Maximum quantity allowed is 999
请选择数量
CAS RN: 603-35-0 | 产品编码: T0519
Triphenylphosphine
×
![]()
×
技术规格
| Appearance | White powder to lump |
| Purity(Iodometric Titration) | min. 95.0 % |
| Melting point | 80.0 to 82.0 °C |
| Solubility in Toluene | very faint turbidity |
| NMR | confirm to structure |
物性（参考值）
| 熔点 | 81 °C |
| 沸点 | 260 °C/25 mmHg |
| 水溶性 | 不溶 |
| 在水中的溶解度 | 0.3 mg/l 25 °C |
| 溶解性（可溶于） | 苯, 甲苯, 氯仿 |
| 溶解性（微溶于） | 醇 |
GHS
| 象形图 |
|
| 信号词 | Danger |
| 危险性说明 | H302 : Harmful if swallowed. H315 : Causes skin irritation. H319 : Causes serious eye irritation. H372 : Causes damage to organs through prolonged or repeated exposure. H373 : May cause damage to organs through prolonged or repeated exposure. H317 : May cause an allergic skin reaction. H335 : May cause respiratory irritation. H413 : May cause long lasting harmful effects to aquatic life. |
| 防范说明 | P501 : Dispose of contents/ container to an approved waste disposal plant. P273 : Avoid release to the environment. P272 : Contaminated work clothing should not be allowed out of the workplace. P260 : Do not breathe dust/ fume/ gas/ mist/ vapors/ spray. P270 : Do not eat, drink or smoke when using this product. P271 : Use only outdoors or in a well-ventilated area. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ eye protection/ face protection. P302 + P352 : IF ON SKIN: Wash with plenty of water. P314 : Get medical advice/ attention if you feel unwell. P337 + P313 : If eye irritation persists: Get medical advice/ attention. P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P362 + P364 : Take off contaminated clothing and wash it before reuse. P333 + P313 : If skin irritation or rash occurs: Get medical advice/ attention. P301 + P312 + P330 : IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Rinse mouth. P304 + P340 + P312 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Call a POISON CENTER/doctor if you feel unwell. P403 + P233 : Store in a well-ventilated place. Keep container tightly closed. P405 : Store locked up. |
相关法规
| RTECS# | SZ3500000 |
运输信息
| HS编码* | 2931.49-900 |
应用
t-Butyldimethylsilylation of Alcohols using TBS Reagents
References
- 1)A New Method for Silylation of Hydroxylic Compounds: Reaction of Phenols and Alcohols with Silanols Mediated by Diethyl Azodicarboxylate and Triphenylphosphine
- 2)Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols
- P. G. M. Wuts, in Greene’s Protective Groups in Organic Synthesis, 5th ed., ed. by P. G. M. Wuts, John Wiley & Sons, Inc., Hoboken, New Jersey, 2014, Chap. 2, 17.
应用
Protection and deprotection of PMP groups
Reference
- Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols
- P. G. M. Wuts, in Greene’s Protective Groups in Organic Synthesis, 5th ed., ed. by P. G. M. Wuts, John Wiley & Sons, Inc., Hoboken, New Jersey, 2014, Chap. 2, 17.
应用
Corey-Fuchs Alkyne Synthesis
Typical Procedure:
Carbon tetrabromide (34.67 g, 104.5 mmol) and anhydrous CH2Cl2 (175 mL) are added to a 500 mL round bottom flask equipped with a magnetic stir bar and septum under N2 atmosphere. The reaction flask is cooled to 0 ℃ with an ice bath for 10 min. Triphenylphosphine (54.84 g, 209.1 mmol) is added in portions over 5 min, and the dark red solution is stirred at 0 ℃ for 30 min. 3,4-Dimethoxybenzaldehyde (17.37 g, 104.5 mmol) is added and the mixture is stirred at 0 ℃ for 1 h. A 1 : 1 mixture of H2O : brine is added and the layers are separated. The aqueous layer is extracted with a 1 : 1 mixture of hexanes : CH2Cl2, and the combined organic layers are dried, filtered, and concentrated under reduced pressure. The crude material is chromatographed on SiO2 (0-15% EtOAc/hexanes) to afford the dibromide 1 (29.37 g, Y. 88%) as a yellow oil.
Then, 1 (4.41 g, 13.79 mmol, 1.0 equiv) and THF (45 mL) are added to a 250 mL round bottom flask equipped with a magnetic stir bar and septum, and the reaction flask is cooled to -78 ℃ under N2 atmosphere. 2.5M n-BuLi solution in hexane (11.6 mL) is added slowly via syringe and the reaction solution is stirred at -78 ℃ for 45 min and then at 0 ℃ for 45 min. The flask is recooled to -78 ℃, and freshly distilled methyl chloroformate (1.1 mL, 1.3 mmol, 1.0 equiv) is added slowly via syringe. The mixture is stirred at -78 ℃ for 10 min, then 0 ℃ for 1 h. Saturated aqueous NH4Cl solution is added, and the layers are separated. The aqueous layer is extracted with Et2O, and the combined organic layers are dried, filtered and concentrated under reduced pressure. The residue is chromatographed (SiO2, 2-20% EtOAc / hexanes) to afford the desired alkyne 2 (2.83 g, Y. 93%) as a white solid.
