85477-63-0

Usage

Type of compound

Brominated derivative of naphthalene

Uses

Pesticide and insecticide

Toxicity

Highly toxic

Health hazards

Causes skin and eye irritation, respiratory problems if inhaled

Environmental impact

Highly harmful to aquatic organisms

Physical state

White crystalline solid

Solubility

Insoluble in water, soluble in organic solvents

Agricultural applications

Control of pests and insects

Safety precautions

Handle with care, follow proper safety protocols

Upstream product

• 20027-95-6 1,5-Dibromo-2,6-dimethylnaphthalene 
• 581-42-0 2.6-dimethylnaphthalene 
• 128-08-5 N-Bromosuccinimide 

Downstream Products

• 29041-32-5 <2.2> (2,6)naphthalenophane (achiral) 

Relevant academic research and scientific papers

Naphtho[1,2-c:5,6-c]difuran: A Reactive Linker and Cyclophane Precursor

Naphtho[1,2-c:5,6-c]difuran has been isolated in a 9-step synthesis from 2,6-dimethylnaphthalene. It is a highly reactive diene similar in nature to the related isobenzofuran. In Diels-Alder reactions, its intermediate monoadducts are actually less reactive that the parent difuran making possible sequential Diels-Alder reactions with different dienophiles. Reaction with a tethered bis(dienophile) leads to the production of a naphthalenic cyclophane.

Coupling N-H Deprotonation, C-H Activation, and Oxidation: Metal-Free C(sp3)-H Aminations with Unprotected Anilines

An intramolecular oxidative C(sp3)-H amination from unprotected anilines and C(sp3)-H bonds readily occurs under mild conditions using t-BuOK, molecular oxygen and N,N-dimethylformamide (DMF). Success of this process, which requires mildly acidic N-H bonds and an activated C(sp3)-H bond (BDE 85 kcal/mol), stems from synergy between basic, radical, and oxidizing species working together to promote a coordinated sequence of deprotonation: H atom transfer and oxidation that forges a new C-N bond. This process is applicable for the synthesis of a wide variety of N-heterocycles, ranging from small molecules to extended aromatics without the need for transition metals or strong oxidants. Computational results reveal the mechanistic details and energy landscape for the sequence of individual steps that comprise this reaction cascade. The importance of base in this process stems from the much greater acidity of transition state and product for the 2c,3e C-N bond formation relative to the reactant. In this scenario, selective deprotonation provides the driving force for the process.

Nonplanar Ladder-Type Polycyclic Conjugated Molecules: Structures and Solid-State Properties

Using an efficient intramolecular carbon-carbon cross-coupling reaction, a series of new ladder-type conjugated molecules have been prepared successfully in high yields. Such a pyran-fused polycylic structure possesses an extended π-conjugated backbone with flexible conformation, which gives these molecules interesting properties, including high solubility in common organic solvents, excellent thin film-forming abilities, blue fluorescent emission with good quantum yields, and aggregate formation in a binary solvent. The self-assembly behaviors of these molecules as well as various nanostructures can be finely tailored by varying the substituted group on the molecular periphery. The powder and single-crystal X-ray diffraction analyses revealed that the synergetic effect of π-π stacking and van der Waals interactions play a key role in controlling the morphologies of these aggregates. More importantly, self-assembled molecules exhibit good fluorescent performance, due to their twist backbone conformation. (Figure Presented).

Gold(I) styrylbenzene, distyrylbenzene, and distyrylnaphthalene complexes: High emission quantum yields at room temperature

One gold(I)-substituted styrylbenzene, six digold(I) distyrylbenzenes, one tetragold distyrylbenzene, and four digold distyrylnaphthalene complexes were synthesized using base-promoted auration, alkynylation, triazolate formation, and Horner-Wadsworth-Emmons reactions. The gold(I) fragments are either σ-bonded to the aromatic system, or they are attached through an alkynyl or triazolate spacer. Product formation was monitored using 31P{ 1H} NMR spectroscopy. Systems in which gold(I) binds to the central benzene ring or the terminal phenyl rings were designed. All of these complexes have strong ultraviolet absorptions and emit blue light. The position of the gold(I) attachment influences the luminescence efficiency. Complexes with two gold(I) fragments attached to the ends of the conjugated system have fluorescence quantum yields up to 0.94, when using 7-diethylamino-4- methylcoumarin as the emission standard. Density-functional theory calculations on three high-yielding emitters suggest that luminescence originates from the distyrylbenzene or -naphthalene bridge. Copyright

Molecular tuning of phenylene-vinylene derivatives for two-photon photosensitized singlet oxygen production

(Chemical Equation Presented) Substituent-dependent features and properties of the sensitizer play an important role in the photosensitized production of singlet oxygen, O2(a1Δg). In this work, we systematically examine the effect of molecular changes in the sensitizer on the efficiency of singlet oxygen production using, as the sensitizer, oligophenylene-vinylene derivatives designed to optimally absorb light in a nonlinear two-photon process. We demonstrate that one cannot always rely on rule-of-thumb guidelines when attempting to construct efficient two-photon singlet oxygen sensitizers. Rather, as a consequence of behavior that can deviate from the norm, a full investigation of the photophysical properties of the system is generally required. For example, it is acknowledged that the introduction of a ketone moiety to the sensitizer chromophore often results in more efficient production of singlet oxygen. However, we show here that the introduction of a carbonyl into a given phenylene-vinylene can, rather, have adverse effects on the yield of singlet oxygen produced. Using these molecules, we show that care must also be exercised when using qualitative symmetry-derived arguments to predict the relationship between one-and two-photon absorption spectra.

Naphtho[1,2-c;5,6-c]difuran, a stable isobenzofuran derivative

The title compound, an interesting analog of isobenzofuran, was prepared in nine steps from 2,6-dimethylnaphthalene in an overall yield of 12%. Copyright (C) 1996 Elsevier Sciences Ltd.

Transanular Interactions in Phanes, 26. Models for Excimers: Achiral and Chiral(2,6)Naphthalinophane

The achiral(2,6)naphthalenophane diastereomer 1 which was not obtained previously, was synthesized by using dibromo-substitution to force the formation of 3 besides 4 in the vacuum pyrolysis of the disulfone 12.Debromination of 3/4 via halogen-metal-exchange followed by hydrolysis gave a mixture of 1/2 from which 1 could be isolated and characterized.