en 2,4,6-Trichlorobenzoyl chloride

2,4,6-Trichlorobenzoyl chloride
Names
	IUPAC name 2,4,6-trichlorobenzoyl chloride
	Other names Yamaguchi's reagent
Identifiers
CAS Number	4136-95-2 ;
3D model (JSmol)	Interactive image;
Abbreviations	TCBC
Beilstein Reference	2050280
ChemSpider	2015479;
ECHA InfoCard	100.120.466
EC Number	609-916-0;
PubChem CID	2733703;
UNII	1083Y98L1D;
UN number	3265
CompTox Dashboard (EPA)	DTXSID80369980 ;
	InChI InChI=1S/C7H2Cl4O/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2H Key: OZGSEIVTQLXWRO-UHFFFAOYSA-N;
	SMILES C1=C(C=C(C(=C1Cl)C(=O)Cl)Cl)Cl;
Properties
Chemical formula	C7H2Cl4O
Molar mass	243.89 g·mol−1
Appearance	Light yellow liquid
Density	1.561 g/mL
Boiling point	107 - 108 °C (225 - 226 °F)
Solubility in water	Reacts with water
log P	2.738
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	P264, P280, P301+P330+P331, P303+P361+P353, P304+P340+P310, P305+P351+P338+P310, P363, P405, P501
NFPA 704 (fire diamond)	3 0 0
Flash point	113 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2,4,6-Trichlorobenzoyl chloride or Yamaguchi's reagent is an chlorinated aromatic compound that is commonly used in a variety of organic syntheses.^[2]^[3]

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.

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.^[4]

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

^ "2,4,6-Trichlorobenzoyl chloride". pubchem.ncbi.nlm.nih.gov. Retrieved 7 April 2022.
^ 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". Chem. Commun. (29): 3045–3047. doi:10.1039/B707835H. ISSN 1359-7345. PMID 17639136.
^ Panek, J. S., ed. (2007). 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. Stuttgart: Georg Thieme Verlag. doi:10.1055/sos-sd-020-01369. ISBN 978-3-13-144691-6.
^ Kotammagari, Tharun (2014-04-28). "2,4,6-Trichlorobenzoyl Chloride (Yamaguchi Reagent)". Synlett. 25 (9): 1335–1336. doi:10.1055/s-0033-1341245. ISSN 0936-5214.

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[1] "2,4,6-Trichlorobenzoyl chloride". pubchem.ncbi.nlm.nih.gov. Retrieved 7 April 2022.

[2] 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". Chem. Commun. (29): 3045–3047. doi:10.1039/B707835H. ISSN 1359-7345. PMID 17639136.

[3] Panek, J. S., ed. (2007). 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. Stuttgart: Georg Thieme Verlag. doi:10.1055/sos-sd-020-01369. ISBN 978-3-13-144691-6.

[4] Kotammagari, Tharun (2014-04-28). "2,4,6-Trichlorobenzoyl Chloride (Yamaguchi Reagent)". Synlett. 25 (9): 1335–1336. doi:10.1055/s-0033-1341245. ISSN 0936-5214.

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