902757-39-5

Basic information

• Product Name: N-(isopropoxy)-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione
• Synonyms: N-(isopropoxy)-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione
• CAS NO: 902757-39-5
• Molecular Weight: 295.426
• Mol File: 902757-39-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(isopropoxy)-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione(CAS DataBase Reference)
• NIST Chemistry Reference: N-(isopropoxy)-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione(902757-39-5)
• EPA Substance Registry System: N-(isopropoxy)-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione(902757-39-5)

Safety Data

• Hazardous Substances Data: 902757-39-5(Hazardous Substances Data)

Upstream product

• 2307-69-9 toluene-4-sulfonic acid isopropyl ester 

Relevant articles and documents

Aspects of structural thiohydroxamate chemistry-on a systematic in the 5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione series

Bond angles at thiohydroxamate oxygen in crystal structures of 3-alkoxy-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thiones gradually increased with the size of the 3-alkoxy substituent. This effect was attributed to strain on the basis of (i) a linear free energy relationship (Taft-Dubois correlation) and (ii) signal coalescence from resonances of diastereotopic CH3 groups in solution (O-cumyl substituent; DNMR). Substitution at oxygen along the sequence OR (R=prim-, sec-, and tert-alkyl), OH, and OLi was reflected in a gradual decrease of N,O distances and lengthening of associated C,S bonds. The responsivity for these changes was more pronounced in the thiazole-2(3H)-thione than in the pyridine-2(1H)-thione series.

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.