| Identification | More | [Name]
2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE | [CAS]
84-59-3 | [Synonyms]
1,5-DIHYDROXY-2,6-DIBROMONAPHTHALENE
2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE
2,6-DIBROMO-1,5-NAPHTHALENEDIOL
2,6-dibromo-5-naphthalenediol
2,6-dibromonaphthalene-1,5-diol | [EINECS(EC#)]
201-543-8 | [Molecular Formula]
C10H6Br2O2 | [MDL Number]
MFCD00021473 | [Molecular Weight]
317.96 | [MOL File]
84-59-3.mol |
| Safety Data | Back Directory | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [HS Code ]
2908.19.6000 |
| Hazard Information | Back Directory | [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]
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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Energy Chemical
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