13101-92-3

Usage

Uses

Used in Chemical Industry:
Naphthalene, 1-chloro-2-methoxyis used as a chemical intermediate for the synthesis of other compounds. Its unique structure and reactivity make it a valuable component in the production of various chemical products.
Safety Precautions:
It is advised to handle Naphthalene, 1-chloro-2-methoxywith caution as it can potentially cause skin, eye, and respiratory irritation. Proper safety measures, such as wearing protective gear and working in a well-ventilated area, should be taken to minimize the risk of exposure.

Upstream product

• 128-09-6 N-chloro-succinimide 
• 93-04-9 2-Methoxynaphthalene 
• 6921-17-1 1-chloro-5,5-dimethylhydantoin 
• 118-52-5 1,3-dichloro-5,5-dimethylhydantoin 
• 74-87-3 methylene chloride 
• 633-99-8 1-chloro-2-naphthol 
• 77-78-1 dimethyl sulfate 
• 79-24-3 Nitroethane 
• 628-13-7 pyridine hydrochloride 
• 79-46-9 2-nitropropane 
• 135-19-3 β-naphthol 
• 10026-13-8 phosphorus pentachloride 
• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 5392-12-1 2-methoxy-1-naphthaldehyde 

Downstream Products

• 633-99-8 1-chloro-2-naphthol 
• 2246-42-6 2-methoxynaphthylamine 
• 13101-93-4 1-(5-chloro-6-methoxynaphthalen-2-yl)ethan-1-one 
• 75907-52-7 2-methoxy-1-phenylnaphthalene 
• 17580-30-2 1-Chlor-2-methoxy-6-chlormethyl-naphthalin 
• 22204-53-1 (2S)-2-(6-methoxy(2-naphthyl))propanoic acid 
• 89617-86-7 (S)-2-(1-chloro-2-methoxynaphthalen-6-yl)propanoic acid 
• 128064-68-6 ethyl (6-methoxy-2-naphthyl)(2,6-xylylhydrazono)acetate 
• 128064-69-7 ethyl (5-chloro-6-methoxy-2-naphthyl)(2,6-xylylhydrazono)acetate 
• 17579-79-2 2-methyl-6-hydroxynaphthalene 
• 1021176-79-3 1-mesityl-2'-methoxynaphthalene 
• 1200804-92-7 3-(4-benzyl-5,6-dihydropyridin-1(2H)-yl)-1-(5-chloro-6-methoxynaphthalen-2-yl)propan-1-ol 
• 1200804-66-5 4-benzyl-1-(3-(5-chloro-6-methoxynaphthalen-2-yl)-3-hydroxypropyl)piperidin-4-ol 
• 1394148-08-3 3-(4-benzyl-5,6-dihydropyridin-1(2H)-yl)-1-(5-chloro-6-methoxynaphthalen-2-yl)propan-1-one hydrochloride 

Relevant academic research and scientific papers

Decarbonylative halogenation by a vanadium complex

Metal-catalyzed halogenation of the C-H bond and decarbonylation of aldehyde are conventionally done in nature. However, metal-mediated decarbonylative halogenation is unknown. We have developed the first metal-mediated decarbonylative halogenation reaction starting from the divanadium oxoperoxo complex K3V5+2(O 22-)4(O2-)2(μ-OH) (1). A concerted decarbonylative halogenation reaction was proposed based on experimental observations.

Cobalt-Catalyzed Enantioselective C–H Arylation of Indoles

Atropoisomeric (hetero)biaryls are scaffolds with increasing importance in the pharmaceutical and agrochemical industries. Although it is the most obvious disconnection to construct such compounds, the direct enantioselective C–H arylation through the concomitant induction of the chiral information remains extremely challenging and uncommon. Herein, the unprecedented earth-abundant 3d-metal-catalyzed atroposelective direct arylation is reported, furnishing rare atropoisomeric C2-arylated indoles. Kinetic studies and DFT computation revealed an uncommon mechanism for this asymmetric transformation, with the oxidative addition being the rate- and enantio-determining step. Excellent stereoselectivities were reached (up to 96% ee), while using an unusual N-heterocyclic carbene ligand bearing an essential remote substituent. Attractive dispersion interactions along with positive C–H-π interactions exerted by the ligand were identified as key factors to guarantee the excellent enantioselection.

Efficient halogenation synthesis method of aryl halide

The invention discloses an efficient halogenation synthesis method of aryl halide. The method comprises the following step: in the presence of a catalyst (sulfoxide or oxynitride), a halogenation reagent and a solvent, carrying out a halogenation reaction on an aromatic ring compound to obtain the aryl halide. According to the present invention, in the presence of a catalyst (sulfoxide or nitrogenoxide), a halogenation reagent and a solvent, the aromatic ring is subjected to an efficient halogenation reaction, such that the very useful aryl halide can be obtained with high activity and high selectivity; and by adopting the method disclosed by the invention, aryl halides can be efficiently synthesized, and the method has a wide application prospect in actual production.

