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391794

Sigma-Aldrich

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

99%

Sinónimos:

4,6-Diacetylresorcinol

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About This Item

Fórmula lineal:
(HO)2C6H2(COCH3)2
Número de CAS:
2161-85-5
Peso molecular:
194.18
EC Number:
218-482-8
MDL number:
MFCD00017655
UNSPSC Code:
12352100
PubChem Substance ID:
24864402
NACRES:
NA.22

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

signalword

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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M Shebl et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 75(1), 428-436 (2009-12-08)
Mono- and binuclear VO(IV), Ce(III), Th(IV) and UO(2)(VI) complexes of thiosemicarbazone, semicarbazone and thiocarbohydrazone ligands derived from 4,6-diacetylresorcinol were synthesized. The structures of these complexes were elucidated by elemental analyses, IR, UV-vis, ESR, (1)H NMR and mass spectra as well
Cahit Demetgül
Carbohydrate polymers, 89(2), 354-361 (2012-06-20)
In this study, a new chitosan derivative (ketimine) was synthesized by condensation of chitosan with 4,6-diacetylresorcinol (DAR) at heterogeneous medium. The ketimine derivative of chitosan (DAR-chitosan) was characterized by elemental (C, H, N), spectral (DR-UV-vis and FT-IR spectroscopy), structural (powder
Magdy Shebl et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 113, 356-366 (2013-06-08)
Reactions of 4,6-diacetylresorcinol with different cobalt(II) and copper(II) salts viz., OAc(-), Cl(-), NO3(-) and SO4(2-), yielded a new series of binuclear metal complexes. Reactions of the ligand with these metal ions in the presence of a secondary ligand (L') [O,O-donor;
Design, Synthesis and Characterization of Bimetallic Palladium Complexes for Terminal Olefin Epoxidation
Netalkar SP, et al.
Catalysis Letters, 144(9), 1573-1583 (2014)
Mohammed Sardaryar Khan et al.
Acta poloniae pharmaceutica, 67(3), 261-266 (2010-06-09)
In the present study, a series of Mannich bases was synthesized by condensing 4,6-diacetylresorcinol with formaldehyde and some selected secondary amines following the Mannich reaction conditions. Findings revealed that Mannich reaction did not take place at the acetyl function but
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