2-ETHOXYETHYL P-TOLUENESULFONATE CAS#: 17178-11-9; 凯望编码 (ChemWhat Code): 162773
Identification
| 英文名 | 2-ETHOXYETHYL P-TOLUENESULFONATE |
| IUPAC Name | 2-ethoxyethyl 4-methylbenzenesulfonate |
| 分子结构 |  |
| CAS编号 | 17178-11-9 |
| MDL Number | MFCD00088078 |
| 别名 | 2-ethoxyethyl 4-methylbenzenesulfonate 17178-11-9 2-ETHOXYETHYL P-TOLUENESULFONATE 2-ethoxyethyl 4-methylbenzene-1-sulfonate p-toluenesulfonic-acid-(2-ethoxyethyl)-ester SCHEMBL244712 DTXSID10399598 (2-ethoxy)ethyl p-toluenesulphonate 2-ethoxyethyl4-methylbenzenesulfonate AKOS005111037 CS-0257595 G30161 EN300-6740858 |
| 分子式 | C11H16O4S |
| 分子量 | 244.31 |
| InChI | InChI=1S/C11H16O4S/c1-3-14-8-9-15-16(12,13)11-6-4-10(2)5-7-11/h4-7H,3,8-9H2,1-2H3 |
| InChI Key | HXXNTEDKEYTYPD-UHFFFAOYSA-N |
| Isomeric SMILES | CCOCCOS(=O)(=O)C1=CC=C(C=C1)C |
Physical Data
| Appearance | Liquid |
| Melting Point, °C |
| 15 – 16 |
| 18.5 |
| Boiling Point, °C | Pressure (Boiling Point), Torr |
| 145 – 146 | 0.5 |
| 158 – 162 | 1 |
| 122 | 0.1 |
| 157 – 158 | 2 |
| 186 – 187 | 3 |
| Density, g·cm-3 | Reference Temperature, °C | Measurement Temperature, °C |
| 1.1677 | 25 | 25 |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C |
| Chemical shifts, Spectrum | 1H | dimethylsulfoxide-d6 | 25 |
| Chemical shifts | 1H | chloroform-d1 | |
| Chemical shifts | 1H | CDCl3 | |
| 1H | CDCl3 | ||
| Chemical shifts | 1H | CDCl3 |
Route of Synthesis (ROS)
| Conditions | Yield |
| With pyridine at 0℃; | 100% |
| With sodium hydroxide In tetrahydrofuran; water | 85% |
| With triethylamine In dichloromethane at 20℃; for 4h; Experimental Procedure 15.1 Step 1 2-ethoxy ethyl-4-methyl-phenyl-sulfonate 15b Under room temperature, the ethylene glycol monoethyl ether is 15a (10.0g, 111 . 0mmol) dissolved in dichloromethane (100 ml) solution, then in the reaction system by adding triethylamine (31 ml, 224mmol) and to toluene sulfonyl chloride (19.04g, 99 . 87mmol), reaction 4 hours. Concentrate under reduced pressure to remove the solvent, to the residue add 100 ml ethyl acetate and 100 ml of water, stirring 2 minutes, liquid separation, the organic phase separated saturated salt water for washing (100 ml), anhydrous sodium sulfate for drying, filtering, the filtrate concentrated under reduced pressure, the residue is purified by silica gel column chromatography [ethyl acetate/petroleum ether (v/v)=1/10], to obtain title compound 15b (22.0g, light yellow oily matter), yield: 81.1%. | 81.1% |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Warning |
| GHS Hazard Statements | H302 (97.44%): Harmful if swallowed [Warning Acute toxicity, oral] |
| Precautionary Statement Codes | P264, P270, P301+P317, P330, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | Store at 2~8° for long time. |
| Storage | Store at 2~8° for long time. |
| Shelf Life | 1 year |
| Market Price |
| Druglikeness | |
| Lipinski rules component | |
| 分子量 | 244.312 |
| logP | 1.254 |
| HBA | 4 |
| HBD | 0 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 60.98 |
| Rotatable Bond (RotB) | 6 |
| Matching Veber Rules | 2 |
| Use Pattern |
| 2-Ethoxyethyl 4-methylbenzenesulfonate is an important intermediate in the synthesis of Bilastine, an antihistamine used for treating allergic rhinitis and urticaria. During the synthesis of complex molecules like Bilastine, certain functional groups need to be temporarily protected to prevent them from reacting prematurely or undesirably. 2-Ethoxyethyl 4-methylbenzenesulfonate can act as a protecting group for hydroxyl or amino groups, allowing chemists to selectively modify other parts of the molecule. 2-ethoxyethyl 4-methylbenzenesulfonate can enhance the overall yield and purity of the final product. 2-ethoxyethyl 4-methylbenzenesulfonate is crucial in the synthesis of Bilastine as it acts as both a protecting group and a leaving group, ensuring the correct assembly and high purity of the final pharmaceutical product. |
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