cas 83-53-4, 1,4-Dibromonaphthalene | Articles data

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Bayer,O'Reilly
p. 311
(1958)
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Oxygen-Doped PAH Electrochromes: Difurano, Dipyrano, and Furano-Pyrano Containing Naphthalene-Cored Molecules
In this work, we report the synthesis of O-doped naphthalene-based electrochromes. Exploiting the CuO-mediated Pummerer oxidative cycloetherification reaction, a series of 1,4- and 1,5-disubstituted naphthalene-cored dipyrano, difurano, and furano-pyrano polycyclic aromatic hydrocarbons (PAHs) have been prepared. Steady-state UV-Vis absorption and emission investigations showed that the spectroscopic profile strongly depends on the O-doping topology, with the dipyrano and the difurano derivatives demonstrating the most red-shifted and blue-shifted electronic transition, respectively. Computational investigations revealed that the cycloetherification reaction raises the HOMO energy level (while the LUMO remains largely unaffected), with the dipyrano derivatives displaying the highest values. Spectroelectrochemical measurements showed that, depending on the O-topology and the type of O-ring, different electrochromic responses could be obtained with colour transitions featuring high contrasts involving yellow, pink, orange or blue colours.
Abraham, Michael,Bonifazi, Davide,Ferreira, Rúben R.,Fletcher-Charles, Jack,González, Leticia,Oppel, Markus,Romito, Deborah
(2021/11/23)

Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides
A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.
Nishii, Yuji,Ikeda, Mitsuhiro,Hayashi, Yoshihiro,Kawauchi, Susumu,Miura, Masahiro
supporting information
p. 1621 - 1629
(2020/02/04)

Preparation method of high-purity 1,4-dibromonaphthalene
The invention relates to a preparation method of high-purity 1,4-dibromonaphthalene and belongs to the technical field of organic synthesis. The provided preparation method of high-purity 1,4-dibromonaphthalene aims to solve the problems that preparation methods of 1,4-dibromonaphthalene in the prior art are complicated, the reaction conditions are high, the product purity is low, the yield is low, and the product quality is unstable. The method comprises the four steps of a one-pot acetylation protection and selective bromination process, a hydrolysis deprotection process, a diazotization coupling reaction process and a recrystallization purification process to obtain high-purity 1,4-dibromonaphthalene. The provided preparation method has the advantages that the synthesis route is short,the reaction conditions are mild and easy to control, and the production cost is low. The organic synthesis reaction site is monotonous, the selectivity is high, the product purity is up to 99.0%, andthe total yield can reach 71.7%. Industrial production is easily realized, the need for large-scale production of 1,4-dibromonaphthalene can be effectively met, and the method has a broad applicationprospect.
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(2019/10/01)

PROCESS FOR PRODUCING 1,5-DIBROMONAPHTHALENE
PROBLEM TO BE SOLVED: To provide a process for producing 1,5-dibromonaphthalene that can efficiently produce 1,5-dibromonaphthalene. SOLUTION: 1,5-dibromonaphthalene is produced by a process for producing 1,5-dibromonaphthalene having a bromination step of reacting at least one of naphthalene and 1-bromonaphthalene with bromine in the presence of a porous material. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0032-0049

(2018/03/23)

Composite taken as URAT 1 inhibitor
The invention provides a series of composite with a formula (I), wherein n is selected from 1, 2 or 3, X is selected from O or S, Q is selected from C or N, and R is selected from H, halogen or -C1-6.The composite can be used as the URAT 1 inhibitor and can be used for treating hyperuricemia and gout.
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Paragraph 0019

(2018/05/16)

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids
Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.
Quibell, Jacob M.,Perry, Gregory J. P.,Cannas, Diego M.,Larrosa, Igor
p. 3860 - 3865
(2018/04/26)

