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CAS RN: 98-59-9 | 产品编码: T0272
p-Toluenesulfonyl Chloride
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技术规格
| 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 |
物性（参考值）
| 熔点 | 68 °C |
| 沸点 | 146 °C/15 mmHg |
GHS
| 象形图 |
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| 信号词 | Danger |
| 危险性说明 | H314 : Causes severe skin burns and eye damage. H402 : Harmful to aquatic life. H290 : May be corrosive to metals. |
| 防范说明 | 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. |
相关法规
运输信息
| UN编号 | UN3261 |
| 类别 | 8 |
| 包装类别 | III |
| HS编码* | 2904.10-000 |
应用
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.
应用
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
参考文献
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