2,4,6-Trichlorobenzoyl chloride

2,4,6-Trichlorobenzoyl chloride 2,4,6-Trichlorobenzoyl chloride.svg 2,4,6-Trichlorobenzoyl chloride Yamaguchi's reagent TCBC 4136-95-2 correct CAS 2733703 2015479 609-916-0 3265 C1=C(C=C(C(=C1Cl)C(=O)Cl)Cl)Cl 1S/C7H2Cl4O/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2H OZGSEIVTQLXWRO-UHFFFAOYSA-N 2050280 1083Y98L1D 7 2 4 1 Light yellow liquid 1.561 g/mL 107 - 108 °C (225 - 226 °F) 2.738 Reacts with water 2,4,6-Trichlorobenzoyl chloride https://pubchem.ncbi.nlm.nih.gov/compound/2733703#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov 7 April 2022 en 05 Danger 314 264 280 301+330+331 303+361+353 304+340+310 305+351+338+310 363 405 501 3 0 0 113 °C 2,4,6-Trichlorobenzoyl chloride or Yamaguchi's reagent is an chlorinated aromatic compound that is commonly used in a variety of organic syntheses.Fürstner Alois Fasching Bernhard O'Neil Gregory W. Fenster Michaël D. B. Godbout Cédrickx Ceccon Julien 2007 Toward the total synthesis of spirastrellolide A. Part 3: Intelligence gathering and preparation of a ring-expanded analogue http://xlink.rsc.org/?DOI=B707835H Chem. Commun. en 29 3045–3047 10.1039/B707835H 17639136 1359-7345 subscription http://www.thieme-connect.de/DOI/DOI?10.1055/b-003-125722 Category 3, Compounds with Four and Three Carbon Heteroatom Bonds: Three Carbon—Heteroatom Bonds: Esters, and Lactones; Peroxy Acids and R(CO)OX Compounds; R(CO)X, X=S, Se, Te 2007 Georg Thieme Verlag 978-3-13-144691-6 Panek J. S. Stuttgart en 10.1055/sos-sd-020-01369 Yamaguchi esterification It is the primary reactant in Yamaguchi esterification. 2,4,6-Trichlorobenzoyl chloride readily reacts with alcohols. This newly formed reagent, when mixed with a stoichiometric amount of 4-dimethylaminopyridine, cyclizes and forms esters. This reaction creates 2,4,6-trichlorobenzoic acid as a byproduct. center|frameless|482x482px Preparation 2,4,6-Trichlorobenzoyl chloride is prepared by reacting 2,4,6-trichloroaniline with n-butyllithium in a carbon dioxide atmosphere. This produces 2,4,6-trichlorobenzoic acid, which can then be refluxed in thionyl chloride to form 2,4,6-trichlorobenzoyl chloride.Kotammagari Tharun 2014-04-28 2,4,6-Trichlorobenzoyl Chloride (Yamaguchi Reagent) Synlett en 25 9 1335–1336 10.1055/s-0033-1341245 0936-5214 free center|frameless|390x390px Since 2,4,6-trichlorobenzoic acid is produced as a by product of the Yamaguchi esterification process, it can be refluxed again to recreate 2,4,6-trichlorobenzoyl chloride. References Category:Chlorobenzene derivatives Category:Acyl chlorides Category:Reagents for organic chemistry