2161-85-5

Basic information

• Product Name: 4,6-DIACETYLRESORCINOL
• Synonyms: Ethanone, 1,1'-(4,6-dihydroxy-1,3-phenylene)bis-;4,6-DIACETYLRESORCINOL;AKOS 236-35;1,1'-(4,6-DIHYDROXY-1,3-PHENYLENE)BISETHANONE;1-(5-ACETYL-2,4-DIHYDROXYPHENYL)ETHAN-1-ONE;RESODIACETOPHENONE;1,1'-(4,6-dihydroxy-1,3-phenylene)bisethan-1-one;2,4-Diacetyl-1,5-benzenediol
• CAS NO: 2161-85-5
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• EINECS: 218-482-8
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Building Blocks;C10;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 2161-85-5.mol
• Article Data: 39

Chemical Properties

• Melting Point: 178-180 °C(lit.)
• Boiling Point: 399.9 °C at 760 mmHg
• Flash Point: 209.8 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.3g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.87±0.23(Predicted)
• CAS DataBase Reference: 4,6-DIACETYLRESORCINOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-DIACETYLRESORCINOL(2161-85-5)
• EPA Substance Registry System: 4,6-DIACETYLRESORCINOL(2161-85-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2161-85-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-white powder

Uses

1,1′-(4,6-Dihydroxy-1,3-phenylene)bisethanone (4,6-diacetylresorcinol, DAR) may be used in the synthesis of the following:Schiff base ligandshexadentate chalcogenated bisimine ligands1,5-benzodiazepinesketimine of chitosanmannich baseshydrazone ligandsthiosemicarbazone, semicarbazone and thiocarbohydrazone ligandsbinuclear 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.

Upstream product

• 108-24-7 acetic anhydride 
• 108-46-3 recorcinol 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 64-19-7 acetic acid 
• 2049-73-2 2,4-diethoxybenzene 
• 75-36-5 acetyl chloride 
• 108-58-7 Resorcinol diacetate 
• 3098-67-7 1,1'-(4,6-dimethoxy-1,3-phenylene)diethanone 
• 39251-52-0 5-acetyl-2,4-bis(3-methylbut-2-enyloxy)acetophenone 
• 7446-70-0 aluminium trichloride 
• 151-10-0 1,3-Dimethoxybenzene 
• 10025-87-3 trichlorophosphate 
• 7664-93-9 sulfuric acid 
• 42059-48-3 acetic acid 4-acetyl-3-hydroxyphenyl ester 

Downstream Products

• 52597-56-5 3,7-dibenzoyl-2,8-diphenyl-pyrano[3,2-g]chromene-4,6-dione 
• 115540-52-8 4,6-di(2-thienylcinnamoyl)resorcinol 
• 117690-94-5 4-(4-cyanobutoxy)-5-acetyl-2-hydroxy-acetophenone 
• 145489-92-5 2-hydroxy-3-iodo-4-phenoxy-5-acetyl-acetophenone 
• 137369-23-4 (E)-1-[2,4-Dihydroxy-5-((E)-3-p-tolyl-acryloyl)-phenyl]-3-p-tolyl-propenone 
• 124469-44-9 (E)-3-(2-Chloro-phenyl)-1-{5-[(E)-3-(2-chloro-phenyl)-acryloyl]-2,4-dihydroxy-phenyl}-propenone 
• 115540-48-2 4,6-di(o-chlorocinnamoyl)resorcinol 
• 32140-71-9 2',4'-dihydroxy-5'-(4-methoxy)cinnamoyl-4-methoxychalcone 
• 137369-22-3 (2E,2'E)-1,1'-[4,6-dihydroxy-1,3-phenylene]bis(3-(4-methoxyphenyl)prop-2-en-1-one) 
• 52597-53-2 1,1'-(4,6-dihydroxybenzene-1,3-diyl)bis(3-phenylpropane-1,3-dione) 
• 134248-21-8 (E)-3-(2,4-Dichloro-phenyl)-1-{5-[(E)-3-(2,4-dichloro-phenyl)-acryloyl]-2,4-dihydroxy-phenyl}-propenone 
• 405260-16-4 1-[2,4-Dihydroxy-5-(3-oxo-butyryl)-phenyl]-butane-1,3-dione 
• 114649-83-1 1-[2,4-Dihydroxy-5-(3-oxo-hexanoyl)-phenyl]-hexane-1,3-dione 
• 115540-49-3 4,6-di(m-chlorocinnamoyl)resorcinol 

