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

InChIKey

DLXBGTIGAIESIG-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

1,8-Dibromonaphthalene Usage And Synthesis

Chemical Properties

White to yellow powder/crystals.

Application

1,8-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.

Preparation

1,8-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).

Reactions

Influence 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 conformation

1,8-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(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