58041-01-3

Usage

Physical State

Yellowish liquid

Odor

Pungent

Primary Use

Building block for synthesizing organic compounds in research and experimental applications

Classification

Alpha,beta-unsaturated aldehyde

Environmental Impact

Potential environmental contaminant

Toxicity

Implicated in various toxicological and biochemical processes

Safety Considerations

Handle with caution due to potential risks to human health and safety

Upstream product

• 139680-72-1 1,1,5,5-tetraethyl-1,5-diaza-3-fluoro-2,4-pentadienium iodide 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 624-31-7 4-tolyl iodide 
• 152873-64-8 (2Z)-3-(diethylamino)-2-fluoroprop-2-enal 

Relevant academic research and scientific papers

Montmorillonite K 10 (clay) catalyzed hydrolysis of aryl-substituted α,β-difluoroallyl alcohols leading to (Z)-α-fluoro-β-aryl-substituted acrylaldehydes

Aryl-substituted aα,β-difluoroallyl alcohols 1 were readily hydrolyzed in the presence of a catalytic amount of montmorillonite K 10 (clay) in hexane at reflux temperature for 1 h to give the corresponding (Z)-α- fluoro-β-aryl-substituted acrylaldehydes 2

Reaction of β-fluorovinamidinium salt with grignard reagents. Facile and efficient route to (Z)-α-fluoro-α,β-unsaturated aldehydes

β-Fluorovinamidinium salt (1) reacted cleanly with a variety of Grignard reagents in tetrahydrofuran at room temperature, followed by acid workup, to produce the corresponding (Z)-α-fluoro-α,β-unsaturated aldehydes (3) in good to excellent yields.

An efficient and general entry to (Z)-α-fluoro-β-substituted acrylaldehydes based on the coupling reaction of α-fluoro-β-amino acrylaldehydes with organolithium reagents

α-Fluoro-β-amino acrylaldehydes (2), readily available from the reaction of polyfluoroalkenyl tosylates (1) with dialkylamines in the presence of triethylamine and a catalytic amount (10 mol%) of tetrabutylammonium fluoride (TBAF), reacted smoothly with various organolithium reagents at -78 °C for 0.5 h, followed by hydrolysis with 10% hydrochloric acid at room temperture for 1 h to afford the corresponding (Z)-α-fluoro-β-substituted acrylaldehydes (3) via allylic rearrangement in good to excellent yields.