ChemicalBook > CAS DataBase List > 1,8-Dibromonaphthalene

1,8-Dibromonaphthalene

Product Name: 1,8-Dibromonaphthalene
CAS No.: 17135-74-9
Chemical Name: 1,8-Dibromonaphthalene
Synonyms: CASC;1,8-DBN;1,8-dibromonalene;8-DIBROMONAPHTALENE;1,8-DibromonaphthaL;1,8-dibroMophthalene;1,8-DIBROMONAPHTALENE;1,8-dibromonaphthylene;1,8-dibromonaphthalene;Naphthalene,1,8-dibromo-
CBNumber: CB7303678
Molecular Formula: C10H6Br2
Formula Weight: 285.96
MOL File: 17135-74-9.mol

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1,8-Dibromonaphthalene Property

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
InChI: InChI=1S/C10H6Br2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H
InChIKey: DLXBGTIGAIESIG-UHFFFAOYSA-N
SMILES: C1(Br)=C2C(C=CC=C2Br)=CC=C1

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Safety

Hazard Codes: Xn,N
Risk Statements: 22-50
Safety Statements: 61
RIDADR: UN 3077 9 / PGIII
WGK Germany: 3
HazardClass: 9
HS Code: 29039990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 764094
Product name: 1,8-Dibromonaphthalene
Purity: 97%
Packaging: 1g
Price: $99.6
Updated: 2025/07/31

TCI Chemical

Product number: D4656
Product name: 1,8-Dibromonaphthalene
Purity: >98.0%(GC)
Packaging: 1g
Price: $54
Updated: 2025/07/31

TCI Chemical

Product number: D4656
Product name: 1,8-Dibromonaphthalene
Purity: >98.0%(GC)
Packaging: 5g
Price: $156
Updated: 2025/07/31

TRC

Product number: D426273
Product name: 1,8-Dibromonaphthalene
Packaging: 50mg
Price: $60
Updated: 2021/12/16

Oakwood

Product number: 214784
Product name: 1,8-Dibromonaphthalene
Packaging: 5g
Price: $59
Updated: 2021/12/16

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1,8-Dibromonaphthalene Chemical Properties,Usage,Production

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.

Synthesis

204-03-5

17135-74-9

The general procedure for the synthesis of 1,8-dibromonaphthalene from 1H-naphtho[1,8-de][1,2,3]triazine was as follows: solid sodium nitrite (NaNO2, 3.5 g, 0.05 mol) was dissolved in 20 mL of water and cooled down to 0 °C. The sodium nitrite solution was added dropwise to a solution of 1H-naphtho[1,8-de][1,2,3]triazine (6.8 g, 0.04 mol) dissolved in 6.9 M sulfuric acid (H2SO4, 100 mL) at -5 °C. The reaction mixture was stirred vigorously with a mechanical stirrer at -5°C for 2 hours, followed by continued stirring at the same temperature for 2 hours. Next, a solution of cuprous bromide (CuBr, 14.6 g, 0.1 mol) dissolved in 47% aqueous hydrobromic acid (HBr, 50 mL) was added dropwise to the above mixture and stirred for 2 hours at -5°C. The reaction mixture was gradually warmed to 85°C and stirring was continued for 1 hour. Upon completion of the reaction, the reaction mixture was extracted with dichloromethane, the organic phases were combined and dried over anhydrous sodium sulfate (Na2SO4). Subsequently, the solvent was removed by vacuum evaporation to give the crude product. The crude product was purified by silica gel column chromatography using petroleum ether as eluent to afford pure 1,8-dibromonaphthalene (2.61 g, 23% yield) as light yellow crystals. The melting point of the product was 104-106 °C. 1H NMR (300 MHz, CDCl3): δ 7.92 (d, J = 7.5 Hz, 2H), 7.79 (d, J = 9.0 Hz, 2H), 7.24 (m, 2H).

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 1,8-Dibromonaphthalene manufacturers

Hebei Chuanghai Biotechnology Co., Ltd

Product: 1,8-DIBROMONAPHTALENE 17135-74-9
Price: US $30.00-10.00/KG
Min. Order: 50KG
Purity: 99%
Supply Ability: 500000kg
Release date: 2024-10-24

Shanghai Daken Advanced Materials Co.,Ltd

Product: 1,8-Dibromonaphthalene 17135-74-9
Price: US $0.00/KG
Min. Order: 1KG
Purity: 98.00%
Supply Ability: 150KG /month
Release date: 2021-11-18

Hebei Yanxi Chemical Co., Ltd.

Product: 1,8-DIBROMONAPHTALENE 17135-74-9
Price: US $0.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 20 tons
Release date: 2023-11-29

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intermediate

OLED