トリス(2-メチルフェニル)ホスフィン
トリス(2-メチルフェニル)ホスフィン · トリス(o-トリル)ホスフィン · 1-[ビス(2-メチルフェニル)ホスフィノ]-2-メチルベンゼン · トリ(o-トリル)ホスフィン · トリ(2-メチルフェニル)ホスフィン · トリス-o-トリルホスフィン · トリ-o-トリルホスフィン · トリス(o-メチルフェニル)ホスフィン
識別子と物理属性
| CAS No. | 6163-58-2 |
|---|---|
| 分子式 | C21H21P |
| 平均分子量 | 304.4 g/mol |
| 単同位体質量 | 304.1380873 g/mol |
| SMILES | Cc1ccccc1P(c1ccccc1C)c1ccccc1C |
| InChIKey | COIOYMYWGDAQPM-UHFFFAOYSA-N |
| PubChem CID | 80271 |
| EC No. | 228-193-9 |
| DTXSID | DTXSID9064130 |
| 現地名 | トリス(2-メチルフェニル)ホスフィン |
化学・物理的性質
| XLogP | 5.7 |
|---|---|
| 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 | 3 |
| 重原子数 | 22 |
| 形式電荷 | 0 |
| 複雑度 | 286 |
| 物質分類 | Other Classes -> Phosphorus Compounds |
| SpringerMaterials Properties | Crystal structure |
| Physical Description | Beige crystalline solid[Sigma-Aldrich MSDS] |
| 融点 | 123-125 °C(lit.) |
| 沸点 | 412.4±44.0 °C(Predicted) |
| 密度 | 1.16[at 20℃] |
| 蒸気圧 | 0Pa at 20℃ |
| 引火点 | 198°C (388°F) |
| 貯蔵条件 | Store below +30°C. |
| 溶解度 | クロロホルム、酢酸エチルアルコールに可溶。冷水にやや溶ける。水に不溶。 |
| 外観・状態 | 結晶性粉末 |
| 色 | 白い |
| BRN | 661212 |
| InChI | 1S/C21H21P/c1-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3/h4-15H,1-3H3 |
| InChIKey | COIOYMYWGDAQPM-UHFFFAOYSA-N |
| SMILES | Cc1ccccc1P(c2ccccc2C)c3ccccc3C |
| LogP（分配係数） | 7.2 |
| CAS データベース | 6163-58-2(CAS DataBase Reference) |
| NISTの化学物質情報 | Phosphine, tris(2-methylphenyl)-(6163-58-2) |
| EPAの化学物質情報 | Phosphine, tris(2-methylphenyl)- (6163-58-2) |
化学的特性
white to light yellow crystal powder.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 0.9% (1 of 113) of reports.WarningH315 (89.4%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 113 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Status: Active Update: 10-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24651Tri(o-tolyl)-phosphine: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | A skin and strong eye irritant[Sigma-Aldrich MSDS] See Triphenylphosphine. |
| Hazard Classes and Categories | Skin Irrit. 2 (89.4%) |
| F | 10-23 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 税関コード | 29319090 |
| 危険文句（R） | 36/37/38 |
| 化審法 | (3)-4357 |
| 危険表示 | Xi |
| 安全措置（S） | 26-36-37/39 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
用途
有機合成原料。
使用
Tri(o-tolyl)phosphine is used in a ruthenium-catalyzed direct amination of alcohols. It is also used in Suzuki reaction. Further, it is used in the preparation of tri-ortho-phosphinselenide by reacting with selenium as a reagent. In addition to this, it acts as a ligand in coordination chemistry.
製法・合成法
製造方法
Tri(o-tolyl)phosphine can be obtained by the reduction of tris(o-tolyl)phosphine oxide or prepared by the 2-bromotoluene Grignard reaction.Procedure: To a solution of magnesuim turnings (3.11 g, 128 mmol, 3.5 equiv) in THF (50 mL) was added a small amount of 2-bromotoluene (1 mL) and 1 iodine crystal. The reaction vessel was heated until initiation occurred, where upon a solution of the remaining 2-bromotoluene (20 g, 117 mmol, 3.2 equiv in total) in THF (100 mL) was added. The reaction was set to reflux for 2 hours (colour change to black solution), after which it was cooled to 0 oC and a solution of phosphorus trichloride (5.01 g, 36.5 mmol, 1 equiv) in THF (30 mL) was added dropwise. Upon addition completion the reaction was set to reflux for 18 hours. The reaction was allowed to cool to room temperature, whereupon NH4Cl solution was added with care. The resulting solution was extracted with ether (3 x 100 mL), dried over MgSO4, filtered and concentrated in vacuo. The resulting white solid was recrystalised from ethanol to yield Tri(o-tolyl)phosphine as a white solid. (6.8 g, 62 %)
純化方法
It crystallises from EtOH [Boert et al. J Am Chem Soc 109 7781 1987]. [Beilstein 16 III 835.]