13214-70-5

Basic information

• Product Name: 2,3-DIBROMONAPHTHALENE
• Synonyms: 2,3-DIBROMONAPHTHALENE;Naphthalene, 2,3-dibromo-;2,3-BibroMonaphthalene;2,3-DIBROMOPHTHALENE
• CAS NO: 13214-70-5
• Molecular Formula: C₁₀H₆Br₂
• Molecular Weight: 285.96
• Product Categories: Dibromonaphthalene
• Mol File: 13214-70-5.mol

Chemical Properties

• Melting Point: 140.0 to 144.0 °C
• Boiling Point: 288.1°C (rough estimate)
• Flash Point: 186.6 ºC
• Appearance: /
• Density: 1.8199 (estimate)
• Vapor Pressure: 0.000156mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 136.6ug/L(25 oC)
• CAS DataBase Reference: 2,3-DIBROMONAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIBROMONAPHTHALENE(13214-70-5)
• EPA Substance Registry System: 2,3-DIBROMONAPHTHALENE(13214-70-5)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 13214-70-5(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C10H6Br2/c11-9-5-7-3-1-2-4-8(7)6-10(9)12/h1-6H

Upstream product

• 91-20-3 naphthalene 
• 4453-90-1 1,4-dihydro-1,4-methanonaphthalene 
• 22193-62-0 (1RS,2RS,5RS)-2,3,3-dibromo-6,7-benzobicyclo<3.2.1>octa-3,6-diene 
• 117269-34-8 2,3-Dibromo-5,6-benzotricyclo<2.2.2>octa-2,5,7-triene 
• 106750-88-3 4,5-dibromo-11-oxatricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5,9-tetraene 
• 5696-92-4 1,2,3,4,5,6,7,8,13,13,14,14-dodecachloro-1,4,4a,4b,5,8,8a,12b-octahydro-1,4;5,8dimethano-triphenylene 
• 107784-15-6 (3-bromo-[2]naphthyl)-carbamic acid ethyl ester 
• 690244-08-7 1,3-dibromo-2-nitro-naphthalene 
• 80789-65-7 10-bromo-1,2,3,4,5,6,7,8,13,13,14,14-dodecachloro-1,4,4a,4b,5,8,8a,12b-octahydro-1,4;5,8-dimethanotriphenylene 
• 106-37-6 1.4-dibromobenzene 
• 636-28-2 1,2,4,5-tetrabromobenzene 
• 73392-23-1 1,2-bis(trimethylsilylethynyl)benzene 
• 256439-90-4 1,2-bis(bromoethynyl)benzene 
• 67102-98-1 10,11-dibromo-1,2,3,4,5,6,7,8,13,13,14,14-dodecachloro-1,4,4a,4b,5,8,8a,12b-octahydro-1,4;5,8-dimethanotriphenylene 

Downstream Products

• 92-24-0 Tetracen 
• 1259947-73-3 6,13-diphenylpentaleno[1,2-b:4,5-b']dinaphthalene 
• 258-47-9 Dibenzo[b,h]biphenylene 
• 99643-51-3 2,3-bis(benzylthio)naphthalene 
• 131354-68-2 2,2'-(2,3-Naphthylenedioxy)diphenol bis(methyl ether) 
• 54245-34-0 3-Brom-2-Naphthonitril 
• 226-97-1 dibenzo[b,h]acridine 
• 257-89-6 benz[b]acridine 
• 22187-13-9 1,4-dihydro-1,4-epoxyanthracene 
• 258-38-8 heptacene 

Relevant articles and documents

Synthesis of substituted dibenz[a,c]anthracenes and an investigation of their liquid-crystalline properties

We report the synthesis of a series of 2,3,5,6-tetraalkoxydibenz[ a,c]anthracenes bearing substituents (H, OCH3, or CN) in the 11- and 12-positions and an investigation of their liquid- crystalline properties. The synthesis involved Suzuki coupling of the appropriate dibromonaphthalene and boronate ester, followed by an oxidative cyclization. Compounds 4 and 5, bearing OCH3 and H, respectively, do not exhibit any liquid-crystalline properties. In contrast, compounds 6a-c, bearing cyano groups, assemble into columnar mesophases, suggesting that electron-withdrawing groups are important for promoting columnar mesophase assembly. Analysis of the XRD revealed that compound 6b exhibits a columnar hexagonal phase, whereas compounds 6a and 6c exhibit columnar rectangular phases. The XRD data of 6a and 6b also show reflections that are consistent with antiparallel dimers within the columnar stacks, and intercolumnar spacings suggest that molecules are tilted within the columns.

The photochemical synthesis of naphtho[2,3-g]thiopheno[3,2- e]benzo[b]thiophene: A new heterocyclic system

The synthesis is described of the hitherto unknown 2,3-bis(2'- thienyl)naphthalene (1). Photochemical cyclisation of 1 affords naphtho[2,3- g]thiopheno[3,2-e]benzo[b]thiophene (2), the parent compound of a new aromatic heterocyclic series.

Selective Vicinal Diiodination of Polycyclic Aromatic Hydrocarbons

Vicinally diiodinated polycyclic aromatic hydrocarbons (I2-PAHs) are accessible from the corresponding diborylated B2-PAHs through boron/iodine exchange. The B2-PAHs have been prepared via twofold electrophilic borylation reactions templated by a vicinally disilylated benzene. Our protocol is applicable to fluorenes, acenes, annulated acenes, oligoaryls, and even [5]helicene. Using B2-naphthalene as the example, we have shown that the reaction scope can, in principle, be expanded to include the synthesis of vicinally dibrominated and dihydroxylated PAHs. The usefulness of the building blocks provided by our method in the field of optoelectronic materials was demonstrated by the successful conversion of I2-fluoranthene to the analogous doubly alkynylated fluoranthene emitter.

