1,1'-(4,6-Dihydroxy-1,3-phenylen)bisethan-1-on

4,6-Diacetylresorcinol

HCID 75097CAS 2161-85-5

Teilstruktursuche Ähnliche Strukturen suchen

Grundinformationen

Standard-SMILES: CC(=O)c1cc(C(C)=O)c(O)cc1O
InChIKey: GEYCQLIOGQPPFM-UHFFFAOYSA-N
Summenformel: C10H10O4
Durchschnittliche Molmasse: 194,18 g/mol
Monoisotopische Masse: 194,0579088

Überblick

structure in first source

Namen und Bezeichner

Bevorzugter Name: 4,6-Diacetylresorcinol
IUPAC: 1-(5-acetyl-2,4-dihydroxyphenyl)ethanone
Lokaler Name: 1,1'-(4,6-Dihydroxy-1,3-phenylen)bisethan-1-on
Englischer Name: 4,6-Diacetylresorcinol
Summenformel: C10H10O4
Molmasse: 194.18

Namen und Synonyme

4,6-Diacetylresorcinol2161-85-5Ethanone, 1,1'-(4,6-dihydroxy-1,3-phenylene)bis-1,1'-(4,6-Dihydroxy-1,3-phenylene)bisethan-1-oneDTXSID50175994N8PEC3MAX6RefChem:409062DTXCID4098485218-482-8resodiacetophenone1,1'-(4,6-Dihydroxy-1,3-phenylene)diethanone1-(5-acetyl-2,4-dihydroxyphenyl)ethanone

Weitere Namen anzeigen

AKOS 236-352,4-Diacetyl-1,5-benzenediol4,6-Diacetyl-1,3-dihydroxybenzene1,1'-(4,6-Dihydroxy-1,3-phenylene)5'-Acetyl-2',4'-dihydroxyacetophenone

1,1'-(4,6-Dihydroxy-1,3-phenylene)bisethanoneMFCD000176551,1'-(4,6-Dihydroxy-1,3-phenylene)-bis-ethanone1,3-diacetyl-4,6-dihydroxybenzene1-(5-acetyl-2,4-dihydroxyphenyl)ethan-1-oneSCHEMBL12589954,6-Diacetyl-1,3-benzenediolSY063326

Datenbank-Bezeichner

CAS: 2161-85-5
PubChem CID: 75097
DTXSID: DTXSID50175994
UNII: N8PEC3MAX6
EC Number: 218-482-8
Nikkaji: J13.650F

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,7
Polarare Oberfläche (TPSA): 74,6 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 4
Frei drehbare Bindungen: 2
Schwere Atome: 14
Formalladung: 0
Komplexität: 225

Physikochemische Eigenschaften

Schmelzpunkt: 178 · 178-180 °C(lit.)
Siedepunkt: 399.9 · 399.9±27.0 °C(Predicted)
Dichte: 1.3 · 1.300±0.06 g/cm3(Predicted)
storage temp.: Inert atmosphere,Room Temperature
pka: 7.87 · 7.87±0.23(Predicted)
Aggregatzustand: Crystalline Powder
Farbe: White to off-white
InChI: 1S/C10H10O4/c1-5(11)7-3-8(6(2)12)10(14)4-9(7)13/h3-4,13-14H,1-2H3
InChIKey: GEYCQLIOGQPPFM-UHFFFAOYSA-N
SMILES: CC(=O)c1cc(C(C)=O)c(O)cc1O
CAS Datenbank: 2161 · 2161-85-5(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Sicherheitsdaten

wgk: 3
hs_code: 29145090
risk_code: 20/21/22-36/37/38
hazard_code: Xn
safety_code: 26-36
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3

Chemie und Industrie

Anwendungen · 1 Eintrag

Verwenden1,1′-(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

Darstellung · 1 Eintrag

synthetischePreparation 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%).