CAS 4136-95-2, Cat. No EN300-316966
Reagent for esterification and macrolactonization
2,4,6-Trichlorobenzoyl chloride (TCBCl), commonly named the Yamaguchi reagent, is a versatile organic synthesis tool, specifically designed for soft esterification and macrolactonization reactions1. It is a light-yellow moisture-sensitivity liquid2. Similar to other highly reactive acid chlorides, the reaction procedure with TCBCl is straightforward and intuitive. The Yamaguchi reagent is an excellent choice for challenging substrates encountered in medicinal chemistry and other complex synthetic scenarios. Its utility extends to the total synthesis of natural products that feature a macrolactone motif, as evidenced by its successful application in numerous such syntheses.
Synonyms: 2,4,6-trichlorobenzoyl chloride; benzoyl chloride, 2,4,6-trichloro-; TCBCl; Yamaguchi reagent
Selected publications
-
A Rapid Esterification by Means of Mixed Anhydride and Its Application to Large-Ring Lactonization.
Inanaga J.; Hirata K.; Saeki H.; Katsuki T.; Yamaguchi M. Bull Chem Soc Jpn 1979, 52 (7), 1989–1993. DOI: 10.1246/bcsj.52.1989
-
2,4,6-Trichlorobenzoyl Chloride.
Ewin R.; Pertusati F. Encyclopedia of Reagents for Organic Synthesis 2013. DOI: 10.1002/047084289X.rt201.pub2