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
- Molecular Weight:
- 285.96
- MDL Number:
- MFCD00183574
- MOL File:
- 17135-74-9.mol
- MSDS File:
- SDS
| Product description | Number | Pack Size | Price |
| 1,8-Dibromonaphthalene 97% | 764094 | 1g | $106 |
| 1,8-Dibromonaphthalene >98.0%(GC) | D4656 | 1g | $46 |
| 1,8-Dibromonaphthalene >98.0%(GC) | D4656 | 5g | $133 |
| 1,8-Dibromonaphthalene | D426273 | 50mg | $60 |
| 1,8-Dibromonaphthalene | 214784 | 5g | $59 |
| More product size | |||
| 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 |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS09 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302-H411 |
| Precautionary statements | P273-P301+P312+P330 |
| Hazard Codes | Xn,N |
| Risk Statements | 22-50 |
| Safety Statements | 61 |
| RIDADR | UN 3077 9 / PGIII |
| WGK Germany | 3 |
| HazardClass | 9 |
| HS Code | 29039990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Chronic 2 |
| Limited Quantities | 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid) |
| Excepted Quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
1,8-Dibromonaphthalene price More Price(40)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 764094 | 1,8-Dibromonaphthalene 97% | 17135-74-9 | 1g | $106 | 2026-04-30 | Buy |
| TCI Chemical | D4656 | 1,8-Dibromonaphthalene >98.0%(GC) | 17135-74-9 | 1g | $46 | 2026-04-30 | Buy |
| TCI Chemical | D4656 | 1,8-Dibromonaphthalene >98.0%(GC) | 17135-74-9 | 5g | $133 | 2026-04-30 | Buy |
| TRC | D426273 | 1,8-Dibromonaphthalene | 17135-74-9 | 50mg | $60 | 2021-12-16 | Buy |
| Oakwood | 214784 | 1,8-Dibromonaphthalene | 17135-74-9 | 5g | $59 | 2021-12-16 | Buy |
1,8-Dibromonaphthalene Chemical Properties,Uses,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
![1H-NAPHTHO[1,8-DE][1,2,3]TRIAZINE](/CAS/GIF/204-03-5.gif)
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
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Yurui (Shanghai) Chemical Co., Ltd. | +86-021-50456736 +8613761615711 | yuki@riyngroup.com | China | 1028 | 58 |
| Baynoe Chem (Suzhou) Co., Ltd. | +86-512 65869404 +86-18934593683 | sales06@baynoe.com | China | 257 | 58 |
| Hebei Yanxi Chemical Co., Ltd. | +8618531123677 | faithe@yan-xi.com | China | 5853 | 58 |
| Hebei Chuanghai Biotechnology Co., Ltd | +8615531151365 | mina@chuanghaibio.com | China | 18126 | 58 |
| Hebei Xinsheng New Material Technology Co., LTD. | +86-16632316109 | xinshengkeji@xsmaterial.com | China | 1085 | 58 |
| Springchem New Material Technology Co.,Limited | +86-021-62885108 +8613917661608 | info@spring-chem.com | China | 2068 | 57 |
| Shanghai Daken Advanced Materials Co.,Ltd | +86-2158073036 | info@dakenam.com | China | 13843 | 58 |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21590 | 55 |
| Nanjing ChemLin Chemical Industry Co., Ltd. | 025-83697070 | product@chemlin.com.cn | CHINA | 3009 | 60 |
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 33024 | 60 |
View Lastest Price from 1,8-Dibromonaphthalene manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
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2025-07-02 | 1,8-Dibromonaphthalene
17135-74-9
|
US $0.00 / KG | 1KG | 98.00% | 150KG /month | Shanghai Daken Advanced Materials Co.,Ltd | |
 |
2025-06-27 | 1,8-DIBROMONAPHTALENE
17135-74-9
|
US $30.00-10.00 / KG | 50KG | 99% | 500000kg | Hebei Chuanghai Biotechnology Co., Ltd | |
 |
2025-06-20 | 1,8-DIBROMONAPHTALENE
17135-74-9
|
US $0.00 / kg | 1kg | 0.99 | 20 tons | Hebei Yanxi Chemical Co., Ltd. |
-
- 1,8-Dibromonaphthalene
17135-74-9
- US $0.00 / KG
- 98.00%
- Shanghai Daken Advanced Materials Co.,Ltd
-
- 1,8-DIBROMONAPHTALENE
17135-74-9
- US $30.00-10.00 / KG
- 99%
- Hebei Chuanghai Biotechnology Co., Ltd
-
- 1,8-DIBROMONAPHTALENE
17135-74-9
- US $0.00 / kg
- 0.99
- Hebei Yanxi Chemical Co., Ltd.
