1-[(4-Methylphenyl)sulfonyl]-1H-imidazole CAS 2232-08-8
1-[(4-Methylphenyl)sulfonyl]-1H-imidazole Basic information
| Product Name: | 1-[(4-Methylphenyl)sulfonyl]-1H-imidazole |
| Synonyms: | 1-(P-TOLUENESULFONYL)IMIDAZOLE;1-(P-TOLUENESULFONYL)-1H-IMIDAZOLE;1-TOSYLIMIDAZOLE;1-(TOLUENE-4-SULFONYL)IMIDAZOLE;Tosylimidazole;1-(p-toluenesulphonyl)imidazole;1H-IMIDAZOLE, 1-[(4-METHYLPHENYL)SULFONYL]-;1-(Toluene-4-sulfonyl)-1H-imidazole |
| CAS: | 2232-08-8 |
| MF: | C10H10N2O2S |
| MW: | 222.26 |
| EINECS: | 218-771-9 |
| Product Categories: | Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Imidazoles;Biochemistry;Condensation & Active Esterification;Condensing Agents (DNA / RNA Synthesis);Nucleosides, Nucleotides & Related Reagents;Protecting Agents, Phosphorylating Agents & Condensing Agents;Synthetic Organic Chemistry;Coupling Reagent |
| Mol File: | 2232-08-8.mol |
1-[(4-Methylphenyl)sulfonyl]-1H-imidazole Chemical Properties
| Melting point | 76-78 °C(lit.) |
| Boiling point | 409.1±38.0 °C(Predicted) |
| density | 1.3038 (rough estimate) |
| refractive index | 1.5650 (estimate) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | chloroform: soluble25mg/mL, clear, colorless to faintly yellow |
| form | Crystals or Crystalline Powder |
| pka | 1.22±0.10(Predicted) |
| color | White to slightly yellow |
| Sensitive | Moisture Sensitive |
| BRN | 612451 |
| InChI | InChI=1S/C10H10N2O2S/c1-9-2-4-10(5-3-9)15(13,14)12-7-6-11-8-12/h2-8H,1H3 |
| InChIKey | YJYMYJRAQYREBT-UHFFFAOYSA-N |
| SMILES | C1N(S(C2=CC=C(C)C=C2)(=O)=O)C=CN=1 |
| CAS DataBase Reference | 2232-08-8(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36-24/25 |
| WGK Germany | 3 |
| F | 10-21 |
| HS Code | 29332900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Aquatic Chronic 3 Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Chemical Properties | white to slightly yellow crystals |
| Uses | Alcohols to azides in one step.1 |
| Uses | 1-(p-Toluenesulfonyl)imidazole was used in the synthesis of cationic water soluble cyclodextrin, mono-6A-(1-butyl-3-imidazolium)-6A-deoxy-β-cyclodextrin chloride (BIMCD), useful in chiral separation of amino acids and anionic pharmaceuticals by capillary electrophoresis. |
| Synthesis Reference(s) | The Journal of Organic Chemistry, 45, p. 547, 1980 DOI: 10.1021/jo01291a044 |
| General Description | 1-(p-Toluenesulfonyl)imidazole converts alcohols to azides in one step. |
| Synthesis | 288-32-4 98-59-9 2232-08-8 (a) In a three-necked round-bottomed flask equipped with a charging funnel, oil collector, magnetic stirring bar and protected by argon, imidazole (5.502 g, 0.081 mol) was dissolved in 25 mL of anhydrous dichloromethane. After cooling the solution to 0°C, p-toluenesulfonyl chloride (6.78 g, 0.036 mol) dissolved in 25 mL of anhydrous dichloromethane was added slowly and dropwise. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was subsequently filtered through silica gel and the residual solid was washed with 50 mL hexane/ethyl acetate (1:1, v/v). The filtrate was concentrated in a rotary evaporator, redissolved in 6 mL of ethyl acetate and precipitation was induced by the addition of 60 mL of hexane. The resulting white solid was filtered and dried to give 7.12 g of 1-tosylimidazole (0.032 mol, 89% yield). |
| References | [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2209 - 2218 [2] Organic Syntheses, 2000, vol. 77, p. 225 - 225 [3] Tetrahedron, 2016, vol. 72, # 3, p. 379 - 391 [4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 1855 - 1858 [5] Phosphorus, Sulfur and Silicon and the Related Elements, 2011, vol. 186, # 9, p. 1867 - 1875 |
1-[(4-Methylphenyl)sulfonyl]-1H-imidazole Preparation Products And Raw materials
| Raw materials | Chloroform-->Tosyl chloride-->Imidazole-->1-(3-SULFO-4-PHENOXY)-PHENYL-3-HEPTADECYL-4-ISOPROPYL-PYRAZOLINE-5-ONE-->4-Methylbenzenesulfonhydrazide-->P-TOLUENESULFINIC ACID-->P-Toluenesulfonic anhydride-->Sodium p-toluenesulfinate-->p-Toluenesulfonic acid-->1,1'-Carbonyldiimidazole |
| Preparation Products | Benzene, [(2,2,2-trifluoroethoxy)methyl]--->1H-Isoindol-1-one, 3-hydroxy--->Chlorotrimethylsilane |
