Trichlorobenzoic acid

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Trichlorobenzoic acids (TBAs) are organochlorine compounds, in particular benzoic acids, with the formula C6H2Cl3CO2H. Six constitutional isomers exist, differing in the relative position of the three chlorine substituents around the ring.

Contents

Trichlorobenzoic acids
Name2,3,4-Trichlorobenzoic acid2,3,5-Trichlorobenzoic acid 2,3,6-Trichlorobenzoic acid 2,4,5-Trichlorobenzoic acid2,4,6-Trichlorobenzoic acid3,4,5-Trichlorobenzoic acid
Structure 2,3,4-Trichlorobenzoic acid.png 2,3,5-Trichlorobenzoic acid.png 2,3,6-Trichlorobenzoic acid.png 2,4,5-Trichlorobenzoic acid.png 2,4,6-Trichlorobenzoic acid.png 3,4,5-Trichlorobenzoic acid.png
CAS Registry Number [50-75-9][50-73-7][50-31-7][50-82-8][50-43-1][51-39-8]

Preparation and use

The 2,4,6- isomer is easily produced by deprotonation of 1,3,5-trichlorobenzene followed by reaction with carbon dioxide. [1] Its conversion to 2,4,6-trichlorobenzoyl chloride makes it a key intermediate in the Yamaguchi esterification protocol.

Related Research Articles

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<span class="mw-page-title-main">Triazine</span> Aromatic, heterocyclic compound

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<span class="mw-page-title-main">Phloroglucinol</span> Chemical compound

Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed polyphenols.

<span class="mw-page-title-main">Maleic acid</span> Dicarboxylic acid

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1,3,5-Triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. s-Triazine —the "symmetric" isomer—and its derivatives are useful in a variety of applications.

<span class="mw-page-title-main">Levopropoxyphene</span> Chemical compound

Levopropoxyphene is an antitussive. It is an optical isomer of dextropropoxyphene. The racemic mixture is called propoxyphene. Only the dextro-isomer (dextropropoxyphene) has an analgesic effect; the levo-isomer appears to exert only an antitussive effect. It was formerly marketed in the U.S. by Eli Lilly under the tradename Novrad as an antitussive. Unlike many antitussives, it binds poorly to the sigma-1 receptor.

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<span class="mw-page-title-main">2,4,6-Trichlorophenol</span> Chemical compound

2,4,6-Trichlorophenol, also known as TCP, phenaclor, Dowicide 2S, Dowcide 2S, omal, is a chlorinated phenol that has been used as a fungicide, herbicide, insecticide, antiseptic, defoliant, and glue preservative. It is a clear to yellowish crystalline solid with a strong, phenolic odor. It decomposes on heating to produce toxic and corrosive fumes including hydrogen chloride and chlorine.

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The Yamaguchi esterification is the chemical reaction of an aliphatic carboxylic acid and 2,4,6-trichlorobenzoyl chloride to form a mixed anhydride which, upon reaction with an alcohol in the presence of stoichiometric amount of DMAP, produces the desired ester. It was first reported by Masaru Yamaguchi et al. in 1979.

<i>cis</i>-Dichlorobis(ethylenediamine)cobalt(III) chloride Chemical compound

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<span class="mw-page-title-main">Humulone</span> Chemical compound

Humulone, a vinylogous type of organic acid, is a bitter-tasting chemical compound found in the resin of mature hops. Humulone is a prevalent member of the class of compounds known as alpha acids, which collectively give hopped beer its characteristic bitter flavor.

<span class="mw-page-title-main">Diphosphene</span> Chemical compound

Diphosphene is a compound having the formula (PH)2. It exists as two geometric isomers, E and Z. Diphosphene is also the parent member of the entire class of diphosphene compounds with the formula (PR)2, where R is an organyl group.

<span class="mw-page-title-main">Cyclononatetraene</span> Chemical compound

Cyclononatetraene is an organic compound with the formula C9H10. It was first prepared in 1969 by protonation of the corresponding aromatic anion (described below). It is unstable and isomerizes with a half-life of 50 minutes at room temperature to 3a,7a-dihydro-1H-indene via a thermal 6π disrotatory electrocyclic ring closing. Upon exposure to ultraviolet light, it undergoes a photochemical 8π electrocyclic ring closing to give bicyclo[6.1.0]nona-2,4,6-triene.

<span class="mw-page-title-main">2,4,6-Trimethylpyridine</span> Chemical compound

2,4,6-Trimethylpyridine (2,4,6-collidine) is an organic compound which belongs to the heterocycles. It consists of a pyridine ring substituted with three methyl groups. It belongs to the substance group of the collidines, a group of six constitutional isomers. 2,4,6-trimethylpyridine is the most well-known isomer of this group.

Trichlorotoluenes are organochlorine compounds, in particular aryl chlorides, with the formula CH3C6H2Cl3. Six constitutional isomers exist, differing in the relative position of the three chlorine substituents around the ring. All isomers colorless and lipophilic solids.

<span class="mw-page-title-main">Mesitol</span> Chemical compound

Mesitol (2,4,6-trimethylphenol) is an organic compound with the formula (CH3)3C6H2OH. It is one of several isomers of trimethylphenol. The name and structure of mesitol derives from the combination of mesitylene and phenol.

Pyridinetricarboxylic acid is a group of organic compounds which are tricarboxylic derivatives of pyridine. Pyridinetricarboxylic acid comes in several isomers:

<span class="mw-page-title-main">2,4,6-Trichlorobenzoyl chloride</span> Chemical compound

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

References

  1. 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.