18539-44-1

Basic information

• Product Name: (±)-2-[(4-fluorobenzyl)oxy]tetrahydropyran
• Synonyms: (±)-2-[(4-fluorobenzyl)oxy]tetrahydropyran
• CAS NO: 18539-44-1
• Molecular Weight: 210.248
• Mol File: 18539-44-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (±)-2-[(4-fluorobenzyl)oxy]tetrahydropyran(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-2-[(4-fluorobenzyl)oxy]tetrahydropyran(18539-44-1)
• EPA Substance Registry System: (±)-2-[(4-fluorobenzyl)oxy]tetrahydropyran(18539-44-1)

Safety Data

• Hazardous Substances Data: 18539-44-1(Hazardous Substances Data)

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 459-56-3 4-fluorobenzylic alcohol 
• 14629-55-1 (4-fluorobenzyloxy)trimethylsilane 
• 142-68-7 TETRAHYDROPYRANE 

Downstream Products

• 456-19-9 4-fluorobenzal chloride 
• 459-56-3 4-fluorobenzylic alcohol 
• 459-23-4 4-fluorobenzaldoxime 
• 459-57-4 4-fluorobenzaldehyde 

Relevant articles and documents

Unexpected Mild Protection of Alcohols as 2-O-THF and 2-O-THP Ethers Catalysed by Cp2TiCl Reveal an Intriguing Role of the Solvent in the Single-Electron Transfer Reaction

A method for the conversion of primary, secondary and tertiary alcohols into the corresponding THF ethers at room temperature and primary and secondary alcohols into the corresponding THP ethers, has been developed using titanium(III) species generated from a catalytic amount of titanocene dichloride or (4R,5R)-(-)-2,2-dimethyl-α,α,α′,α′-tetra(1-naphthyl)-1,3-dioxolane-4,5-dimethanolatotitanium(IV) dichloride:acetonitrile adduct together with manganese(0) as a reductant and bromoform in THF or THP as the solvent. A radical mechanism is proposed for this transformation revealing an intriguing role of the solvent in the single-electron transfer reactions catalysed by the low valent TiIII system. A set of primary, secondary and benzylic alcohols have been converted into the corresponding THF and THP ethers and tertiary alcohols into the corresponding THF ethers using a catalytic amount of titanium dichloride in good yields and mild reaction conditions.

Direct Conversion of TMS-ethers to THP-ethers Catalyzed by {[K.18-Crown-6]Br3}n

-

Selective tetrahydropyranylation of alcohols and phenols using titanium(IV) salophen trifluoromethanesulfonate as an efficient catalyst

Titanium(IV) salophen trifluoromethanesulfonate, [TiIV(salophen)(OSO2CF3)2], as a catalyst enables selective tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran. Using this catalytic system, primary, secondary and tertiary alcohols, as well as phenols, were converted to their corresponding tetrahydropyranyl ethers in high yields and short reaction times at room temperature. Investigation of the chemoselectivity of this method showed discrimination between the activity of primary alcohols in the presence of secondary and tertiary alcohols and phenols. This heterogenized catalyst could be reused several times without loss of its catalytic activity. Copyright