2,7-Dibromonaphthalene

CAS Number 58556-75-5

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

A double brominated naphthalene intermediate

Used for the construction of molecules in application of optical memory transistors, air pollution and organic electronic devices.

Specifications | MSDS | Literature and Reviews

2,7-Dibromonaphthalene (2,7-DBN), CAS number 58556-75-5, is one of many double brominated naphthalenes that has a symmetrical structure along the the joining carbons. It has been used as an intermediate for constructing semiconducting molecules in application of OLEDs and OFETs, and polymers for OPVs and air pollution applications.

Organic semiconductor of 2,7-di(anthracen-2-yl)naphthalene, with a naphthalene and two anthracene pendants at 2,7-positions , exhibits excellent hole-transport mobility of 3.3 cm² V^-1 s^-1. It also shows a high photoresponsivity of 8000 A W^-1 with detectivity as high as 1.2 × 10¹⁴ Jones [1]. Apart from that, different from traditional strategies towards memory devices, optical memory transistors (OMTs) based on 2,7-di(anthracen-2-yl)naphthalene display an excellent memory effect due to the inhomogeneity of the film only.

Nanotube air filters based on conjugated microporous polymers (CMPs) block type aerogel which are derived from 2,7-dibromonaphthalene are used in the purification of dusty air. The filters can take up to 172.73 wt% gaseous iodine and exhibit their potential as bifunctional filtration materials for capturing both particulate matter (PM) and volatile substances [2].

Naphthalene building block

for the synthesis of OLED and organic photovoltaic materials

Worldwide shipping

Quick and reliable shipping

Capped with bromides

for facile coupling reactions

High purity

>98% Purity

General Information

CAS Number	58556-75-5
Chemical Formula	C₁₀H₆Br₂
Full Name	2,7-Dibromonaphthalene
Molecular Weight	285.97 g/mol
Synonyms	2,7-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 = 141 °C
Appearance	White to off-white powder/crystals

MSDS Documentation

2,7-Dibromonaphthalene MSDS Sheet

Literature and Reviews

High-performance optical memory transistors based on a novel organic semiconductor with nanosprouts, L. Zheng et al., Nanoscale, 11, 7117-7122 (2019); DOI: 10.1039/C9NR00578A.
Bifunctional conjugated microporous polymer based filters for highly efficient PM and gaseous iodine capture, Z. Tian et al., Polym. Chem., 13, 3681-3688 (2022); DOI: 10.1039/D2PY00529H.
Highly heat-resistant branched silicon-containing arylacetylene resins with low curing temperature, Z. Ling et al., Polym. Int., 70, 1595–1603 (2021); DOI: 10.1002/pi.6254.

Synthesis of Highly Twisted, Nonplanar Aromatic Macrocycles Enabled by an Axially Chiral 4,5-Diphenylphenanthrene Building Block, Y. Li et al., J. Am. Chem. Soc., 142 (6), 3246–3253 (2020); DOI: 10.1021/jacs.9b13549.
Dual Association Modes of the 2,5,8-Tris(pentafluorophenyl)phenalenyl Radical, K. Uchida et al., Chem. Asian J., 9 (7), 1823-1829 (2014); DOI: 10.1002/asia.201402187.
[n]Cyclo-2,7-naphthylenes: Synthesis and Isolation of Macrocyclic Aromatic Hydrocarbons having Bipolar Carrier Transport Ability, Angew. Chem. Int. Ed., 50 (23), 5323-5326 (2011); DOI: 10.1002/anie.201101314.
2,7-Dibromonaphthalene and 4,4′-dibromobiphenyl in the synthesis of oxadiamine N, N, N′, N′-tetraaryl derivatives and studies of formation of bismacrocyclic compounds from them, A. Averin et al., Russ. Chem. Bull. 70, 2164–2179 (2021); DOI: 10.1007/s11172-021-3328-7.
Synthesis of Macrocycles Comprising 2,7-Disubstituted Naphthalene and Polyamine Moieties via Pd-catalyzed Amination, A. Averin et al., Chem. Lett., 37 (10), 1074-1075 (2008); DOI: 10.1246/cl.2008.1074.