2,4,6-trichlorobenzoyl chloride

• ChemBase ID: 89261
• Molecular Formular: C7H2Cl4O
• Molecular Mass: 243.90218
• Monoisotopic Mass: 241.8859754
• SMILES: O=C(c1c(cc(cc1Cl)Cl)Cl)Cl
• Canonical SMILES: Clc1cc(Cl)c(c(c1)Cl)C(=O)Cl
• InChI: InChI=1S/C7H2Cl4O/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2H
• InChIKey: OZGSEIVTQLXWRO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,4,6-trichlorobenzoyl chloride
• IUPAC Traditional name: 2,4,6-trichlorobenzoyl chloride
• Synonyms: 2,4,6-Trichlorobenzoyl chloride; 2,4,6-Trichlorobenzoyl chloride; 2,4,6-三氯苯甲酰氯

Database IDs

• CAS Number: 4136-95-2
• MDL Number: MFCD00075323
• Beilstein Number: 2050280
• PubChem SID: 162076143; 24861329
• PubChem CID: 2733703

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.9762924
• LogD (pH = 7.4): 3.9762924
• Log P: 3.9762924
• Molar Refractivity: 51.5871 cm^3
• Polarizability: 19.974146 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 107-108 °C/6 mmHg(lit.); 107-108°C/6mm; 107-108°C/6mm
• Flash Point: >110°C(230°F); 113 °C; 113°C; 235.4 °F
• Density: 1.561; 1.561 g/mL at 25 °C(lit.)
• Refractive Index: 1.5750; 1.5754; n20/D 1.5754(lit.)

Safety Information

• Storage Warning: Corrosive/Lachrymatory/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3265; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 20-26-36/37/39-45; 26-27-28-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 2

Product Information

• Purity: 97%; 98%
• Linear Formula: Cl3C6H2COCl

DETAILS

Sigma Aldrich - 345504

Packaging
5 g in glass bottle
Application
Useful for the preparation of large-ring lactones in high yields.1

REFERENCES

• Reagent, introduced by Yamaguchi, which forms mixed anhydrides with acids, useful in the synthesis of esters: Bull. Chem. Soc. Jpn., 52, 1989 (1979), or lactones including macrolides: Chem. Lett., 1021 (1979). Superior to mesitylenesulfonyl chloride for macrolactonization, which has been achieved in the presence of DMAP without the need for high dilution: J. Org. Chem., 55, 7 (1990); Tetrahedron Lett., 31, 6367 (1990).