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HomeProduct name list4,6-DIACETYLRESORCINOL

4,6-DIACETYLRESORCINOL

Synonym(s):4,6-Diacetylresorcinol

  • CAS NO.:2161-85-5
  • Empirical Formula: C10H10O4
  • Molecular Weight: 194.18
  • MDL number: MFCD00017655
  • EINECS: 218-482-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-06-08 17:06:37
4,6-DIACETYLRESORCINOL Structural

What is 4,6-DIACETYLRESORCINOL?

Chemical properties

Off-white powder

The Uses of 4,6-DIACETYLRESORCINOL

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

Preparation

Preparation by Friedel–Crafts acylation of resorcinol,
? with acetic anhydride,
– in the presence of zinc chloride
at 142–150° for 15 min (96%) or at 150–160° for 20 min (68%)
; – in the presence of ferric chloride
. – in the presence of concentrated sulfuric acid at 130° for 15 min (15%)
; – in the presence of 70% perchloric acid at 125–135° for 15–20 min (42%)
. ? with acetyl chloride,
– in the presence of zinc chloride, at 120°
; – in the presence of ferric chloride, at 150° for 15 min (60%) or at reflux for 30 min
; – in the presence of concentrated sulfuric acid (18%)
. ? by a typical Friedel–Crafts reaction (24%).

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.

Properties of 4,6-DIACETYLRESORCINOL

Melting point: 178-180 °C(lit.)
Boiling point: 399.9±27.0 °C(Predicted)
Density  1.300±0.06 g/cm3(Predicted)
storage temp.  Inert atmosphere,Room Temperature
form  Crystalline Powder
pka 7.87±0.23(Predicted)
color  White to off-white
λmax 370nm(DMF)(lit.)
CAS DataBase Reference 2161-85-5(CAS DataBase Reference)

Safety information for 4,6-DIACETYLRESORCINOL

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 4,6-DIACETYLRESORCINOL

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