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1,8-Dibromonaphthalene

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CAS:17135-74-9
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  • 1,8-Dibromonaphthalene
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  • 2024-01-23
  • CAS:17135-74-9
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  • 1,8-DIBROMONAPHTALENE
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  • 2023-11-29
  • CAS:17135-74-9
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  • 1,8-DIBROMONAPHTALENE
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  • 2023-11-14
  • CAS:17135-74-9
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  • Purity: 99.9%
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1,8-Dibromonaphthalene Basic information
Product Name:1,8-Dibromonaphthalene
Synonyms:1,8-DIBROMONAPHTALENE;1,8-dibroMonaphthalene 1,8-DBN;1,8-dibroMophthalene;1,8-DBN;Naphthalene,1,8-dibromo-;1,8-dibromonaphthylene;1,8-Dibromonaphthalene >;1,8-DibromonaphthaL
CAS:17135-74-9
MF:C10H6Br2
MW:285.96
EINECS:
Product Categories:Dibromonaphthalene;OLED materials,pharm chemical,electronic;intermediate;OLED
Mol File:17135-74-9.mol
1,8-Dibromonaphthalene Structure
1,8-Dibromonaphthalene Chemical Properties
Melting point 108.0 to 112.0 °C
Boiling point 140°C/0.1mmHg(lit.)
density 1.834±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility soluble in Toluene
form powder or crystals
color White to Yellow to Green
InChIKeyDLXBGTIGAIESIG-UHFFFAOYSA-N
Safety Information
Hazard Codes Xn,N
Risk Statements 22-50
Safety Statements 61
RIDADR UN 3077 9 / PGIII
WGK Germany 3
HS Code 29039990
MSDS Information
1,8-Dibromonaphthalene Usage And Synthesis
Chemical PropertiesWhite to yellow powder/crystals.
Application1,8-Diarylnaphthalene 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.
Preparation1,8-dibromonaphthalene was prepared by diazotisation of triazine 1 with sodium nitrite in sulfuric acid, followed by the addition of CuBr/HBr in 44% yield, and cyanation of the dibromide (5) by Weissman’s method gave naphthalene-1,8-dicarbonitrile (4) in 78% yield (Scheme 2).
Synthesis of 1,8-dibromonaphthalene
ReactionsInfluence of the conditions on the Pd-catalyzed reaction of 1,8-dibromonaphthalene with 1,2,3,4-tetrafluorobenzene.

Scope of the Pd-catalyzed direct arylation reaction of 2,5-substituted heteroarenes with 1,8-dibromonaphthalene.
Structure and conformation1,8-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.
References[1] W. NOLAND D. B Venkata Srinivasarao Narina. Synthesis and Crystallography of 8-Halonaphthalene-1-Carbonitriles and Naphthalene-1,8-Dicarbonitrile[J]. Journal of Chemical Research-s, 2011, 383 1: 694-697. DOI:10.3184/174751911X13222107572093.
[2] PROF. DR. ANNA V. GULEVSKAYA Eugeny A E. 1,8‐Diarylnaphthalenes: Synthesis, Properties, and Applications[J]. European Journal of Organic Chemistry, 2022, 2022 48: Pages 53-111. DOI:10.1002/ejoc.202201192.
[3] KETATA N, LIU L, SALEM R B, et al. Mono or double Pd-catalyzed C–H bond functionalization for the annulative π-extension of 1,8-dibromonaphthalene: a one pot access to fluoranthene derivatives[J]. Beilstein Journal of Organic Chemistry, 2024, 16 1. DOI:10.3762/bjoc.20.37.
1,8-Dibromonaphthalene Preparation Products And Raw materials
Raw materials1,8-Diaminonaphthalene-->1H-NAPHTHO[1,8-DE][1,2,3]TRIAZINE
Preparation Products1,8-DICHLORONAPHTHALENE-->1-BROMO-8-METHYLNAPHTHALENE-->1-Naphthaleneethanol, 8-bromo-
Tag:1,8-Dibromonaphthalene(17135-74-9) Related Product Information
4,5-DIBROMO-1,8-NAPHTHALENEDICARBOXYLIC ACID hexabromonaphthalene 5,6-DIBROMOACENAPHTHENE 1,3,9,10-TETRABROMO-ANTHRACENE 1,4,9,10-TETRABROMO-ANTHRACENE 1,8-DIBROMONAPHTALENE