Fluorescence properties of 1-(silylethynyl)naphthalenes and 1,4-bis(silylethynyl)naphthalenes in solutions, thin films and solid states
1-(Silylethynyl)naphthalenes (1a-e) and 1,4-bis(silylethynyl)naphthalenes (2a-c) were prepared, and their fluorescence properties were evaluated in solutions, thin films and solid states. In dilute solutions, monomer emission is observed from substances in both groups and the relative fluorescence quantum yields of 1a-e increase as the steric bulk of the substituents on silicon increase. The observed concentration dependence of fluorescence intensities indicates that the self-quenching has a more pronounced effect on emission in shorter wavelength regions than that in longer wavelength regions. Analysis of Stern–Volmer type plots shows that formation of both an excimer and a termolecular excited complex is involved in fluorescence quenching of 1 in solution, whereas only an excimer is involved in quenching of 2. Fluorescence in thin films and solid states dispersion in KBr is dependent on number of silylethynyl groups present in the naphthalene derivatives. For example, excimer emission occurs from 1 while monomer emission occurs mainly from 2. X-ray crystallographic analysis of the crystal packing structure shows that 2b would have difficulty with forming an excimer because of steric hindrance, but that 2a can partially form an excimer owing to the slipped head-to-tail parallel orientation of naphthalene rings on neighboring molecules. The results of this effort demonstrate that the emission properties of 1- and 1,4-bis(silylethynyl)naphthalenes are influenced by the number of silylethynyl groups, the steric bulk of substituents on silicon atoms, and the compound's present state.
Maeda, Hajime,Fujii, Takayuki,Minamida, Keita,Mizuno, Kazuhiko
p. 153 - 160
(2017/04/21)

Polybrominated methoxy- and hydroxynaphthalenes
Regio- and stereoselective synthesis are described for convenient preparation of hydroxy- and methoxynaphthalenes starting from naphthalene (1). cis,cis,trans-2,3,5,8-Tetrabromo-4-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol (6), cis,cis,trans-2,3,5,8-tetrabromo-1,4-dimethoxy-1,2,3,4-tetrahydronaphthalene (7), and cis,cis,cis-2,3,5,8-tetrabromo-1,4-dimethoxy-1,2,3,4-tetrahydronaphthalene (8) were obtained with silver-induced substitution of trans,cis,trans-1,2,3,4, 5,8-hexabromo-1,2,3,4-tetrahydronaphthalene (3). Base-promoted aromatization of dimethoxides 7 and 8 afforded 3,5,8-tribromo-1-methoxynaphthalene (9) and 2,5,8-tribromo-1-methoxynaphthalene (10). The reaction of 6 with sodium methoxide formed compounds 10 and 3,5,8-tribromonaphthalen-1-ol (16). Bromination of 9 and 16 with Br2 in dichloromethane at room temperature produced 2,3,5,8-tetrabromo-1-methoxynaphthalene (14) and 2,3,4,5,8-pentabromonaphthalen-1-ol (18), respectively, while compound 10 did not react in the same conditions. Pyridine-induced elimination of hexabromide 3 afforded 1,4,6-tribromnaphthalene (21) in 99% yield and thermolysis of the hexabromide 3 gave mainly 1,4,6,7-tetrabromonaphthalene (22). Tetrabromide 22 was transformed to 1,4,6,7-tetramethoxynaphthalene (23) by copper-assisted nucleophilic substitution reaction.
Akar, Kiymet Berkil,?akmak, Osman,Tun?, Tuncay
p. 332 - 346
(2016/05/24)

WAVELENGTH CONVERSION MATERIAL FOR HIGHLY EFFICIENT DYE-SENSITIZED SOLAR CELL, AND PREPARATION METHOD THEREOF
Novel compounds represented by the present invention refers to formula 1 or formula 2, said novel compounds including wavelength change material, and including said wavelength change material relates to dye-sensitized solar cell.
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Paragraph 0232-0235

(2016/10/10)

PYRABACTIN ANALOGUES TO MODULATE PLANT DEVELOPMENT
The present invention relates to compounds which can be used to control plant development. Indeed, the present invention discloses a new class of pyrabactin analogues which have a physiological effect on -for example- seed germination, and/or stomatal closure, and/or have developmental effects on root and shoot development and organogenesis. Hence, the latter compounds can be used to control plant development such as -for example- increasing the tolerance of plants to drought stress or to control physiological phenomena such as pre-harvest sprouting, tolerance to pathogens etc.
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Page/Page column 10

