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345504

Sigma-Aldrich

2,4,6-Trichlorobenzoyl chloride

97%

Synonym(s):

2,4,6-Trichlorobenzoyl chloride

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About This Item

Linear Formula:
Cl3C6H2COCl
CAS Number:
4136-95-2
Molecular Weight:
243.90
MDL number:
MFCD00075323
UNSPSC Code:
12352100
PubChem Substance ID:
24861329
NACRES:
NA.22

Quality Level

200

Assay

97%

form

liquid

refractive index

n20/D 1.5754 (lit.)

bp

107-108 °C/6 mmHg (lit.)

density

1.561 g/mL at 25 °C (lit.)

SMILES string

ClC(=O)c1c(Cl)cc(Cl)cc1Cl

InChI

1S/C7H2Cl4O/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2H

InChI key

OZGSEIVTQLXWRO-UHFFFAOYSA-N

Application

2,4,6-Trichlorobenzoyl chloride may be used in the preparation of:
  • γ-lactone and δ-lactone
  • aliphatic aromatic anhydrides, required for the synthesis of amphiphilic hyaluronan
  • mixed anhydride, required for the synthesis of angelate esters
  • synthesis of both spongistatin 1 and spongistatin 2
  • large-ring lactones in high yields.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

T74802

2,4,6-Trimethylbenzoic acid

Improved preparation of angelate esters.
Hartmann B, et al.
Tetrahedron Letters, 32(38), 5077-5080 (1991)
Fieser, M.
Reagents for Organic Synthesis, 16, 353-353 (1992)
Machiko Ono et al.
Chemical & pharmaceutical bulletin, 61(4), 464-470 (2013-04-03)
Alkaline hydrolysis of 4-hydroxy- or/and 5-hydroxy-(2E)-alkenoate followed by acid treatment gave the corresponding (2E)-alkenoic acids which were subjected to lactone formation reaction without further purification. The crude acids were treated with 2,4,6-trichlorobenzoyl chloride in pyridine to afford γ-lactone or δ-lactone
Michael T Crimmins et al.
Journal of the American Chemical Society, 124(20), 5661-5663 (2002-05-16)
The total synthesis of spongistatin 1 (1) and spongistatin 2 (2) has been achieved through an advanced-stage intermediate. The synthesis is highlighted by a highly convergent assembly of the four key fragments (the C1-C15 AB fragment 2, the C16-C28 CD
Gloria Huerta-Angeles et al.
Carbohydrate polymers, 111, 883-891 (2014-07-20)
The present work describes a novel and efficient method of synthesis of amphiphilic hyaluronan (HA) by esterification with alkyl fatty acids. These derivatives were synthesized under mild aqueous and well controlled conditions using mixed aliphatic aromatic anhydrides. These anhydrides characterized

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