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2,4,6-Trichlorobenzoyl Chloride
(CAS RN:4136-95-2 Product Number:T1413)

Structure

2,4,6-Trichlorobenzoyl Chloride

General Information

Product Number T1413

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Purity/Analysis Method >98.0%(GC)(T)
Storage Temperature
M.F. / M.W. C7H2Cl4O=243.89
CAS RN 4136-95-2
Related CAS RN
MDL Number MFCD00075323
Packaging and Container
  • Product Details
  • Safety & Regulations

Specification

Appearance Colorless to Light yellow clear liquid
Purity(GC) min. 98.0 %
Purity(Argentmetric Titration) min. 98.0 %

Data of Reference

bp 275°C(lit.)

References

Beilstein 9,346
Reaxys-RN 2050280
PubChem SID 87577179
F&F 11,552

GHS

Pictogram
Signal Word Danger
Hazard Statements
  • H290
  • :May be corrosive to metals.
  • H314
  • :Causes severe skin burns and eye damage.
Precautionary Statements
  • P260
  • :Do not breathe dusts or mists.
  • P280
  • :Wear protective gloves, protective clothing, face protection.
  • P301+P330+P331+P310
  • :IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Immediately call a POISON CENTER or doctor.
  • P303+P361+P353+P310+P363
  • :IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water or shower. Immediately call a POISON CENTER or doctor. Wash contaminated clothing before reuse.
  • P304+P340+P310
  • :IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER or doctor.
  • P305+P351+P338+P310
  • :IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor.

Transport Information

UN Number 3265
Class 8
Packing Group II
HS Number 2916399090

Application

Yamaguchi Esterification and Macrolactonization

2,4,6-Trichlorobenzoyl chloride is often used for the Yamaguchi esterification and macrolactonization. The Yamaguchi esterification is the rapid and mild esterification method in the presence of 4-dimethylaminopyridine (DMAP) using a mixed anhydride, which is prepared from 2,4,6-trichlorobenzoyl chloride and the carboxylic acid. 1–3) The features of this esterification are as follows: 1) the reaction is conducted under high-dilution conditions to minimize intermolecular coupling; 2) the mixed anhydride is dissolved and slowly added to a refluxing solution of DMAP in aromatic hydrocarbons (e.g. benzene, toluene); 3) usually several equivalents of DMAP, as a catalyst for acylation, are used. It is especially useful in the synthesis of macrolactones with intramolecular esterification, called the Yamaguchi macrolactonization. 1,4)
Typical procedure1): A mixture of the seco acid (272 mg) and triethylamine (153 μL) in THF (10 mL) is stirred for 10 min at room temperature, and then 2,4,6-trichlorobenzoyl chloride (160 μL) is added. After stirring for 2 h at room temperature, the resulting precipitate is filtered and washed with a small amount of THF. The filtrate is diluted with benzene (500 mL) and slowly added to a refluxing solution of DMAP (732 mg) in benzene (100 mL) over a period of 40 h. The reaction mixture is washed successively with a saturated aqueous citric acid solution, water, an aqueous sodium hydrogen carbonate, and water, and dried over anhydrous magnesium sulfate. Concentration of the filtrate under reduced pressure affords a crude product. The product is separated by preparative TLC (eluent: diethyl ether / benzene = 2 / 1) on silica gel to give 116 mg of the lactone (46 % yield).

References

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