Relevant articles and documents

Conductance studies on complex formation of nano Cu(NO3)2.2.5H2O with 4,6-diacetylresorcinol in mixed solvents

The different complexation thermodynamic parameters for example, formation constants (Kf), free energies of formation (?Gf), enthalpies of formation (?Hf) and entropies of formation (?Sf) for nano copper nitrate hemi pentahydrate (Cu(NO3)2.2.5H2O) with 4,6-diacetylresorcinol as a ligand in pure DMF and in mixed solvents of DMF and water are calculated at different temperatures, 293.15, 303.15, 313.15 and 323.15 K by using conductance measurements. By drawing the relation between molar conductance and ratio of metal to ligand, the figures indicate the formation of two types of complexes with M:L ratios 1:2 and 1:1 stoichiometric complexes.

Spectroscopic and biological studies of mono- or binuclear complexes derived from thio-Schiff bases of some transition metals

Two novel Schiff base ligands, 4,6-bis((E)-1-(2-mercaptophenylimino)ethyl) benzene-1,3-diol, H4La, and 1,2-((E)-1-(6-((E)-1-(2-mercaptophenylimino)ethyl) pyridine-2-yl)ethylideneamino)benzenthiol, H2Lb, have been synthesized by the condensation of 4,6-diacetyl resorcinol (DAR) or 2,6-diacetyl pyridine (DAP) with 2-aminobenzenthiol (ABT), in the molar ratio 1:2 [1 (DAR or DAP):2 ABT]. The structures of ligands were elucidated by elemental analysis, infrared (IR), UV-VIS as well as 1H-NMR. Reaction of the Schiff base ligands with the transition metals Co(II), Ni(II), Cu(II), Zn(II), VO(IV) and Ru(III) afforded two series of the corresponding transition metal complexes in the molar ratio 1:2 or 1:1. The ligand, H4La, behaves as tetrabasic hexadentate, which hosts the two metal ions at the centers of two SNO sites, while H2Lb acts as a compartmental dibasic pentadentate ligand forming mono- or binuclear complexes through the coordinate sites N3S2. The structures of the newly prepared complexes were characterized on the basis of the elemental analysis, spectroscopic data (IR, UV-VIS, 1H-NMR and ESR spectra along with magnetic susceptibility measurements) besides the molar conductance measurements and thermal gravimetric analyses. The bonding sites are the azomethane, sulfur atoms and phenolic oxygen for H4La or pyridine nitrogen for H2Lb. The complexes exhibit mono- or binuclear structures, distorted octahedral, tetrahedral, square planar or square pyramid structure. Synthesized compounds have also been screened for their biological activity against species of pathogenic fungi and bacteria and were found to possess appreciable fungicidal and bactericidal properties.

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Metal free Friedel-Crafts di-acetylation of resorcinol in acetic acid

Conventionally, the metal catalyst used for Friedel-Crafts acetylation is poisonous and the acetylating agent is not readily available. Herein, methane sulfonic acid is developed to perform Friedel-Crafts diacetylation of aromatics instead of metal catalyst. Furthermore, acetic acid is employed as acetylating agent to replace acetic anhydride. By this approach, 4,6-diacetylresorcinol, known as an indispensable intermediate in superior fiber polybenzoxazole synthesis, is prepared in high yield from resorcinol. The results obtained by 1H NMR, FT-IR and HPLC analysis indicate that methane sulfonic acid is an efficient catalyst for Friedel-Crafts acetylation and acetic anhydride can be avoid by replacement with acetic acid, in which phosphorus pentoxide is helpful to improve conversion of desired product.

4,6-Diacetylresorcinol in heterocyclic synthesis Part II: Synthesis of some novel 4,6-bis(azolyl/azinyl/ azepinyl)resorcinols

– A series of new 4,6-bis(azolyl/azinyl/azepinyl)resorcinols was synthesized in a combinatorial manner besides, (2E,2'E)-4,6-bis[3-(aminophenyl-substituted)prop-2-en-1-oxo-1-yl]resorcinols were also obtained. Heterocyclization of (2E,2'E)-4,6-bis[3-(dimethylamino)prop-2-en-1-oxo-1-yl]resorcinol (2) with nitrogen-containing binucleophiles afforded the target compounds. All the newly synthesized compounds were characterized by spectral tools.