Carbon tetrabromide (34.67 g, 104.5 mmol) and anhydrous CH2Cl2 (175 mL) are added to a 500 mL round bottom flask equipped with a magnetic stir bar and septum under N2 atmosphere. The reaction flask is cooled to 0 ℃ with an ice bath for 10 min. Triphenylphosphine (54.84 g, 209.1 mmol) is added in portions over 5 min, and the dark red solution is stirred at 0 ℃ for 30 min. 3,4-Dimethoxybenzaldehyde (17.37 g, 104.5 mmol) is added and the mixture is stirred at 0 ℃ for 1 h. A 1 : 1 mixture of H2O : brine is added and the layers are separated. The aqueous layer is extracted with a 1 : 1 mixture of hexanes : CH2Cl2, and the combined organic layers are dried, filtered, and concentrated under reduced pressure. The crude material is chromatographed on SiO2 (0-15% EtOAc/hexanes) to afford the dibromide 1 (29.37 g, Y. 88%) as a yellow oil.
Then, 1 (4.41 g, 13.79 mmol, 1.0 equiv) and THF (45 mL) are added to a 250 mL round bottom flask equipped with a magnetic stir bar and septum, and the reaction flask is cooled to -78 ℃ under N2 atmosphere. 2.5M n-BuLi solution in hexane (11.6 mL) is added slowly via syringe and the reaction solution is stirred at -78 ℃ for 45 min and then at 0 ℃ for 45 min. The flask is recooled to -78 ℃, and freshly distilled methyl chloroformate (1.1 mL, 1.3 mmol, 1.0 equiv) is added slowly via syringe. The mixture is stirred at -78 ℃ for 10 min, then 0 ℃ for 1 h. Saturated aqueous NH4Cl solution is added, and the layers are separated. The aqueous layer is extracted with Et2O, and the combined organic layers are dried, filtered and concentrated under reduced pressure. The residue is chromatographed (SiO2, 2-20% EtOAc / hexanes) to afford the desired alkyne 2 (2.83 g, Y. 93%) as a white solid.
References
- Total synthesis of (+)-Lithospermic acid by asymmetric intramolecular alkylation via catalytic C-H bond activation
应用
Corey-Nicolaou Macrolactonization1)
Typical Procedure:
To a stirred solution of the hydroxy carboxylic acid 1 (125 mg, 0.422 mmol) in dry CH2Cl2 (15 mL) is added triphenylphosphine (125 mg, 0.48 mmol) followed by 2,2’-dipyridyl disulfide (105 mg, 0.48 mmol) and the mixture is stirred until TLC (ethyl acetate : hexane = 2 : 3) shows complete loss of starting material (usually 0.5 h – 2 h). The mixture is concentrated in vacuo and dissolved in dry toluene (150 mL). To the solution is added 0.006M AgBF4 solution in toluene (1.2 mL) and the mixture is heated under reflux for 12 h. The mixture is cooled and solvents removed in vacuo. The residue is purified by flash column chromatography (acetone : CH2Cl2 = 0.5 : 99.5) to afford the desired lactone 2 (95 mg, Y. 81%).
To a stirred solution of the hydroxy carboxylic acid 1 (125 mg, 0.422 mmol) in dry CH2Cl2 (15 mL) is added triphenylphosphine (125 mg, 0.48 mmol) followed by 2,2’-dipyridyl disulfide (105 mg, 0.48 mmol) and the mixture is stirred until TLC (ethyl acetate : hexane = 2 : 3) shows complete loss of starting material (usually 0.5 h – 2 h). The mixture is concentrated in vacuo and dissolved in dry toluene (150 mL). To the solution is added 0.006M AgBF4 solution in toluene (1.2 mL) and the mixture is heated under reflux for 12 h. The mixture is cooled and solvents removed in vacuo. The residue is purified by flash column chromatography (acetone : CH2Cl2 = 0.5 : 99.5) to afford the desired lactone 2 (95 mg, Y. 81%).
References
- 1)Efficient and mild lactonization method for the synthesis of macrolides
- 2)Facile synthesis of saturated eight-membered ring lactones
参考文献
文章/手册
TCIMail
[TCIMAIL No.156] Mitsunobu Reaction Using Acetone Cyanohydrin[产品拾贝] 含有吡啶硫脲结构的手性衍生化试剂
[TCI应用实例] 通过Appel反应进行烷基醇的溴化
产品文档 (部分产品的分析图谱无法提供，敬请谅解。)
化学品安全说明书(SDS)
请选择语言。
如需更多帮助，请联系我 们。
技术规格
CoA及其他文档
请输入批号
批号输入有误。请输入中横线前的4-5个字母数字字符。
示例 CoA
可下载CoA示例。注：该示例不一定是最新批次的CoA。
目前没有该产品的 CoA 示例。
分析图谱
请输入批号
批号输入有误。请输入中横线前的4-5个字母数字字符。
很抱歉，您搜索的分析图谱无法提供。