9-メチレン-9H-フルオレン
ジベンゾフルベン · 9-メチレン-9H-フルオレン · 9-メチリデン-9H-フルオレン · Dibenzofulvene · 9-methylidenefluorene · Fluorenylidenemethane · 9-methylenefluorene · 9-Methylene-9H-fluorene
識別子と物理属性
| CAS No. | 4425-82-5 |
|---|---|
| 分子式 | C14H10 |
| 平均分子量 | 178.23 g/mol |
| 単同位体質量 | 178.07825032 g/mol |
| SMILES | C=C1c2ccccc2-c2ccccc21 |
| InChIKey | ZYASLTYCYTYKFC-UHFFFAOYSA-N |
| PubChem CID | 78147 |
| EC No. | 817-307-8 |
| DTXSID | DTXSID90196082 |
| 現地名 | 9-メチレン-9H-フルオレン |
化学・物理的性質
| XLogP | 3.7 |
|---|---|
| 極性表面積 | 0 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 0 |
| 回転可能結合数 | 0 |
| 重原子数 | 14 |
| 形式電荷 | 0 |
| 複雑度 | 216 |
| Kovats Retention Index | 292.4292.28279.3291.8 |
| 融点 | 46-48 °C |
| 沸点 | 305.9±12.0 °C(Predicted) |
| 密度 | 1.12±0.1 g/cm3(Predicted) |
| 貯蔵条件 | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| 溶解度 | クロロホルム（微量）、酢酸エチル（微量） |
| 外観・状態 | 個体 |
| 色 | オフホワイトからペールベージュ |
| 安定性 | 光に敏感 |
| InChI | InChI=1S/C14H10/c1-10-11-6-2-4-8-13(11)14-9-5-3-7-12(10)14/h2-9H,1H2 |
| InChIKey | ZYASLTYCYTYKFC-UHFFFAOYSA-N |
| SMILES | C1(=C)C2=C(C=CC=C2)C2=C1C=CC=C2 |
化学的特性
9-methylidenefluorene or dibenzofulvene (DBF) is a polycyclic aromatic hydrocarbon with chemical formula C14H10.9-methylidenefluorene is an intermediate of Fmoc cleavage reaction. It is an analog of a 1,1-diphenylethylene. Polymerization of 9-methylene-fluorene produces a π-stacked polymer.
安全性と法規制
| GHS 分類 | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%)Eye Irrit. 2A (100%)STOT SE 3 (100%) |
| 注意喚起語 | 警告 |
| 危険有害性情報 | コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H302 |
用途
説明
9-Methylene-9H-fluorene is a fluorescent probe that can be used to detect the presence of hydroxyl groups in vitro. It reacts with the hydroxyl group on the substrate film and emits light, which is then detected using a fluorometer. The reaction mechanism is shown below. Fluorophores are often used for sample preparation because they are relatively stable and can be easily removed from the final product. 9-Methylene-9H-fluorene has been shown to enhance cationic polymerization, which can lead to improved efficacy in some applications.
使用
9-Methylidenefluorene is an analog of 9-Methylfluorene (M305335); a compound that has been shown to be mutagenic in Salmonella typhimurium TA98 and TA100 in the presence of 9000 X g supernantant from Aroclor-induced rats.
製法・合成法
製造方法
A suspension of methyl triphenylphosphonium bromide (31.22 g; 87.3 mmol) in 500 mL of ether was added at -30°C. 10M n-butyllithium in hexane (8.73 mL; 87.3 mmol) was added to the mixture, and the mixture was stirred at room temperature for 1-2 hours. To the above mixture, 15 g (83.2 mmol) of 9-fluorenone in 50 mL of tetrahydrofuran was added, and the mixture was refluxed for 1 hour. After cooling the above mixture to 0°C, 9-Methylene-9H-fluorene was obtained after purification.