CAS 2161-85-5 4,6-Diacetylresorcinol (HCID 75097)

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Basic information

CAS: 2161-85-5
Standard SMILES: CC(=O)c1cc(C(C)=O)c(O)cc1O
InChIKey: GEYCQLIOGQPPFM-UHFFFAOYSA-N
Molecular formula: C10H10O4
Average molar mass: 194.18 g/mol
Monoisotopic mass: 194.0579088

Overview

structure in first source

Names & identifiers

Preferred name: 4,6-Diacetylresorcinol
IUPAC: 1-(5-acetyl-2,4-dihydroxyphenyl)ethanone
English name: 4,6-Diacetylresorcinol
Molecular formula: C10H10O4
Molecular weight: 194.18

Names & synonyms

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

Show more names

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

Database identifiers

CAS: 2161-85-5
PubChem CID: 75097
DTXSID: DTXSID50175994

Properties

Computed structural properties

XLogP: 1.7
Topological polar surface area: 74.6 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 14
Formal charge: 0
Complexity: 225

Physicochemical properties

Melting point: 178 · 178-180 °C(lit.)
Boiling point: 399.9 · 399.9±27.0 °C(Predicted)
Density: 1.3 · 1.300±0.06 g/cm3(Predicted)
storage temp.: Inert atmosphere,Room Temperature
pka: 7.87 · 7.87±0.23(Predicted)
form: Crystalline Powder
color: White to off-white
λmax: 370 nm · 370nm(DMF)(lit.)
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 DataBase Reference: 2161 · 2161-85-5(CAS DataBase Reference)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 29145090
risk_code: 20/21/22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H302+H312+H332-H315-H319-H335
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338

Chemistry & industry

Applications · 2 items

Uses1,1′-(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

General Description1,1′-(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.

Preparation methods · 1 item

PreparationPreparation 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%).