-Molecule Emitters, M. Colautti et al., ACS Nano, 14, 10, 13584–13592 (2020); DOI: 10.1021/acsnano.0c05620.
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