1-(1,3-benzothiazol-2-yl)-2,2,2-trifluoroethanone

Base Information

• Chemical Name: 1-(1,3-benzothiazol-2-yl)-2,2,2-trifluoroethanone
• CAS No.: 929973-34-2
• Molecular Formula: C₉H₄F₃NOS
• Molecular Weight: 231.198

Synonyms:1-(1,3-benzothiazol-2-yl)-2,2,2-trifluoroethanone

Chemical Property of 1-(1,3-benzothiazol-2-yl)-2,2,2-trifluoroethanone

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

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• General Description: 1-(1,3-Benzothiazol-2-yl)-2,2,2-trifluoroethanone (also referred to as 2-trifluoroacetyl-1,3-benzothiazole) is a key reagent in the electrophilic oxyalkylation of anilines, enabling the synthesis of trifluoromethyl-substituted alcohols. Its reactivity with various anilines under mild heating conditions demonstrates high regioselectivity, particularly influenced by the substitution pattern of the aniline, leading to products with ortho/para-selectivity in good to excellent yields. 1-(1,3-benzothiazol-2-yl)-2,2,2-trifluoroethanone serves as an effective electrophile in this transformation, facilitating the introduction of a trifluoromethyl alcohol moiety into aromatic systems.

Refernces

Noncatalytic electrophilic oxyalkylation of anilines with 2-trifluoroacetyl-1,3-benzothiazole

10.1055/s-0029-1218712

The research focuses on the noncatalytic electrophilic oxyalkylation of anilines with 2-trifluoroacetyl-1,3-benzothiazole, aiming to form trifluoromethyl-substituted alcohols. The study investigates the reaction's regioselectivity, which is found to be highly dependent on the structure of the aniline used. Various substituted anilines (compounds 2–18) were reacted with 2-trifluoroacetyl-1,3-benzothiazole (1a) under heating in toluene at 60–100 °C for 0.5–4 hours, yielding the desired trifluoromethyl alcohols 2a–18a in 25–99% yields. The reactions' outcomes were analyzed using 1H NMR, 13C NMR, 19F NMR, and APSI MS to determine the structures and confirm the formation of the products, with particular attention to the ortho/para-substitution patterns influenced by the meta-substituents on the aniline reactants.

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