Sulfoxide-Promoted Chlorination of Indoles and Electron-Rich Arenes with Chlorine as Nucleophile

An efficient chlorination of indoles and electron-rich arenes with chlorine anion as nucleophile is described. With the use of ethyl phenyl sulfoxide as the promoter, the reaction went smoothly under metal-free and mild conditions. Various indoles and electron-rich arenes are converted into the corresponding chlorinated compounds in moderate to excellent yields. A plausible interrupted Pummerer reaction mechanism was proposed without the oxidation of chloride anion. In addition, the byproduct thioether could be easily converted to the starting material sulfoxide just by a simple oxidation reaction. (Figure presented.).

Oxidative Photochlorination of Electron-Rich Arenes via in situ Bromination

Electron-rich arenes are oxidatively photochlorinated in the presence of catalytic amounts of bromide ions, visible light, and 4CzIPN as organic photoredox catalyst. The substrates are brominated in situ in a first photoredox-catalyzed oxidation step, followed by a photocatalyzed ipso-chlorination, yielding the target compounds in high ortho/para regioselectivity. Dioxygen serves as a green and convenient terminal oxidant. The use of aqueous hydrochloric acid as the chloride source reduces the amount of saline by-products.

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol

Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.

In Situ Formed IIII-Based Reagent for the Electrophilic ortho-Chlorination of Phenols and Phenol Ethers: The Use of PIFA-AlCl3 System

A new and in situ formed reagent generated by mixing PIFA {bis[(trifluoroacetoxy)iodobenzene]} and AlCl3 was introduced in the organic synthesis for the direct and highly regioselective ortho-chlorination of phenols and phenol ethers. An efficient electrophilic chlorination for these electron-rich arenes as well as the scope of the reaction are described herein. An easy, practical, and open-flask reaction allowed us to introduce a chlorine atom, which is a highly important functional group in organic synthesis. The reproducibility of our method has been demonstrated on gram-scale by carrying out the reaction in 6-bromo-2-naphthol. This halogenation reaction also proceeds in excellent conditions by first preparing the iodine(III)-based chlorinating reagent. Our new chlorinating reagent can be stored at least for two weeks at 4 °C without losing its reactivity.

Iron(III)-Catalyzed Chlorination of Activated Arenes

A general and regioselective method for the chlorination of activated arenes has been developed. The transformation uses iron(III) triflimide as a powerful Lewis acid for the activation of N-chlorosuccinimide and the subsequent chlorination of a wide range of anisole, aniline, acetanilide, and phenol derivatives. The reaction was utilized for the late-stage mono- and dichlorination of a range of target compounds such as the natural product nitrofungin, the antibacterial agent chloroxylenol, and the herbicide chloroxynil. The facile nature of this transformation was demonstrated with the development of one-pot, tandem, iron-catalyzed dihalogenation processes allowing highly regioselective formation of different carbon-halogen bonds. The synthetic utility of the resulting dihalogenated aryl compounds as building blocks was established with the synthesis of natural products and pharmaceutically relevant targets.

A Doubly Biomimetic Synthetic Transformation: Catalytic Decarbonylation and Halogenation at Room Temperature by Vanadium Pentoxide

The halogenation of the C?H bond by metal-oxo-peroxo species and the decarbonylation of aldehydes by metal-peroxo species are performed routinely in biological systems. However, metal-mediated decarbonylative halogenation is unknown in nature. In this work, we have shown that widely available V2O5 and VO(acac)2 (acac=acetylacetonate) can catalyze decarbonylative halogenation through the generation of an intermediate vanadium-oxo-peroxo species, which was characterized by using 51 V NMR, UV/Vis, and resonance Raman spectroscopy. Further detection of formic acid from the reaction mixture confirmed the biomimetic aspects of decarbonylative halogenation. A detailed experimental and DFT study indicated a concerted mechanism for this decarbonylative halogenation performed under simple and mild reaction conditions.

Aromatic Monochlorination Photosensitized by DDQ with Hydrogen Chloride under Visible-Light Irradiation

Photochlorination of aromatic substrates by hydrogen chloride with 2,3-dichloro-5,6-cyano-p-benzoquinone (DDQ) occurs efficiently to produce the corresponding monochlorinated products selectively under visible-light irradiation. The yields for the chlorination of phenol were 70 % and 18 % for p- and o-chlorophenol, respectively, without formation of further chlorinated products. The photoinduced chlorination is initiated by electron transfer from Cl- to the triplet excited state of DDQ. The radical intermediates involved in the photochemical reaction have been detected by time-resolved transient absorption measurements.