1,4-Dibromonaphthalene

CAS Number 83-53-4

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

A well known intermediate used for the synthesis of functional materials

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

Specifications | MSDS | Literature and Reviews

1,4-Dibromonaphthalene (1,4-DBN), CAS number 83-53-4, 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.

Naphthalene building block

for the synthesis of OLED and organic photovoltaic materials

Worldwide shipping

Quick and reliable shipping

Brominated at 1,4 positions

for facile reactions

High purity

>98% Purity

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

Product Details

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

MSDS Documentation

1,4-Dibromonaphthalene MSDS Sheet

Literature and Reviews

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.
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.
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.

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.
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.
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.
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.