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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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R 1 218,14

R 1 218,14

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5 G
R 1 218,14

About This Item

Linear Formula:
(HO)2C6H2(COCH3)2
CAS Number:
Molecular Weight:
194.18
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

R 1 218,14

List PriceR 1 243,00

Please contact Customer Service for Availability

Request a Bulk Order

Quality Level

Assay

99%

mp

178-180 °C (lit.)

functional group

ketone

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.[1] Its synthesis by acetylating resorcinol in the presence of zinc chloride has been reported.[2] The crystal structure of DAR has been studied.[3]

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[4][1][5][6]
  • hexadentate chalcogenated bisimine ligands[7]
  • 1,5-benzodiazepines[8]
  • ketimine of chitosan[9]
  • mannich bases[10]
  • hydrazone ligands[11]
  • thiosemicarbazone, semicarbazone and thiocarbohydrazone ligands[12]
  • binuclear cobalt(II) and copper(II) complexes[13]
  • europium (III) complexes[14]

Pictograms

Exclamation mark

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

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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
Structure of 4, 6-diacetylresorcinol.
Kokila MK, et al.
Acta Crystallographica Section C, Crystal Structure Communications, 48(6), 1133-1134 (1992)
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

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