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391794

Sigma-Aldrich

1,1′-(4,6-Dihydroxy-1,3-phenylene)bisethanone

99%

Synonym(s):

4,6-Diacetylresorcinol

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About This Item

Linear Formula:
(HO)2C6H2(COCH3)2
CAS Number:
2161-85-5
Molecular Weight:
194.18
EC Number:
218-482-8
MDL number:
MFCD00017655
UNSPSC Code:
12352100
PubChem Substance ID:
24864402
NACRES:
NA.22

Quality Level

100

Assay

99%

mp

178-180 °C (lit.)

SMILES string

CC(=O)c1cc(C(C)=O)c(O)cc1O

InChI

1S/C10H10O4/c1-5(11)7-3-8(6(2)12)10(14)4-9(7)13/h3-4,13-14H,1-2H3

InChI key

GEYCQLIOGQPPFM-UHFFFAOYSA-N

General description

1,1′-(4,6-Dihydroxy-1,3-phenylene)bisethanone (4,6-diacetylresorcinol, DAR) is a bifunctional carbonyl compound. Its synthesis by acetylating resorcinol in the presence of zinc chloride has been reported. The crystal structure of DAR has been studied.

Application

1,1′-(4,6-Dihydroxy-1,3-phenylene)bisethanone (4,6-diacetylresorcinol, DAR) may be used in the synthesis of the following:
  • Schiff base ligands
  • hexadentate chalcogenated bisimine ligands
  • 1,5-benzodiazepines
  • ketimine of chitosan
  • mannich bases
  • hydrazone ligands
  • thiosemicarbazone, semicarbazone and thiocarbohydrazone ligands
  • binuclear cobalt(II) and copper(II) complexes
  • europium (III) complexes

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Magdy Shebl
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 70(4), 850-859 (2007-11-13)
A tetradentate N2O2 donor Schiff base ligand, H2L, was synthesized by the condensation of 4,6-diacetylresorcinol with benzylamine. The structure of the ligand was elucidated by elemental analyses, IR, 1H NMR, electronic and mass spectra. Reaction of the Schiff base ligand
Spectral characterization and biological evaluation of Schiff bases and their mixed ligand metal complexes derived from 4, 6-diacetylresorcinol.
Pandya JH, et al.
Journal of Saudi Chemical Society, 18(3), 190-199 (2011)
Arun Kumar et al.
Journal of hazardous materials, 269, 9-17 (2013-12-10)
Potentially hexadentante [O(-),N,E:E,N,O(-)] chalcogenated bisimine ligands L1-L3 have been synthesized by reaction of 1,1'-(4,6-dihydroxy-1,3-phenylene)bisethanone with H2N(CH2)2SPh, H2N(CH2)2SePh and H2N(CH2)2TeC6H4-4-OMe respectively. The L1-L3 react with Na2PdCl4 resulting in their partial hydrolysis, which appears to be metal-promoted. Of the two [(CH3)CN(CH2)2EAr] fragments
Magdy Shebl et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 126, 232-241 (2014-03-13)
Two new hydrazone ligands, H2L(1) and H2L(2), were synthesized by the condensation of 4,6-diacetylresorcinol with 3-hydrazino-5,6-diphenyl-1,2,4-triazine and isatin monohydrazone, respectively. The structures of the ligands were elucidated by elemental analyses, IR, (1)H NMR, electronic and mass spectra. Reactions of the
Structure of 4, 6-diacetylresorcinol.
Kokila MK, et al.
Acta Crystallographica Section C, Crystal Structure Communications, 48(6), 1133-1134 (1992)
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