Chemistry:2,4,6-Trichlorobenzoyl chloride

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2,4,6-Trichlorobenzoyl chloride
2,4,6-Trichlorobenzoyl chloride.png
Names
IUPAC name
2,4,6-trichlorobenzoyl chloride
Other names
Yamaguchi's reagent
Identifiers
3D model (JSmol)
Abbreviations TCBC
2050280
ChemSpider
EC Number
  • 609-916-0
UNII
UN number 3265
Properties
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)
Reacts with water
log P 2.738
Hazards
GHS pictograms GHS05: Corrosive
GHS Signal word Danger
H314
P264, P280, P301+330+331, P303+361+353, P304+340+310, P305+351+338+310, P363, P405, P501
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity (yellow): no hazard codeSpecial hazards (white): no codeNFPA 704 four-colored diamond
0
3
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.

Yamaguchi lactonization.svg

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]

Preparation of 2,4,6-trichlorobenzoyl chloride.png

Since 2,4,6-trichlorobenzoic acid is produced as a by product of the esterification process, it can be refluxed again to recreate 2,4,6-trichlorobenzoyl chloride.

References

  1. ↑ "2,4,6-Trichlorobenzoyl chloride" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/2733703#section=Safety-and-Hazards. 
  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" (in en). Chem. Commun. (29): 3045–3047. doi:10.1039/B707835H. ISSN 1359-7345. PMID 17639136. http://xlink.rsc.org/?DOI=B707835H. 
  3. ↑ Panek, J. S., ed (2007) (in en). 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. http://www.thieme-connect.de/DOI/DOI?10.1055/b-003-125722. [yes|permanent dead link|dead link}}]
  4. ↑ Kotammagari, Tharun (2014-04-28). "2,4,6-Trichlorobenzoyl Chloride (Yamaguchi Reagent)" (in en). Synlett 25 (9): 1335–1336. doi:10.1055/s-0033-1341245. ISSN 0936-5214. 




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