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CAS RN: 98-59-9 | 產品號碼: T0272
p-Toluenesulfonyl Chloride
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* TCI會時常優化儲存條件,儲存溫度請以在線目錄為準，敬請留意。
| 產品號碼 | T0272 |
| 純度/分析方法 | >99.0%(GC) |
| 分子式 / 分子量 | C__7H__7ClO__2S = 190.64 |
| 外觀與形狀（20°C） | Solid |
| 儲存條件 | Room Temperature (Recommended in a cool and dark place, <15°C) |
| 儲存在惰性氣體下 | Store under inert gas |
| 應避免的情況 | Moisture Sensitive |
| CAS RN | 98-59-9 |
| Reaxys-RN | 607898 |
| PubChem Substance ID | 87576251 |
| SDBS (AIST Spectral DB) | 3090 |
| Merck Index(14) | 9534 |
| MDL編號 | MFCD00007450 |
產品規格
| Appearance | White to Light yellow powder to crystal |
| Purity(GC) | min. 99.0 % |
| Purity(Argentometric Titration) | min. 98.0 % |
| Melting point | 67.0 to 71.0 °C |
| NMR | confirm to structure |
性質
| 熔點 | 68 °C |
| 沸點 | 146 °C/15 mmHg |
GHS
| 圖形表示 |
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| 信號詞 | Danger |
| 危險性說明 | H314 : Causes severe skin burns and eye damage. H402 : Harmful to aquatic life. H290 : May be corrosive to metals. |
| 防範說明 | P501 : Dispose of contents/ container to an approved waste disposal plant. P273 : Avoid release to the environment. P260 : Do not breathe dusts or mists. P234 : Keep only in original container. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection. P390 : Absorb spillage to prevent material damage. P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower. P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P363 : Wash contaminated clothing before reuse. P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor. P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor. P406 : Store in corrosive resistant container with a resistant inner liner. P405 : Store locked up. |
相關法規
運輸資料
| UN編號 | UN3261 |
| 類別 | 8 |
| 包裝類別 | III |
| HS編碼* | 2904.10-000 |
Application
TCI Practical Example: Tosylation of Hydroxy Group Using TsCl
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Used Chemicals
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Procedure
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Triethylamine (1.23 mL, 7.64 mmol, 1.5 eq.), DMAP (23.1 mg, 0.19 mmol, 0.04 eq.), and TsCl (1.17 g, 6.11 mmol, 1.2 eq.) were added to a solution of diethylene glycol monobenzyl ether (1.00 g, 5.10 mmol) in dichloromethane (12.1 mL) at room temperature. The reaction mixture was stirred for overnight. The reaction mixture was quenched with 1 mol/L HCl (10 mL) and extracted with dichloromethane (3 x 10 mL). The organic layer washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate:hexane = 10:90 – 25:75 on silica gel), giving 1 as a colorless liquid (1.58 g, 89% yield).
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Experimenter’s Comments
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The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:1, Rf = 0.55).
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Analytical Data
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Tosylate 1
1H NMR (270 MHz, CDCl3); δ 7.80 (d, J = 8.4 Hz, 2H), 7.39-7.29 (m, 7H), 4.54 (s, 2H), 4.17 (t, J = 4.6 Hz, 2H), 3.70 (brt, J = 4.9 Hz, 2H), 3.62 (m, 2H), 3.56 (m, 2H), 2.43 (s, 3H).
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Other Reference
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- A Synthesis of Acetamidines
- H. Nakatsuji, K. Ueno, T. Misaki, Y. Tanabe, Org. Lett. 2008, 10, 2131.
- H. Nakatsuji, H. Nishikado, K. Ueno, Y. Tanabe, Org. Lett. 2009, 11, 4258.
Application
Stereocomplementary Enol Tosylation
Typical Procedure (Enol Tosylation of α-Formyl Esters) Method A: An α-formyl ester (1.00 mmol) in toluene (1 mL) and TsCl (228 mg, 1.20 mmol) in toluene (1 mL) are successively added dropwise to a stirred solution of N-methylimidazole (NMI) (99 mg, 1.20 mmol) and Et3N (121 mg, 1.20 mmol) in toluene (1 mL) at 0－5 °C under an Ar atmosphere, and the mixture is stirred at the same temperature for 1 h. Water is added to the mixture, which is extracted twice with AcOEt. The combined organic phase is washed with brine, dried (Na2SO4), and concentrated. The residue is purified by SiO2 column chromatography (hexane : AcOEt = 25 : 1－5 : 1) to give the desired (E)-enol tosylates. Method B: An α-formyl ester (1.00 mmol) in toluene (1 mL), TsCl (228 mg, 1.20 mmol) in toluene (1 mL), and NMI (99 mg, 1.20 mmol) are successively added dropwise to a stirred suspension of LiOH powder (anhydrous; 29 mg, 1.20 mmol) in toluene (1 mL) at 0－5 °C under an Ar atmosphere, and the mixture is stirred at the same temperature for 1 h. A workup similar to that of method A gives the desired (Z)-enol tosylates.
References
考研文獻
文章/手冊
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產品規格
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