1,8-Dibromonaphthalene

CAS Number 17135-74-9

Chemistry Building Blocks, Materials, Monomers, Non-Heterocyclic Building Blocks

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.

Naphthalene building block

For the synthesis of OLED and organic photovoltaic materials

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Brominated at 1,8 positions

For strained organic molecules

High purity

>98% Purity

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

Product Details

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

MSDS Documentation

1,8-Dibromonaphthalene MSDS Sheet

Literature and Reviews

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.
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.
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.

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.
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.
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.
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.