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Product Code B1271-10g
Price £120 ex. VAT

A well known double brominated naphthalene intermediate

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

Specifications | MSDS | Literature and Reviews

1,8-Dibromonaphthalene (1,8-DBN), CAS number 17135-74-9, 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.
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