1,1'-(4,6-ジヒドロキシ-1,3-フェニレン)ビスエタノン

4,6-Diacetylresorcinol

HCID 75097

ノート反応

部分構造検索類似構造を探す

基本情報

CAS: 2161-85-5
標準SMILES: CC(=O)c1cc(C(C)=O)c(O)cc1O
InChIKey: GEYCQLIOGQPPFM-UHFFFAOYSA-N
分子式: C10H10O4
平均分子量: 194.18 g/mol
単同位体質量: 194.0579088

概要

structure in first source

名称と識別子

優先名称: 4,6-Diacetylresorcinol
IUPAC: 1-(5-acetyl-2,4-dihydroxyphenyl)ethanone
現地名: 1,1'-(4,6-ジヒドロキシ-1,3-フェニレン)ビスエタノン
英語名: 4,6-Diacetylresorcinol
分子式: C10H10O4
分子量: 194.18

名称と別名

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

名称をさらに表示

5'-アセチル-2',4'-ジヒドロキシアセトフェノン2,4-ジアセチル-1,5-ベンゼンジオールレソジアセトフェノン1,1'-(4,6-ジヒドロキシ-1,3-フェニレン)ビスエタノン4,6-ジアセチルレソルシノール4,6-ジアセチル-1,3-ジヒドロキシベンゼン1,1′‐(4,6‐ジヒドロキシ‐1,3‐フェニレン)ビスエタノン4,6-ジアセチルレゾルシノール1,1′-(4,6-ジヒドロキシ-1,3-フェニレン)ビスエタノン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

データベース識別子

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

物性

構造計算による物性

XLogP: 1.7
極性表面積: 74.6 Å²
水素結合供与体数: 2
水素結合受容体数: 4
回転可能結合数: 2
重原子数: 14
形式電荷: 0
複雑度: 225

物理化学的性質

融点: 178 · 178-180 °C(lit.)
沸点: 399.9 · 399.9±27.0 °C(Predicted)
比重(密度): 1.3 · 1.300±0.06 g/cm3(Predicted)
貯蔵温度: Inert atmosphere,Room Temperature
酸解離定数(Pka): 7.87 · 7.87±0.23(Predicted)
外見: 結晶性粉末
色: ホワイトからオフホワイト
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 データベース: 2161 · 2161-85-5(CAS DataBase Reference)

化学的性質

化学的特性Off-white powder

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (100%)

安全データ

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

化学と産業

応用分野 · 3 件

用途有機合成原料。

使用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

一般的な説明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.

調製方法 · 1 件

製造方法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%).