트리-o-톨릴포스핀
트리-o-톨릴포스핀 · P(o-tol)3 · TRI-O-TOLYLPHOSPHINE · P(o-tolyl)3 · Tri-o-tolylphosphane · TRIS(2-METHYLPHENYL)PHOSPHINE · TRIS(O-TOLYL)PHOSPHINE · TRI-O-TOLYPHOSPHINE
식별자 및 물리적 특성
| CAS No. | 6163-58-2 |
|---|---|
| 분자식 | C21H21P |
| 평균 분자량 | 304.4 g/mol |
| 단동위원소 질량 | 304.1380873 g/mol |
| SMILES | Cc1ccccc1P(c1ccccc1C)c1ccccc1C |
| InChIKey | COIOYMYWGDAQPM-UHFFFAOYSA-N |
| PubChem CID | 80271 |
| EC No. | 228-193-9 |
| DTXSID | DTXSID9064130 |
| 현지명 | 트리-o-톨릴포스핀 |
화학 및 물리적 성질
| XLogP | 5.7 |
|---|---|
| 극성 표면적 | 0 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 0 |
| 회전 가능 결합 수 | 3 |
| 무거운 원자 수 | 22 |
| 형식 전하 | 0 |
| 복잡도 | 286 |
| 물질 분류 | Other Classes -> Phosphorus Compounds |
| SpringerMaterials Properties | Crystal structure |
| Physical Description | Beige crystalline solid[Sigma-Aldrich MSDS] |
| 녹는점 | 123-125 °C(lit.) |
| 끓는 점 | 412.4±44.0 °C(Predicted) |
| 밀도 | 1.16[at 20℃] |
| 증기압 | 0Pa at 20℃ |
| 인화점 | 198°C (388°F) |
| 저장 조건 | Store below +30°C. |
| 용해도 | 클로로포름, 에틸아세테이트에 용해됨 |
| 물리적 상태 | 결정성 분말 |
| 색상 | 하얀색 |
| 용해도 | 알코올에 용해됩니다. 찬물에 약간 용해됩니다. 물에 불용성. |
| 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(분배 계수) | 7.2 |
| NIST | Phosphine, tris(2-methylphenyl)-(6163-58-2) |
| EPA | Phosphine, tris(2-methylphenyl)- (6163-58-2) |
화학적 성질
white to light yellow crystal powder.
안전 및 규제
| GHS 분류 | 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. |
|---|---|
| 규제 정보 | 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 |
| 유해성 요약 | A skin and strong eye irritant[Sigma-Aldrich MSDS] See Triphenylphosphine. |
| Hazard Classes and Categories | Skin Irrit. 2 (89.4%) |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| 관세 코드 | 29319090 |
| 위험 문구(R) | 36/37/38 |
| 위험 표시 | Xi |
| 안전 문구(S) | 26-36-37/39 |
| F 고인화성물질 | 10-23 |
| 저장 분류 | 11 - Combustible Solids |
용도
용도
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.
제조 및 합성 방법
제조 방법
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 %)