82994-19-2

Basic information

• Product Name: 3,5-dimethoxyphenyl phenyl ether
• Synonyms: 3,5-dimethoxyphenyl phenyl ether
• CAS NO: 82994-19-2
• Molecular Weight: 230.263
• Mol File: 82994-19-2.mol

Chemical Properties

• CAS DataBase Reference: 3,5-dimethoxyphenyl phenyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-dimethoxyphenyl phenyl ether(82994-19-2)
• EPA Substance Registry System: 3,5-dimethoxyphenyl phenyl ether(82994-19-2)

Safety Data

• Hazardous Substances Data: 82994-19-2(Hazardous Substances Data)

Upstream product

• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 100-67-4 potassium phenolate 
• 500-99-2 3,5-dimethoxyphenol 
• 507233-69-4 triphenyl bismuth ⁽²⁺⁾; dichloride 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 7051-16-3 1-chloro-3,5-dimethoxybenzene 
• 108-95-2 phenol 
• 108-86-1 bromobenzene 

Downstream Products

• 666180-48-9 5-phenoxy-resorcinol 

Relevant articles and documents

Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides

The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.

Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings

Diaryl formation is achieved by coupling phenols and (hetero)aryl halides under the catalysis of CuI/N,N′-bis(2-phenylphenyl) oxalamide (BPPO) or CuI/N-(2-phenylphenyl)-N′-benzyl oxalamide (PPBO) at 90 °C using DMF or MeCN as the solvent. Only 0.2-2 mol % CuI and ligand are required for complete conversion, which represents the lowest catalytic loadings for a general Cu/ligand-catalyzed diaryl ether formation.

CuI/oxalamide catalyzed couplings of (hetero)aryl chlorides and phenols for diaryl ether formation

Couplings between (hetero)aryl chlorides and phenols can be effectively promoted by CuI in combination with an N-aryl-N′-alkyl-substituted oxalamide ligand to proceed smoothly at 120 °C. For this process, N-aryl-N′-alkyl-substituted oxalamides are more effective ligands than bis(N-aryl)-substituted oxalamides. A wide range of electron-rich and electron-poor aryl and heteroaryl chlorides gave the corresponding coupling products in good yields. Satisfactory conversions were achieved with electron-rich phenols as well as a limited range of electron-poor phenols. Catalyst and ligand loadings as low as 1.5 mol % are sufficient for the scaled-up variants of some of these reactions. Aryl and alkyl: N-Aryl-N′-alkyl-substituted oxalamide ligands promote the CuI catalyzed coupling of (hetero)aryl chlorides and phenols at 120 °C more effectively than bis(N-aryl)-substituted oxalamides. A wide range of electron-rich and electron-poor aryl and heteroaryl chlorides were converted into the corresponding coupling products in good yields.

THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS. PART X. STUDIES ON THE PHENYLATION AND OXIDATION OF PHENOLS

The influence of the substituents on the phenol on the regiochemistry of the arylation reactions with Ph3BiCl2 and other bismuth reagents has been studied.O-Phenylation occurs with phenols substituted with electron-withdrawing groups.Electron-donating substituted phenols undergo ortho C-phenylation.Oxidative dimerisation has been observed with 2,6-dialkyl phenols.

COPPER CATALYSED O-PHENYLATION OF PHENOLS AND ENOLS BY PENTAVALENT ORGANOBISMUTH COMPOUNDS

The O-phenylation of phenols under neutral conditions by Bi(V) reagents is strongly catalysed by copper salts and by copper powder, even at room temperature.Enolic systems are also subject to copper powder catalysis and give exclusively O-phenylation.