84-59-3

Basic information

• Product Name: 2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE
• Synonyms: 2,6-dibromo-5-naphthalenediol;2,6-dibromonaphthalene-1,5-diol;2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE;2,6-DIBROMO-1,5-NAPHTHALENEDIOL;1,5-DIHYDROXY-2,6-DIBROMONAPHTHALENE
• CAS NO: 84-59-3
• Molecular Formula: C₁₀H₆Br₂O₂
• Molecular Weight: 317.96
• EINECS: 201-543-8
• Mol File: 84-59-3.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 397.4 °C at 760 mmHg
• Flash Point: 194.2 °C
• Appearance: /
• Density: 2.081 g/cm³
• Vapor Pressure: 6.92E-07mmHg at 25°C
• Refractive Index: 1.766
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.19±0.50(Predicted)
• CAS DataBase Reference: 2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE(84-59-3)
• EPA Substance Registry System: 2,6-DIBROMO-1,5-DIHYDROXYNAPHTHALENE(84-59-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 84-59-3(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C10H6Br2O2/c11-7-3-1-5-6(10(7)14)2-4-8(12)9(5)13/h1-4,13-14H

Upstream product

• 83-56-7 1,5-dihydroxynaphthalene 
• 7726-95-6 bromine 
• 7553-56-2 iodine 
• 64-19-7 acetic acid 

Downstream Products

• 1312573-99-1 C₄₂H₅₀F₂O₄ 
• 1312573-97-9 C₂₆H₁₈F₂O₄ 
• 1312573-95-7 C₄₂H₅₀F₂O₄ 
• 1414857-97-8 C₂₆H₂₀Br₂N₂O₆ 
• 1414857-92-3 C₃₈H₃₀N₂O₂ 

Relevant articles and documents

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Synthesis and characterization of tetraoctyloxy substituted naphthalenophanedienes

Tetraoctyloxy-substituted naphthalenophanedienes were synthesized from tetraoctyloxy-substituted dithia[3.3]naphthalenophanes via sequential benzyne Stevens rearrangement, oxidation, and pyrolysis reactions. Surprisingly, only the pseudo-geminal isomer of tetraoctyloxy-substituted dithia[3.3]naphthalenophane was obtained after cyclization of the corresponding starting materials. The structures of the pseudo-geminal isomers of tetraoctyloxy-substituted dithia[3.3]naphthalenophane and tetraoctyloxy-substituted naphthalenophanediene were fully determined by nuclear magnetic resonance spectroscopy, high resolution mass spectrometry, and X-ray crystallography. The pseudo-geminal and pseudo-meta diastereomers of tetraoctyloxy-substituted naphthalenophanedienes were isolated by multiple fractional recrystallization from hexane at 5 °C. The solid state structure of the pseudo-geminal isomer of tetraoctyloxy-substituted naphthalenophanediene revealed strongly distorted naphthyl rings with high levels of ring strain.

From Colorless to Near-Infrared S-Heteroarene Isomers: Unexpected Cycloaromatization of Cyclopenta[ b]thiopyran Catalyzed by PtCl2

S-heteroarenes containing cyclopenta[b]thiopyran moieties were synthesized via intramolecular ring-expanding cycloisomerization from 1-acetyl-2-thienyl-substituted precursors catalyzed by PtCl2. In comparison to the other two S-heteroarene isomers experiencing common 6-endo and 5-exo cyclization processes, the aromatic cyclopenta[b]thiopyran derivative demonstrates intriguing photophysical and electrochemical properties, such as near-infrared absorption, low oxidation potential, and excellent electrochemical stability. Therefore, this work provides an effective pathway to incorporate cyclopenta[b]thiopyran as building blocks for organic semiconductors with unique properties.

Gas adsorption properties of highly porous metal-organic frameworks containing functionalized naphthalene dicarboxylate linkers

Three functionalized metal-organic frameworks (MOFs), MOF-205-NH2, MOF-205-NO2, and MOF-205-OBn, formulated as Zn4O(BTB)4/3(L), where BTB is benzene-1,3,5-tribenzoate and L is 1-aminonaphthalene-3,7-dicarboxylate (NDC-NH2), 1-nitronaphthalene-3,7-dicarboxylate (NDC-NO2) or 1,5-dibenzyloxy-2,6-naphthalenedicarboxylate (NDC-(OBn)2), were synthesized and their gas (H2, CO2, or CH4) adsorption properties were compared to those of the un-functionalized, parent MOF-205. Ordered structural models for MOF-205 and its derivatives were built based on the crystal structures and were subsequently used for predicting porosity properties. Although the Brunauer-Emmett-Teller (BET) surface areas of the three MOF-205 derivatives were reduced (MOF-205, 4460; MOF-205-NH2, 4330; MOF-205-NO2, 3980; MOF-205-OBn, 3470 m2 g-1), all three derivatives were shown to have enhanced H2 adsorption capacities at 77 K and CO2 uptakes at 253, 273, and 298 K respectively at 1 bar in comparison with MOF-205. The results indicate the following trend in H2 adsorption: MOF-205 2 2 2/N2 (15/85 in v/v) and 2.7 for CO2/CH4 (50/50 in v/v) at 298 K. Despite the large reduction (-22%) in the surface area, MOF-205-OBn displayed comparable total volumetric CO2 (at 48 bar) and CH4 (at 35 bar) storage capacities with those of MOF-205 at 298 K: MOF-205-OBn, 305 (CO2) and 112 (CH4) cm3 cm-3, and for MOF-205, 307 (CO2) and 120 (CH4) cm3 cm-3, respectively.