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Product Code B1201-50g
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A well known intermediate used for the synthesis of functional materials

Used for drug discoveries, coordination chemistry and organic electronic devices.

1,4-Dibromonaphthalene (1,4-DBN) is a bis-brominated naphthalene at 1,4-positions. 1,4-dibromonaphthalene can be obtained by the treatment of 1-bromonaphthalene with bromine in dichloromethane at -30 °C in high yield.

1,4-Dibromonaphthalene is well known as a triplet excitation acceptor with useful phosphorescent properties. It is also an useful intermediate for the synthesis of other 1,4-dibromonaphthalene derivatives in drug discovery such as enzyme-inhibitory, antifungal, antibacterial, anticancer, anti-inflammatory, antiallergic, phenols, amines,  coordination chemistry and organic electronic devices. Ambipolar deep-blue emitter, 4,4′-bis(4-(1-(4-(tert-butyl)phenyl)-1H-phenanthro[9,10-d]imidazol-2-yl)phenyl)-1,1′-binaphthalene (2NBTPI), derived from 1,4-dibromonaphthalene, demonstrates spatially separated HOMO and LUMO orbits, a high thermal stability and deep blue emission in OLED device.

General Information

CAS Number 83-53-4
Chemical Formula C10H6Br2
Full Name 1,4-Dibromonaphthalene
Molecular Weight 285.97 g/mol
Synonyms 1,4-DBN
Classification / Family Naphthalenes, Semiconductor synthesis intermediates, Low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

1,4-Dibromonaphthalene, CAS 83-53-4
1,4-Dibromonaphthalene (1,4-DBN) chemical structure, CAS 83-53-4

Product Details

Purity >98% (1H NMR)
Melting Point Tm = 82 °C
Appearance White to off-white powder/crystals

MSDS Documentation

1,4-Dibromonaphthalene1,4-Dibromonaphthalene MSDS Sheet

Literature and Reviews

  1. Highly efficient desymmetrisation of a tricarbonylchromium 1,4-dibromonaphthalene complex by asymmetric Suzuki–Miyaura coupling, X. Urbaneja et al., Chem. Commun., 47, 3739-3741 (2011); DOI: 10.1039/C1CC10347D.
  2. An environment-friendly method for synthesis of 1,4-dibromo-naphthalene in aqueous solution of ionic liquids, X. Zhao et al., Catal. Commun., 9(13), 2179-2182 (2008); DOI:10.1016/j.catcom.2008.04.020.
  3. Intrachain and interchain triplet-triplet exciton annihilation in a quasi-one-dimensional crystal: 1,4-dibromonaphthalene (DBN), H. Bouchriha et al., Chem. Phys. Lett., 53 (2), 288-293 (1978); DOI: 10.1016/0009-2614(78)85398-6.
  4. Triplet-triplet interaction in a nearly one dimensional molecular crystal: Application to 1,4-dibromonaphtalene, A. Benfredj et al., Eur. Phys. J. B 19, 385–391 (2001); DOI: 10.1007/s100510170314.
  5. A novel chemical approach for synthesizing highly porous graphene analogue and its composite with Ag nanoparticles for efficient electrochemical oxygen reduction, A. Das et al., Chem. Eng. J., 451 (3), 138766 (2023); DOI: 10.1016/j.cej.2022.138766.
  6. An efficient solution-processable hybridized local and charge-transfer (HLCT)-based deep-red fluorescent emitter for simple structured non-doped OLED, S. Kongsabay et al., J. Lumin., 248, 118921 (2022); DOI: 10.1016/j.jlumin.2022.118921.
  7. Molecular modification on bisphenanthroimidazole derivative for deep-blue organic electroluminescent material with ambipolar property and high performance, Org. Electron., 17, 159-166 (2015); DOI: 10.1016/j.orgel.2014.11.024.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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