19817-09-5

Basic information

• Product Name: 1,1'-Binaphthalene, 4,4'-dimethoxy-
• Synonyms: 4,4'-dimethoxy-1,1'-binaphthyl;4,4-dimethoxy-1,1'-binaphthalene;1,1'-Binaphthalene,4,4'-dimethoxy
• CAS NO: 19817-09-5
• Molecular Formula: C22H18O2
• Molecular Weight: 314.384
• Mol File: 19817-09-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1,1'-Binaphthalene, 4,4'-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-Binaphthalene, 4,4'-dimethoxy-(19817-09-5)
• EPA Substance Registry System: 1,1'-Binaphthalene, 4,4'-dimethoxy-(19817-09-5)

Safety Data

• Hazardous Substances Data: 19817-09-5(Hazardous Substances Data)

Upstream product

• 173313-25-2 di-(4-methoxy-1-naphthyl) methylphosphate 
• 2216-69-5 1-Methoxynaphthalene 
• 509-14-8 tetranitromethane 

Relevant articles and documents

Selective synthesis of 1,1'-binaphthalene derivatives by oxidative coupling with TiCl4

Oxidative coupling of naphthalene compounds with TiCl4 in nitromethane under mild conditions gives symmetrical 1,1'-binaphthyls in good yields. The method is particularly useful when applied to substrates with electron donating groups. (C) 2000 Elsevier Science Ltd.

Intramolecular Binaphthyl Formation from Radical Cations of Tri-1-naphthyl Phosphate and Related Compounds in Photoinduced Electron-Transfer Reactions Sensitized by 9,10-Dicyanoanthracene

The photoinduced electron transfer of tri-1-naphthyl phosphate and related compounds sensitized by 9,10-dicyanoanthracene (DCA) in acetonitrile produces 1,1′-binaphthyl and the corresponding biaryl. The quenching rate constant of the DCA fluorescence is calculated to be equal to the diffusion-controlled rate constant from the Stern-Volmer analysis and the fluorescence lifetime measurement. The free energy change calculated from the redox potentials and excitation energy of the singlet excited DCA indicates that the quenching process occurs exergonically to give the tri-1-naphthyl phosphate radical cation and DCA radical anion through electron transfer from tri1-naphthyl phosphate to the singlet excited DCA at the diffusion-controlled rate. On the basis of spectroscopic and kinetic studies with laser flash photolysis, pulse radiolysis, and γ-radiolysis, the radical cation of tri-1-naphthyl phosphate forms an intramolecular π-dimer radical cation with face-to-face interaction between the two naphthyl groups within 8 ns of the electron pulse. The 1,1′-binaphthyl radical cation is eliminated at the rate constant of kr = 5.3 × 105 s~: from the intramolecular π-dimer radical cation. Branching ratios of the reaction pathways are estimated for the reactive intermediates such as the tri-1-naphthyl phosphate radical cation and its intramolecular π-dimer radical cation from the rate constants and quantum yields. The electron-withdrawing character of the P(O) group in the O-P(O)-O spacer is responsible for the elimination of the binaphthyl radical cation. The DCA-sensitized photoinduced electron-transfer reaction of the tri-1-naphthyl phosphate is compared with the direct photoreaction.

Regioselective Halogenation and Dimerization of Alkoxynaphathalenes with Alumina- or Kieselguhr-supported Copper(II) Halides

The reaction of 1-alkoxynaphathalenes 1 with alumina-supported copper(II) bromide or copper(II) chloride gave dimers, 4,4'-dialkoxy-1,1'-binaphthyls 3, as major products, and with Kieselguhr-supported copper(II) bromide afforded 1-bromo-4-alkoxynaphthalenes 2, while the reaction of 2-alkoxynaphathalenes 4 with alumina- or Kieselguhr-supported copper(II) bromide gave preferentially 1-bromo-2-alkoxynaphthalenes 5.