93952-05-7

Basic information

• Product Name: DIPHENYL-D10 ETHER
• Synonyms: DIPHENYL-D10 ETHER;DIPHENYL ETHER (D10);PHENYL ETHER (D10);6,6'-Oxybisbenzene-d5
• CAS NO: 93952-05-7
• Molecular Formula: C₁₂H₁₀O
• Molecular Weight: 180.27
• Mol File: 93952-05-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: DIPHENYL-D10 ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: DIPHENYL-D10 ETHER(93952-05-7)
• EPA Substance Registry System: DIPHENYL-D10 ETHER(93952-05-7)

Safety Data

• Hazardous Substances Data: 93952-05-7(Hazardous Substances Data)

Upstream product

• 4165-57-5 bromobenzene-d5 
• 13127-88-3 phenol-d6 
• 101-84-8 diphenylether 

Relevant articles and documents

Efficient continuous-flow HD exchange reaction of aromatic nuclei in D2O/2-PrOH mixed solvent in a catalyst cartridge packed with platinum on carbon beads

Herein, a continuous-flow deuteration methodology for various aromatic compounds is developed based on heterogeneous platinum-catalyzed hydrogen-deuterium exchange. The reaction entails the transfer of a substrate dissolved in a mixed solvent of 2-propanol and deuterium oxide into a catalyst cartridge packed with platinum on carbon beads (Pt/CB). Pt/ CB could be continuously used without significant deterioration of catalyst activity for at least 24 h. Deuteration proceeded within 60 s of the substrate solutions being passed through the Pt/CB layer in the Pt/CB-packed cartridge.

Mechanisms of the photochemical rearrangement of diphenyl ethers

The mechanism of the photochemical rearrangement of diphenyl ether (1a) was studied. Irradiation of 1a in ethanol gave 2-phenylphenol (2, 42%) and 4-phenylphenol (3, 11%) as rearrangement products, in addition to phenol (4, 30%) and benzene (5, 25%) as diffusion products. Cross-coupling experiments employing [2H10]1a demonstrated that the formation of 2- and 4-phenylphenol was an intramolecular process. Irradiation of 1a in benzene or in toluene gave biphenyls in good yields. The combined yields of rearrangement products (2 and 3) increased with increase of solvent viscosity, with a concomitant decrease in the formation of 4. All the results can be rationalized in terms of excitation of 1a to the singlet state and dissociation to a radical pair intermediate involving phenoxy and phenyl radicals. Intramolecular recombination of these radicals gives rearrangement products, and escape followed by hydrogen abstraction from the solvent gives diffusion products. When position 4 of 1a was occupied by an electron-donating substituent (1b-e), aryloxy-phenyl bond cleavage to give the corresponding rearrangement products prevailed over phenoxy-aryl bond cleavage. The opposite was the case for substrates with an electron-withdrawing substituent at position 4 (1h,i).