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Published TCIMAIL newest issue No.197
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CAS RN: 98-59-9 | Product Number: T0272
p-Toluenesulfonyl Chloride
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Purity: >99.0%(GC)
Synonyms:
- Tosyl Chloride
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
|---|---|---|---|---|
| 25G |
32,00 €
|
19 | ≥60 |
|
| 500G |
54,00 €
|
≥60 | 35 |
|
*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).
| Product Number | T0272 |
| Purity / Analysis Method | >99.0%(GC) |
| Molecular Formula / Molecular Weight | C__7H__7ClO__2S = 190.64 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature | Room Temperature (Recommended in a cool and dark place, <15°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Moisture Sensitive |
| CAS RN | 98-59-9 |
| Reaxys Registry Number | 607898 |
| PubChem Substance ID | 87576251 |
| SDBS (AIST Spectral DB) | 3090 |
| Merck Index (14) | 9534 |
| MDL Number | MFCD00007450 |
Specifications
| 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 |
Properties (reference)
| Melting Point | 68 °C |
| Boiling Point | 146 °C/15 mmHg |
GHS
| Pictogram |
|
| Signal Word | Danger |
| Hazard Statements | H314 : Causes severe skin burns and eye damage. H290 : May be corrosive to metals. |
| Precautionary Statements | P260 : Do not breathe dust. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection. P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water. P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. 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. |
Related Laws:
| EC Number | 202-684-8 |
Transport Information:
| UN Number | UN3261 |
| Class | 8 |
| Packing Group | III |
| HS Number | 2904100090 |
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.
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