アセチルフェロセン
アセチルフェロセン · アセチルフェロセン, 99.5% · 1-ACETYLFERROCENE · Acetylferrocene,95% · Monoacetylferrocene · Acetoferrocene · Acetyferrocene · 25gx1
識別子と物理属性
| CAS No. | 1271-55-2 |
|---|---|
| 分子式 | C12H12FeO10* |
| 平均分子量 | 228.07 g/mol |
| SMILES | CC(=O)[c-]1[c-][c-][c-][c-]1.[Fe+2].[c-]1[c-][c-][cH-][c-]1 |
| PubChem CID | 24190835 |
| 現地名 | アセチルフェロセン |
化学・物理的性質
| 融点 | 81-83 °C (lit.) |
|---|---|
| 沸点 | 160-163 °C (3.0004 mmHg) |
| 密度 | >1 g/cm3 (20℃) |
| 引火点 | 160-163°C/4mm |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 外観・状態 | 針状結晶性粉末 |
| 色 | オレンジ |
| 溶解度 | 不溶性 |
| 安定性 | 安定。強酸化剤、還元剤、強酸、強塩基とは相容れない。 |
| InChI | InChI=1S/C7H7O.C5H5.Fe/c1-6(8)7-4-2-3-5-71-2-4-5-3-1/h2-5H,1H31-5H |
| InChIKey | PHMAOJNZIFULOG-UHFFFAOYSA-N |
| SMILES | [C]1(C(=O)C)[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1.[Fe] |^1:0,4,5,6,7,8,9,10,11,12| |
| CAS データベース | 1271-55-2(CAS DataBase Reference) |
| NISTの化学物質情報 | Acetylferrocene(1271-55-2) |
| EPAの化学物質情報 | Ferrocene, acetyl- (1271-55-2) |
化学的特性
orange crystalline powder
安全性と法規制
| F | 10 |
|---|---|
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | OB3700000 |
| 輸送番号（UN） | UN 2811 6.1/PG 2 |
| 毒性 | LDLo orl-rat: 5 mg/kg EPASR* 8EHQ-1285-0578 |
| 税関コード | 29310095 |
| 危険文句（R） | 28 |
| 危険表示 | T+ |
| 安全措置（S） | 28-36/37-45-28A-1 |
| 危険等級 | 6.1Acute Tox. 1 DermalAcute Tox. 2 Oral |
| 包装等級 | II |
| 貯蔵分類 | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| 危険度評価（NFPA 704基準/消防庁データ） | 人的[青]=3 |
用途
用途
有機合成原料。
使用
1-Acetylferrocene was originally used in military or space field as an additive in rocket propellant, to promote the burning rate. Its ferrocenyl derivative has wide applications to biological and medical fields such as ferrocene-modified beta-lactam because of its physiological activity of anti-malarial, anti-tumor, bactericidal, anti-inflammatory, treatment of anemia, inhibition of enzymatic activity and so on by virtue of its unique structure and diverse properties.
製法・合成法
製造方法
Acetylferrocene synthesis: Charge a 25 mL round bottom flask with ferrocene (1 g) and acetic anhydride (3.3 mL). Carefully add phosphoric acid (0.7 mL, 85%) and heat the reaction mixture on a hot water bath for 20 min with stirring. Pour the hot mixture onto crushed ice (27 g). After all the ice has melted, neutralise the solution with solid sodium bicarbonate and cool for a further 5 min. Collect the brown precipitate by filtration, wash with water and dry in the air. The solid obtained is a mixture of unreacted ferrocene and the monosubstituted product acetylferrocene (Figure 1). However, a third compound may also be present in very small amounts as the disubstituted product of acetylation (1,1′-diacetylferrocene).
純化方法
Orange-red crystals are obtained when it is recrystallised from isooctane or *C6H6, and then sublimed at 100o/1mm. The oxime has m 167-170o (from Et2O or aqueous EtOH). The semicarbazone has m 198-201o (from EtOH). [Richmond & Freiser J Am Chem Soc 77 2022 1955, Weinmayer J Am Chem Soc 77 3009 1955, Broadhead et al. J Chem Soc 650 1958, Beilstein 16 IV 1798.]