195213-59-3

Basic information

• Product Name: 2(3H)-Thiazolethione, 4-(4-chlorophenyl)-3-[(2-phenyl-4-pentenyl)oxy]-
• CAS NO: 195213-59-3
• Molecular Formula: C20H18ClNOS2
• Molecular Weight: 387.954
• Mol File: 195213-59-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2(3H)-Thiazolethione, 4-(4-chlorophenyl)-3-[(2-phenyl-4-pentenyl)oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Thiazolethione, 4-(4-chlorophenyl)-3-[(2-phenyl-4-pentenyl)oxy]-(195213-59-3)
• EPA Substance Registry System: 2(3H)-Thiazolethione, 4-(4-chlorophenyl)-3-[(2-phenyl-4-pentenyl)oxy]-(195213-59-3)

Safety Data

• Hazardous Substances Data: 195213-59-3(Hazardous Substances Data)

Upstream product

• 182194-86-1 2-phenyl-4-penten-1-yl p-toluenesulfonate 

Downstream Products

• 24401-36-3 2-phenyl-4-penten-1-al 
• 130284-35-4 2-phenyl-pent-4-en-1-ol 
• 85268-00-4 2-(bromomethyl)-4-phenyltetrahydrofuran 
• 227082-35-1 2-(tributylstannyl)sulfanyl-4-(p-chlorophenyl)thiazole 

Relevant articles and documents

Microwave-assisted generation of alkoxyl radicals and their use in additions, β-fragmentations, and remote functionalizations

Microwave irradiation (2.45 GHz, 300-500 W) of N-(alkoxy)thiazole-2(3H)- thiones in low-absorbing solvents affords alkoxyl radicals, which were identified by (i) spin adduct formation (EPR-spectroscopy) and (ii) fingerprint-type selectivities in intramolecular additions (stereoselective synthesis of disubstituted tetrahydrofurans), β-fragmentations (formation of carbonyl compounds), and C,H-activation of aliphatic subunits, by δ-selective hydrogen atom transfer. C-Radicals formed from oxygen-centered intermediates were trapped either by Bu3SnH, l-cysteine ethyl ester, the reduced form of glutathione (reductive trapping), or by bromine atom donor BrCCl3 (heteroatom functionalization) The results suggest that microwave activation is superior to UV/Vis-photolysis and conductive heating for alkoxyl radical generation from N-(alkoxy)thiazolethiones. It offers by far the shortest reaction times along with the option to reduce the amount of trapping reagent significantly. The Royal Society of Chemistry 2006.

Towards Improved Alkoxyl Radical Precursors - The Synthesis of N-Alkoxy-4-(p-chlorophenyl)thiazole-2(3H)-thiones

4-(p-Chlorophenyl)-3-hydroxythiazol-2(3H)-thione (3) can be prepared in good yields and in useful quantities from p-chloro acetophenone (1). O-Alkylation of the cyclic thiohydroxamic acid 3 via the respective potassium or the tetraethyl ammonium salts affords the esters 4. A slightly modified procedure allows the conversion of the acid 3 to the mixed anhydrides 5. The esters 4 and the anhydrides 5 are colorless to yellowish crystalline compounds which show a good shelf life. Visible light photolysis of the N-alkoxy derivatives 4e-g and reactive hydrogen donors affords substituted tetrahydrofurans 7 or tetrahydropyrans 8 via an alkoxyl radical pathway.