2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE
- Product Name
- 2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE
- CAS No.
- 84-59-3
- Chemical Name
- 2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE
- Synonyms
- 2,6-dibromo-5-naphthalenediol;2,6-dibromonaphthalene-1,5-diol;2,6-DIBROMO-1,5-NAPHTHALENEDIOL;1,5-Naphthalenediol, 2,6-dibromo-;2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE;1,5-DIHYDROXY-2,6-DIBROMONAPHTHALENE;2,6-Dibromo-1,5-dihydroxynaphthalene>
- CBNumber
- CB3347579
- Molecular Formula
- C10H6Br2O2
- Formula Weight
- 317.96
- MOL File
- 84-59-3.mol
2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE Property
- Boiling point:
- 397.4±37.0 °C(Predicted)
- Density
- 2.081±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- form
- powder to crystal
- pka
- 6.19±0.50(Predicted)
- color
- Light yellow to Amber to Dark green
- CAS DataBase Reference
- 84-59-3(CAS DataBase Reference)
Safety
- Risk Statements
- 36/37/38
- Safety Statements
- 26-36/37/39
- HS Code
- 2908.19.6000
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P233Keep container tightly closed.
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304IF INHALED:
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P312Call a POISON CENTER or doctor/physician if you feel unwell.
P321Specific treatment (see … on this label).
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
P340Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P362Take off contaminated clothing and wash before reuse.
P403Store in a well-ventilated place.
P403+P233Store in a well-ventilated place. Keep container tightly closed.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- S348775
- Product name
- 2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE
- Purity
- Aldrich<sup>CPR</sup>
- Packaging
- 1 unit
- Price
- $185
- Updated
- 2025/07/31
- Product number
- D2593
- Product name
- 2,6-Dibromo-1,5-dihydroxynaphthalene
- Purity
- >93.0%(T)
- Packaging
- 5g
- Price
- $253
- Updated
- 2025/07/31
- Product number
- D2593
- Product name
- 2,6-Dibromo-1,5-dihydroxynaphthalene
- Purity
- >93.0%(T)
- Packaging
- 25g
- Price
- $1010
- Updated
- 2025/07/31
- Product number
- D425665
- Product name
- 2,6-Dibromo-1,5-naphthalenediol
- Packaging
- 5G
- Price
- $155
- Updated
- 2021/12/16
- Product number
- HCH0009451
- Product name
- 1 5-DIHYDROXY-2 6-DIBROMONAPHTHALENE
- Purity
- 95.00%
- Packaging
- 100G
- Price
- $2842.44
- Updated
- 2021/12/16
2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE Chemical Properties,Usage,Production
Uses
2,6-Dibromo-1,5-naphthalenediol is a useful synthetic intermediate. It is used to prepare semiconducting polyphenyls and polythiophenes via microwave-assisted Suzuki and Stille cross-coupling reactions. It is also used to prepare and polymerize adamantane or phenylenevinylene or naphthalenevinylene-containing monomers.
Synthesis
83-56-7
84-59-3
Example 17- Synthesis of 2,6-dibromonaphthalene-1,5-diol: 1,5-dihydroxynaphthalene (115.2 g) was suspended in acetonitrile (800 mL) under nitrogen protection. Subsequently, N,N-dimethylformamide (DMF) solution of N-bromosuccinimide (NBS) (400 mL containing 254 g of NBS) was added slowly and dropwise. The reaction mixture was stirred at room temperature and the reaction progress was monitored by gas chromatography-mass spectrometry (GC-MS). Upon completion of the reaction, the reaction was quenched by the addition of water. The resulting precipitate was collected by filtration and washed with plenty of water to give 2,6-dibromonaphthalene-1,5-diol in 80% yield. Mass spectrometry (electrospray ionization, ESI) analysis resulted in a calculated value (C10H6Br2O2) of 317.9614 and a measured value of 317.9.
References
[1] Journal of Organic Chemistry, 2017, vol. 82, # 15, p. 8234 - 8241
[2] Patent: US2011/224445, 2011, A1. Location in patent: Page/Page column 19
[3] Patent: WO2013/149001, 2013, A2. Location in patent: Paragraph 00139
[4] Tetrahedron Letters, 2017, vol. 58, # 40, p. 3854 - 3858
[5] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 12, p. 3558 - 3567
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