|
ChemicalBook Optimization Suppliers |
| 名前: |
SHANG FLUORO Gold |
| 電話番号: |
021-021-65170832 15601903708 |
| 電子メール: |
qinba_1@163.com |
|
| | トリフルオロメタンスルホン酸トリイソプロピルシリル 製品概要 |
| | トリフルオロメタンスルホン酸トリイソプロピルシリル 物理性質 |
| 沸点 | 45-46 °C/0.03 mmHg | | 比重(密度) | 1.14 g/mL at 25 °C (lit.) | | 屈折率 | n20/D 1.415(lit.) | | 闪点 | 213 °F | | 貯蔵温度 | under inert gas (nitrogen or Argon) at 2-8°C | | 溶解性 | Miscible with chloroform and ethyl acetate. | | 外見 | Liquid | | 比重 | 1.14 | | 色 | Clear light brown to orange-brown | | Sensitive | Moisture Sensitive | | Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents | | BRN | 3591541 | | InChI | InChI=1S/C10H21F3O3SSi/c1-7(2)18(8(3)4,9(5)6)16-17(14,15)10(11,12)13/h7-9H,1-6H3 | | InChIKey | LHJCZOXMCGQVDQ-UHFFFAOYSA-N | | SMILES | C(F)(F)(F)S(O[Si](C(C)C)(C(C)C)C(C)C)(=O)=O | | CAS データベース | 80522-42-5(CAS DataBase Reference) |
| | トリフルオロメタンスルホン酸トリイソプロピルシリル Usage And Synthesis |
| 外観 | 無色～褐色、液体 | | 使用上の注意 | 不活性ガス封入 | | 化学的特性 | clear light brown to orange-brown liquid | | 物理的性質 | Colorless oil; bp 83–87 °C/1.7 mmHg; d 1.173
g cm?3. | | 使用 | Triisopropylsilyl trifluoromethanesulfonate is used as a reagent for the introduction of triisopropylsilyl(TIPS) group in organic synthesis. It is involved in the synthesis of 2-substituted benzothiopyran-4-ones and silyloxy acetylenes. As a protecting group in organic synthesis, it is utilized especially for the protection of primary amines. Furthermore, it plays an important role in Takahashi Taxol total synthesis or for chemical glycosylation reactions. | | 使用 | Triisopropylsilyl Trifluoromethanesulfonate is a highly reactive silylating agent and Lewis acid capable of converting
primary and secondary alcohols to the corresponding triisopropylsilyl
ethers and converting ketones and lactones into
their enol silyl ethers; protection of terminal alkynes; promoting
conjugate addition of alkynylzinc compounds to α,β-enones;
preparation of (triisopropylsilyl)diazomethane, participating in the following (but not limited to) reactions: Silylation of Alcohols, Formations of Enol Silyl Ethers, Alkynyltriisopropylsilanes, Conjugate Addition of Alkynylzinc Bromides, (Triisopropylsilyl)diazomethane, Triisopropylsiloxycarbonyl (Tsoc) and BIPSOP Protecting Groups for Amines, TIPS Protection for Oxazoles/Regioselective Trapping of C-2 Oxazole Anions, Benzannulation Using Triisopropylsilyl Vinyl Ketenes, Cyclization of 1-Silyloxy-1,5-diynes, Desymmetrization of Tartaric Acid Esters etc. | | 製造方法 | To 38.2 g (0.242 mol) of triisopropylsilane
at 0°C under argon is added 23.8 mL (0.266 mol) of trifluoromethanesulfonic
acid dropwise. The solution is stirred at
22°C for 16 h, at which time no further hydrogen gas evolves
(removed through a bubbler). The resulting product is distilled
through a 30-cm vacuum jacketed Vigreux column under
reduced pressure: 71.7 g (97% yield) of TIPS triflate;
bp 83–87°C/1.7 mmHg. |
|