Regioselective arene homologation through rhenium-catalyzed deoxygenative aromatization of 7-oxabicyclo[2.2.1]hepta-2,5-dienes

Combined use of oxorhenium catalysts with triphenyl phosphite as an oxygen acceptor allowed efficient deoxygenative aromatization of oxabicyclic dienes. The reaction proceeded under neutral conditions and was compatible with various functional groups. Combining this deoxygenation with regioselective bromination and trapping of the generated aryne with furan resulted in benzannulative π-extension at the periphery of the PAHs. This enabled direct use of unfunctionalized PAHs for extension of π-conjugation. Iteration of the transformations increased the number of fused-benzene rings one at a time, which has the potential to alter the properties of PAHs by fine-tuning the degree of π-conjugation, shape, and edge topology.

How Boron Doping Shapes the Optoelectronic Properties of Canonical and Phenylene-Containing Oligoacenes: A Combined Experimental and Theoretical Investigation

Optimized syntheses of 6,13-dimesityl-6,13-dihydro-6,13-diborapentacene (DBP) and a related compound (DBI) featuring two biphenylene-2,3-diyl units in place of naphthalene-2,3-diyl moieties are reported. Striking differences between the optoelectronic properties of DBP and DBI have been experimentally observed, and explained by quantum chemical calculations. DBP is a member of the oligoacene family, DBI is a linear [N]phenylene derivative. The yellow DBP shows blue photoluminescence, the deep red DBI is nonfluorescent. Both compounds give rise to two reversible redox transitions at E12 =?2.03 V, ?2.75 V (DBP) and ?1.52 V, ?2.30 V (DBI; THF, vs. FcH/FcH+). The higher electron affinity of DBI agrees with a lower calculated LUMO energy level [?0.57 eV for DBI with respect to DBP @HF//SCS-MP2/def2-TZVP] and a higher Lewis acidity of its boron centers, which is reflected in the trend of adduct formation with small Lewis bases (MeCN, F?). The thermochemistry underlying this trend, as well as the mechanism of fluorescence quenching in DBI, are revealed by state-of-the-art quantum chemical calculations. It is suggested that the nonradiative deactivation occurs via a low-lying, doubly excited state.

Access to polysubstituted naphthalenes and anthracenes via a retro-Diels–Alder reaction

Naphthalene and anthracene nuclei are present in several natural and synthetic compounds. Due to their unique physical and chemical properties, access to functionalized naphthalenes and anthracenes has attracted the attention of both synthetic and medicinal chemists over the decades. In this study, successive Diels–Alder/retro-Diels–Alder reactions of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with various bicyclic alkenes in one pot to yield naphthalene and anthracene derivatives are reported. Using anti- and syn-cyclotrimers derived from the cyclotrimerization of benzobarrelene as alkene partner enabled efficient synthesis of trinaphthylene.

MULTICYCLIC AROMATIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME

The present specification describes a multicyclic aromatic ring compound having a novel structure and an organic light emitting device using the same.

Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organomagnesium Reagents

A direct transformation of carboxylic acid esters into arenes with 1,5-bifunctional organomagnesium reagents is described. This efficient and practical method enables the one-step defunctionalization of various carboxylic acid esters to prepare benzene, anthracene, tetracene, and pentacene derivatives. A double nucleophilic addition of the 1,5-organodimagnesium reagent to the ester is followed by an immediate 1,4-elimination reaction that leads to the direct [5+1] formation of a new aromatic ring.

Synthesis of hydroxy, epoxy, nitrato and methoxy derivatives of tetralins and naphthalenes

Stereoselective syntheses are described for cis,trans,cis-2,3,5-tribromo-1, 4-dihydroxytetralin, trans,trans,cis-2,3,5-tribromo-1,4-dihydroxytetralin, trans,trans,trans-1,4-dihydroxy-2,3-dibromotetralin, trans,trans,trans-1- hydroxy-2,3,4-tribromotetralin, cis,cis,cis-1,2-epoxy-3,5-dibromo-4- hydroxytetralin, anti-1,2:3,4-diepoxytetralin, 1-hydroxy-4-bromonaphthalene, trans,trans,trans-1,4-dinitrato-2,3-dibromotetralin, 1-nitrato-2,3,4- tribromotetralin, 2,3-dibromonaphthalene and 1-methoxy-4-nitrato-2,3- dibromonaphthalene. These isomeric arene oxides and disubstituted naphthalenes provide excellent precursors for a number of 1,4- and 2,3-disubstituted naphthalene derivatives that are difficult to prepare using other routes. The structures of the naphthalene and tetralin derivatives were assigned by NMR and other techniques.

The metalation of 1- and 2-(trifluoromethyl)naphthalenes: Noteworthy site selectivities

This article provides insight into the various factors by which electronegative substituents affect the kinetic acidity of arenes and, more specifically, naphthalenes. Both 1- and 2-(trifluoromethyl)naphthalenes were consecutively treated with an organometallic or lithium dialkylamide-type base and carbon dioxide. Due to single electron-transfer triggered side reactions, the yields of (trifluoromethyl)naphthoic acids were moderate to poor. 1-(Trifluoromethyl)naphthalene was exclusively attacked at the 2-position as expected. The 2-isomer reacted with tert-butyllithium in the presence of potassium tert-butoxide solely at the 1-position, but with sec-butyllithium in the presence of N,N,N′,N′-tetramethylethylene-diamine concomitantly at the 3- and 4-positions. Authentic samples of the key acids 1, 4, 5 and 6 were prepared based on independent, unambiguous methods.