141765-56-2

Usage

Physical state

Colorless, odorless liquid

Industrial applications

Solvent in adhesives, coatings, and resins
Precursor in the synthesis of other organic compounds

Uses in personal care and pharmaceuticals

Stabilizer in formulation

Antimicrobial properties

Effective antimicrobial agent

Applications in cosmetics and skincare

Ingredient in certain cosmetic and skincare products

Research and industry interest

Significant interest to researchers and industry professionals

Upstream product

• 109-99-9 tetrahydrofuran 
• 98-86-2 acetophenone 
• 230285-22-0 1-(acetoxy)-1-methyl-1-phenyl-5-(N-phthalimidoxy)pentane 
• 230285-20-8 5-(tert-butyldiphenylsiloxy)-1-methyl-1-phenyl-1-pentanol 
• 230285-21-9 1-acetoxy-5-(tert-butyldiphenylsiloxy)-1-methyl-1-phenylpentane 
• 1011-62-7 5-hydroxy-1-phenylpentan-1-one 
• 141883-58-1 1-acetoxy-1-methyl-1-phenyl-5-pentanol 
• 230285-11-7 5-(tert-butyldiphenylsiloxy)-1-phenyl-1-pentanone 

Downstream Products

• 73464-88-7 (R)-2-phenyl-hexan-2-ol 
• 19641-54-4 (S)-2-phenyl-hexan-2-ol 

Relevant academic research and scientific papers

Inter- and intramolecular pathways for the formation of tetrahydrofurans from β-(phosphatoxy)alkyl radicals. Evidence for a dissociative mechanism

β-(Phosphatoxy)alkyl radicals generated by photolysis of Barton PTOC esters in the presence of allyl alcohol and tert-butyl mercaptan undergo nucleophilic substitution followed by 5-exo-trig radical ring closure leading to tetrahydrofurans in good yield and with high trans selectivity. β- (Phosphatoxy)alkyl radicals obtained by intramolecular hydrogen 1,5- abstraction with an alkoxyl radical undergo nucleophilic displacement providing tetrahydrofurans. The ensemble of results, including the effects of leaving groups and substituents, strongly support a dissociative mechanism for these radical nucleophilic displacement reactions.

Arene-catalysed reductive lithiation of tetrahydrofuran: Improved synthesis of 1,5-diols

The reductive cleavage of tetrahydrofuran at -78°C can be easily achieved by using an excess of lithium powder in the presence of BF3-·OEt2 and a catalytic amount (8%) of an arene (naphthalene, biphenyl, 4,4'-di-tert-butylbiphenyl or anthracene), the best results being obtained with naphthalene. The dianion prepared by this method reacts with carbonyl compounds yielding 1,5-diols.