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
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) |
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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