24536-68-3

Usage

Physical state

Pale yellow liquid

Boiling point

267-269 degrees Celsius

Flash point

107 degrees Celsius

Usage

Synthesis of pharmaceuticals, raw material in organic chemical production, flavor and fragrance ingredient in perfumes and other consumer products

Natural occurrence

Found in some natural sources

Potential applications

Organic chemistry and drug development.

Upstream product

• 25501-32-0 (S)-indanol 
• 821784-98-9 N,N-diisopropyl O-[(S)-3-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)]prop-1-yl carbamate 
• 172-16-7 indanone dithioacetal 

Relevant academic research and scientific papers

Stereospecific Synthesis of Alkenes by Eliminative Cross-Coupling of Enantioenriched sp3-Hybridized Carbenoids

1-Aryl-1,2-dialkylethenes were generated by a sequence of electrophilic substitution, 1,2-metalate rearrangement, and β-elimination initiated by the addition of enantioenriched α-(carbamoyloxy)alkylboronates to enantioenriched lithiated carbamates. The carbenoid stereochemical pairing [i.e., “like”=(S)+(S) or “unlike”=(S)+(R)] and the elimination mechanism (syn or anti), not substituent effects, determined the configuration of the trisubstituted alkene target. For example, (Z)-2,5-diphenyl-2-pentene was produced in 70 % yield with E/Z=5:95 by a like combination of Li and B carbenoids and syn (thermal) elimination whereas the E isomer was obtained in the same yield with E/Z>98:2 by an otherwise identical process involving an unlike stereochemical pairing. The concept elaborated overcomes an intrinsic limitation of traditional strategies for direct connective alkene synthesis, which cannot realize meaningful stereochemical bias unless the alkene substituents are strongly differentiated.

W(CO)6-Mediated Desulfurdimerization of Dithioketals. Evidence for a Thione Intermediate

Upon treatment with W(CO)6, dithioketals undergo desulfurdimerization to give the corresponding dimeric olefins in good to excellent yields.The mechanism of this the newly discovered reaction has been investigated.Thioketones have been isolated from the reactions of highly crowded dithioketals.The mechanism for the formation of thioketones has been shown to occur via a new type of radical fragmentation process of dithiolane.Thermolysis of 2,2-dimethylindan-1-yl 2-thiophenoxyethyl sulfide in the presence of tert-butyl adamantane-1-peroxycarboxylate (a typical radical initiator) has been studied for comparison.Thioketones react with W(CO)6, giving dimeric olefins and/or undergoing carbene-like insertion reactions.