2,4,6-trichlorobenzoyl chloride

EN300-316966

Product class

Building Blocks

CAS number

4136-95-2

MW

243.90

Purity

95%

Lead time

from 7 days delivery time

Reagent for esterification and macrolactonization

2,4,6-trichlorobenzoyl chloride (TCBCl), commonly referred to as the Yamaguchi reagent, is a versatile tool in organic synthesis, specifically designed for soft esterification and macrolactonization reactions[1]. This light yellow liquid exhibits sensitivity to moisture[2]. Similar to other highly reactive acid chlorides, the reaction procedure with TCBCl is straightforward and intuitive. The Yamaguchi reagent proves to be 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; TCBCl

1. 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. 2,4,6-Trichlorobenzoyl Chloride. Ewin R. A.; Pertusati F. Encyclopedia of Reagents for Organic Synthesis 2013. DOI: 10.1002/047084289X.rt201.pub2

Name:

2,4,6-trichlorobenzoyl chloride

SMILES:

O=C(Cl)C=1C(Cl)=CC(Cl)=CC1Cl

CAS number:

4136-95-2

CLogP:

3.705

ACD number:

MFCD00075323

Dangerous good:

Yes

Class:

Acyl Halides

Formula:

C₇H₂Cl₄O

Subclass:

Acyl Halides

MW:

243.90

Product class:

Building Blocks