(2015/09/23)

Phosphonamide pyrabactin analogues as abscisic acid agonists
A four step synthesis towards novel phosphonic pyrabactin analogues is presented. Via a stomatal closure and germination assay, the ability of the analogues to selectively induce the ABA-signaling pathway was demonstrated.
Van Overtveldt,Heugebaert,Verstraeten,Geelen,Stevens
supporting information
p. 5260 - 5264
(2015/05/13)

Direct arylation of oligonaphthalenes using PIFA/BF3· Et2O: From double arylation to larger oligoarene products
Direct dehydrogenative coupling between the linear ter- and quaternaphthalenes and substituted benzenes was achieved under the Kita conditions using the hypervalent PIFA/BF3 reagent. Products resulting from either the double arylation of the naphthalenic substrate or the formal dimerizative arylation have been prepared. For example, in the latter mode, ternaphthalene was converted into a series of linear octiarenes (counting the capping Ar). The process represents an alternative to the cross-coupling methodologies employed in related syntheses and proceeds via a selective functionalization of six relatively inert aromatic CH bonds.
Guo, Wusheng,Faggi, Enrico,Sebastian, Rosa M.,Vallribera, Adelina,Pleixats, Roser,Shafir, Alexandr
p. 8169 - 8175
(2013/09/12)

Synthesis of precursors for large-diameter hemispherical buckybowls and precursors for short carbon nanotubes
We report herein the synthesis of six precursor molecules for the rational synthesis of isomerically pure armchair, zigzag, or chiral single-walled carbon nanotubes (SWCNTs). The polycyclic aromatic hydrocarbons possess the required carbon connectivity for the generation of extended hemispherical buckybowls with predefined geometry through intramolecular cyclodehydrogenation. The precursors for the short carbon nanotubes and the large-diameter hemispherical buckybowls have potential for the rational initiation of single-chirality SWCNT growth on metal surfaces. The options for the construction of precursors for various SWCNT chiralities based on the suggested synthesis strategy are presented.
Mueller, Andreas,Amsharov, Konstantin Yu.
p. 6155 - 6164,10
(2020/09/16)

Functionalization of naphthalene: A novel synthetic route to brominated naphthoquinones
An efficient procedure is described for synthesis of 2,5,8- tribromonaphthoquinone (12) from naphthalene in four reaction steps. Silver-promoted solvolysis of hexabromide 3 produces the specific diastereostereoisomer 10. Dehydrobromination of 10 using sodium methoxide gives tribromodihydronaphthalene-1,4-diol 11 in high yield. PCC oxidation of either 10 or 11 results in the formation of 2,5,8-tribromonaphthalene-1,4-dione (12). ARKAT-USA, Inc.
Cakmak, Osman,Akar, Kiymet Berkil,Kaplan, Nuri
p. 274 - 281
(2013/01/16)

Wavelength conversion lanthanide(III)-cored complex for highly efficient dye-sensitized solar cells
Lanthanide(III)-cored complex as a wavelength conversion material has been successfully designed and synthesized for highly efficient dye-sensitized solar cells, for the first time, since light with a short wavelength has not been effectively used for generating electric power owing to the limited absorption of these DSSCs in the UV region. A black dye (BD) was chosen and used as a sensitizer, because BD has a relatively weak light absorption at shorter wavelengths. The overall conversion efficiency of the BD/WCM device was remarkably increased, even with the relatively small amount of WCM added to the device. The enhancement in Voc by WCM, like DCA, could be correlated with the suppression of electron recombination between the injected electrons and I3 - ions. Furthermore, the short-circuit current density was significantly increased by WCM with a strong UV light-harvesting effect. The energy transfer from the Eu(III)-cored complex to the TiO2 film occurred via the dye, so the number of electrons injected into the TiO2 surface increased, i.e., the short-circuit current density was increased. As a result, BD/WCM-sensitized solar cells exhibit superior device performance with the enhanced conversion efficiency by a factor of 1.22 under AM 1.5 sunlight: The photovoltaic performance of the BD/WCM-based DSSC exhibited remarkably high values, Jsc of 17.72 mA/cm2, Voc of 720 mV, and a conversion efficiency of 9.28% at 100 mW cm-2, compared to a standard DSSC with Jsc of 15.53 mA/cm2, Voc of 689 mV, and a conversion efficiency of 7.58% at 100 mW cm-2. Therefore, the Eu(III)-cored complex is a promising candidate as a new wavelength conversion coadsorbent for highly efficient dyesensitized solar cells to improve UV light harvesting through energy transfer processes. The abstract should be a single paragraph which summaries the content of the article.
Oh, Jung Hwan,Song, Hae Min,Eom, Yu Kyung,Ryu, Jung Ho,Ju, Myung Jong,Kim, Hwan Kyu
scheme or table
p. 2743 - 2750
(2012/02/01)

Palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides
The palladium-catalyzed conversion of aryl and vinyl triflates to aryl and vinyl halides (bromides and chlorides) has been developed using dialkylbiaryl phosphine ligands. A variety of aryl, heteroaryl, and vinyl halides can be prepared via this method in
Shen, Xiaoqiang,Hyde, Alan M.,Buchwald, Stephen L.
supporting information; experimental part
p. 14076 - 14078
(2011/01/10)

The role of neat substrates in phase-vanishing and tandem phase-vanishing reactions
Phase-vanishing reactions are triphasic reactions, which involve a reagent, a liquid perfluoroalkane as a phase screen and a substrate. Aromatization, isomerization and halogenation of neat substrates under phase-vanishing conditions gave the expected products in good to excellent yields. In tandem single-phase-phase-vanishing reaction, two reactants, placed in the top phase, afforded the intermediate, which in a subsequent phase-vanishing reaction reacted with the reagent from the bottom phase to give the final product. The reaction worked well under solvent-free conditions on liquid substrates and intermediates. With solids, results were better if an additional solvent was employed.
Windmon, Nicole,Dragojlovic, Veljko
scheme or table
p. 6543 - 6546
(2009/04/06)

3- (4-{ [4-(4-{ [3-(3, 3-DIMETHYL-1-PIPERIDINYL) PROPYL] 0XY} PHENYL) -1-PIPERIDINYL] CARBONYL }-1-NAPHTHALENYL) PROPANOIC OR PROPENOIC ACID AS H1 AND H3 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY AND/OR ALLERGIC DISORDERS
The present invention relates to a compound of formula (I), or a salt thereof wherein the naphthalene ring can be substituted in the 2, 3, 4, 5, 6, 7 or 8 position by R1, and R1 represents -CH2CH2COOH or -CH=C(CH3)COOH, and to processes for their preparation, to compositions containing them and to their use in the treatment of various diseases such as allergic rhinitis.
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Page/Page column 39

(2008/06/13)

Selective bromination of 1-bromonaphthalene: Efficient synthesis of bromonaphthalene derivatives
Selective and specific preparation methods are described for 1,4-dibromonaphthalene, 1,5-dibromonaphthalene and 1,3,5-tribromonaphthalene. The reaction of 1-bromonaphthalene and naphthalene with stoichometric quantities of bromine by using a minimum amount of solvent (methylene chloride) at -30 and -50°C smoothly affords 1,4-dibromonaphthalene in 90% yield. Photobromination of 1-bromonaphthalene in CCl4 at -30°C gives 1,2,3,4,5-pentabromo-1,2,3,4-tetrahydronaphthalenes, whereas 1,5-dibromonaphthalene is obtained at reflux (77°C) in 80% yield under the same conditions. Dehydrobromination of the pentabromide by t-BuOK affords 1,3,5-tribromonaphthalene as a sole product (91%). 1,5-Dibromo- and 1,3,5-tribromonaphthalenes were efficiently converted to the corresponding methoxy naphthalene derivatives.
Cakmak, Osman,Demirtas, Ibrahim,Balaydin, Halis T
p. 5603 - 5609
(2007/10/03)

