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Product Code B1271-10g
Price $150 ex. VAT

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A well known double brominated naphthalene intermediate

leads to 1,8-diarylnaphthalenes in application of optoelectronic devices and chiral molecules studies.


1,8-Dibromonaphthalene (1,8-DBN) is a symmetrical double bromo-substituted naphthalene with two bromos sitting at the naphthalene ring mirroring each other along the joining carbons. 1,8-Dibromonaphthalene is the building block for 1,8-diarylnaphthalenes, a fascinating class of strained organic molecules.

1,8-Diarylnaphthalenes are great example of strained organic molecules that have unusual parallel face-to-face arrangement of two peri-aryl rings in close proximity almost perpendicular to the central naphthalene backbone. 1,8-Diarylnaphthalenes show great potential in highly efficient photoluminescent blue and green OLEDs, chiral ligands and sensors, nonlinear optic chromophores, stereo-dynamic switches and other optoelectronic devices.

General Information

CAS Number 17135-74-9
Chemical Formula C10H6Br2
Full Name 1,8-Dibromonaphthalene
Molecular Weight 285.97 g/mol
Synonyms 1,8-DBN
Classification / Family Naphthalenes, Semiconductor synthesis intermediates, Low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

1,8-Dibromonaphthalene chemical structure, CAS 17135-74-9
1,8-Dibromonaphthalene (1,8-DBN) chemical structure, CAS 17135-74-9

Product Details

Purity >98% (1H NMR)
Melting Point Tm = 110 °C
Appearance White to Yellow, Pale Beige to Beige, Pale Brown to Brown powder/crystals

MSDS Documentation

1,8-Dibromonaphthalene1,8-Dibromonaphthalene MSDS Sheet

Literature and Reviews

  1. Synthesis and Stereodynamics of Highly Constrained 1,8-Bis(2,2‘-dialkyl-4,4‘-diquinolyl)naphthalenes, G. Tumambac et al., J. Org. Chem., 69(6), 2048-2055 (2004); DOI: 10.1021/jo035547l.
  2. Atropisomerism of cofacial pyridine rings. Synthesis, proton NMR spectra and conformations of 1,8-di(3′-pyridyl)naphthalene, Tetrahedron, J. Zoltewicz et al., 52 (26), 8703-8706 (1996); DOI: 10.1016/0040-4020(96)00447-4.
  3. Naphthalene-1,8-diylbis(diphenylmethylium) as an Organic Two-Electron Oxidant:  Benzidine Synthesis via Oxidative Self-Coupling of N,N-Dialkylanilines, T. Saitoh et al., J. Org. Chem., 71, 17, 6414–6419 (2006); DOI: 10.1021/jo060662s.
  4. Naphtho[1,8-b,c]phosphete and 1,2-Diphosphaacenaphthene from the Reaction of 1,8-Dilithionaphthalene with RPCl2, T. Mizuta et al., Angew. Chem. Int. Ed. Engl., 41(20), 3897-3898 (2002); DOI: 10.1002/1521-3773(20021018)41:20<3897::AID-ANIE3897>3.0.CO;2-H.
  5. Synthesis of Conformationally Stable 1,8-Diarylnaphthalenes:  Development of New Photoluminescent Sensors for Ion-Selective Recognition, C. Wolf et al., J. Am. Chem. Soc., 125 (35), 10651–10658 (2003); DOI: 10.1021/ja0358145.
  6. Stereoselective Domino Rearrangement peri-Annulation of Cinchona Alkaloid Derivatives with 8-Bromo-1-naphthyl Grignard, P. Boratyński et al., J. Org. Chem., 87, 17, 11602–11607 (2022); DOI: 10.1021/acs.joc.2c01249.
  7. Synthesis and Characterization of Naphtho[2,1-b:7,8-b′]bis[1]-benzothiophene, J. Kaiser et al., Eur. J. Org. Chem., 66–69 (2020); DOI: 10.1002/ejoc.201901299.

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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