183200-85-3

Basic information

• Product Name: 6-(4-methoxyphenyl)naphthalen-2-ol
• Synonyms: 6-(4-methoxyphenyl)naphthalen-2-ol
• CAS NO: 183200-85-3
• Molecular Weight: 250.297
• Mol File: 183200-85-3.mol

Chemical Properties

• CAS DataBase Reference: 6-(4-methoxyphenyl)naphthalen-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(4-methoxyphenyl)naphthalen-2-ol(183200-85-3)
• EPA Substance Registry System: 6-(4-methoxyphenyl)naphthalen-2-ol(183200-85-3)

Safety Data

• Hazardous Substances Data: 183200-85-3(Hazardous Substances Data)

Upstream product

• 15231-91-1 6-bromo-naphthalen-2-ol 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 380861-01-8 6-hydroxy-2-(4′-hydroxyphenyl)naphthalene 
• 1122065-36-4 6-(4-methoxyphenyl)naphthalen-2-yl pivalate 
• 1334136-79-6 C₂₁H₂₁BrO₂ 
• 602-09-5 1,1'-bi-2-naphthol 

Relevant articles and documents

Iron-Catalyzed Room Temperature Cross-Couplings of Bromophenols with Aryl Grignard Reagents

Herein we report a room temperature Fe-catalyzed coupling reaction of various bromophenols with aryl Grignard reagents, which exhibits a wide substrate scope and high functional group tolerance. For the first time, the combination of simple Fe(acac)3/PBu3/Ti(OEt)4 has been used as an effective catalyst for the biaryl couplings of bromophenols or their Na or K salts with debromination and etherification side reactions being well suppressed. Various biphenols including natural product garcibiphenyl C as well as pharmaceutical diflunisal and its ethyl ester were facilely synthesized using the present protocol. (Figure presented.).

The Interrupted Pummerer Reaction in a Sulfoxide-Catalyzed Oxidative Coupling of 2-Naphthols

A benzothiophene S-oxide catalyst, generated in situ by sulfur oxidation with H2O2, mediates the oxidative coupling of 2-naphthols. Key to the catalytic process is the capture and inversion of reactivity of a 2-naphthol partner, using an interrupted Pummerer reaction of an unusual benzothiophene S-oxide, followed by subsequent coupling with a second partner. The new catalytic manifold has been showcased in the synthesis of the bioactive natural products, (±)-nigerone and (±)-isonigerone. Although Pummerer reactions are used widely, their application in catalysis is rare, and our approach represents a new catalytic manifold for metal-free C?C bond formation.

Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols

An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high yields. Gram-scale reactions, as well as the scope of this protocol, were explored with electron-rich and electron-poor phenols as well as heterocycles. Quantum chemistry calculations revealed PhII(OH)·NH3 to be the most plausible iodinating active species as a reactive "I+" synthon. In light of the relevance of the iodoarene moiety, we present herein a practical, efficient, and simple procedure with a broad functional group scope that allows access to the iodoarene core unit.

α-Nitro-α,β-Unsaturated Ketones: An Electrophilic Acyl Transfer Reagent in Catalytic Asymmetric Friedel-Crafts and Michael Reactions

Herein, we introduce α-nitro-α,β-unsaturated ketones as efficient electrophilic acyl transfer reagents, and they were employed in Friedel-Crafts as well as in Michael reactions. The desired acyl transfer products of these reactions were obtained in high yields with high to excellent enantioselectivities with t-leucine-derived squaramide catalyst under mild reaction conditions. Few applications including a synthesis of the isoxazoline motif have been demonstrated.

Enantioselective Oxidative Homocoupling and Cross-Coupling of 2-Naphthols Catalyzed by Chiral Iron Phosphate Complexes

Novel chiral iron phosphate complexes were prepared as catalysts for asymmetric oxidative coupling reactions. These catalysts were applied for the synthesis of enantio-enriched C1- and C2-symmetric BINOLs, in which the 3 and 3′ positions are available for chemical modifications. It was proposed that the reaction takes place via an oxidative radical-anion coupling mechanism. A destructive BINOL racemization that competes with the enantioselective oxidative coupling of 2-naphthols was revealed, thereby offering new insights into this highly important reaction.

Dibenzosiloles and 12H-indololo[3,2-d] naphtho[1,2-b][1]siloles: Exploration of organic chromophores exhibiting efficient solid-state fluorescence

The construction of a diorganosilylene bridge over a biaryl moiety at the 2,2?- positions is a versatile strategy for fine-tuning its HOMO-LUMO energy gap, which is closely linked to the electronic and optical properties of the compounds. Therefore, there

The polymerizable compound (by machine translation)

PROBLEM TO BE SOLVED: To provide a liquid crystal display element that has enhanced productivity and reliability by improvement of curability of a polymerizable liquid crystal composition, improved display characteristics such as stability enhancement

Synthesis of aryl-substituted naphthalene-linked pyrrolobenzodiazepine conjugates as potential anticancer agents with apoptosis-inducing ability

A library of new aryl-substituted naphthalene C8-linked pyrrolo[2,1-c][1,4]benzodiazepine (PBD) conjugates with various linker architectures were designed, synthesized, and evaluated for their anticancer activity against a panel of 11 human cancer cell lines. All 32 conjugates show anticancer potential, with some of them exhibiting particularly high activity (0.01-0.19μM). Thermal denaturation studies showed effective DNA binding capacity relative to DC-81. In assays for biological activity relating to cell-cycle distribution, these PBD conjugates induce G0/G1-phase arrest and also cause an increase in the levels of p53 and caspase-9 proteins, followed by apoptotic cell death. One conjugate in particular is the most promising candidate of the series, with the potential to be selected for further studies, either alone or in combination with existing anticancer therapies. Getting into the groove: Pyrrolobenzodiazepine (PBD) conjugates showed an effective ability to bind DNA. They induce G0/G1-phase arrest, enhance the expression levels of p53 and caspase-9, and induce apoptosis. One conjugate stands out as particularly promising; it is a suitable candidate for further study, either alone or in combination with current anticancer therapies.

PHEN-NAPHTHALENE AND PHEN-QUINOLINE DERIVATIVES AND THEIR USE FOR BINDING AND IMAGING AMYLOID PLAQUES

This invention relates to methods of imaging amyloid deposits, radiolabeled compounds, and methods of making radiolabeled compounds useful in imaging amyloid deposits. This invention also relates to compounds and methods of making compounds for inhibiting the aggregation of amyloid proteins to form amyloid deposits and methods of delivering therapeutic agents to amyloid deposits.