Bromination of tetralin. Short and efficient synthesis of 1,4-dibromonaphthalene
High-temperature bromination of tetralin (1,2,3,4-tetrahydronaphthalene) with bromine resulted in benzylic biomination to give 1,4-dibromo-1,2,3,4-tetrahydronaphthalene (4) as a major product and several secondary products. Photolytic bromination of tetralin and subsequent double dehydrobromination of 1,1,4,4-tetrabromo-1,2,3,4-tetrahydronaphthalene (10) gave 1,4-dibromonaphthalene (11) as the sole product in a high yield. 1,4-Dibromonaphthalene is efficiently converted to the corresponding methoxy (12 and 13) and cyano (14 and 15) derivatives of naphthalene.
Cakmak, Osman,Kahveci, Ismail,Demirtas, Ibrahim,Hoekelek, Tuncer,Smith, Keith
p. 1791 - 1804
(2007/10/03)

Bromination of naphthalene and derivatives: High temperature bromination XI
Thermal and photobromination of naphthalene and derivatives have been studied. Several hexabromo- (12, 13, 16 and 17), and tetrabromotetralin derivatives (23, 24, and 25) have been obtained as the major products, besides bromonaphthalene derivatives. Base-promoted elimination reactions of 12, 13, 16 and 17 provided di- (8) tri- (10) and tetrabromo-naphthalenes (22). A convenient method was developed for the synthesis of 1,3- dibromonaphthalene (26) starting from (24). The structures of these products were determined by 1H-,13C- NMR data and X-ray structural analysis.
Dastan, Arif,Tahir, M. Nawaz,Uelkue, Dincer,Balci, Metin
p. 12853 - 12864
(2007/10/03)

Solid-state reaction of a lead tetraacetate - Metal halide system with naphthalene under mechanical activation
A mechanically activated solid-state reaction of halogenation of naphthalene with a Pb(OAc)4 - alkaline or alkaline-earth metal halide system was carried out to yield 1-halonaphthalene as the main reaction product and 1,4-dihalonaphthalene. The solid-state halogenation of naphthalene is more selective than a liquid-phase reaction.
Nikishin,Sokova,Makhaev,Petrova,Ignatenko,Kapustina
p. 1353 - 1355
(2007/10/03)

Bromination of Decalin and Its Derivatives. 9. High Temperature Bromination
Thermal and photobromination of decalin, 1, was studied, trans,cis,trans-2,5,7,9-tetrabromooctalin, 2, was obtained as the major product along with smaller amounts of bromonaphthalene derivatives. The structures of the products were determined by 1H- and 13C-NMR data and single X-ray structural analysis. Bromination of the two decalin derivatives 9 and 10 results in the formation of single isomers 11 and 12, respectively. The three tetrabromides 2, 11, and 12 were shown by molecular mechanics calculations to be the most stable stereoisomer in each case. The formation of these tetrabromides under thermodynamic control is postulated.
Dastan, Arif,Nawaz Tahir,Uelkue, Dincer,Shevlin, Philip B.,Balci, Metin
p. 4018 - 4022
(2007/10/03)

Selective Halogenation of Aromatic Hydrocarbons with Alumina-Supported Copper(II) Halides
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Kodomari, Mitsuo,Satoh, Hiroaki,Yoshitomi, Suehiko
p. 2093 - 2094
(2007/10/02)

New Dyes from Naphthostyril-5-carboxylic Acid: Synthesis of 6,12-Anthanthrenedione-3,4,9,10-tetracarboxylic Diimides, Naphthostyril-5,6-dicarboximides and 1-Amino-4-arylaminonaphthalene-5,8-dicarboxylic Bislactams
The novel vat dyes 6,12-anthanthrenedione-3,4,9,10-tetracarboxylic diimides (XIa-c) and the disperse dyes, naphthostyril-5,6-dicarboximides (XVIIIa-f) and bislactams (XIXa-d) have been synthesised from a common intermediate, naphthostyril-5-carboxylic acid (V).An improved method has also been developed for the synthesis of V.
Dalvi, S.S.,Seshadri, S.
p. 377 - 382
(2007/10/02)