N-Phenyl-bis(trifluoromethanesulfonimide) CAS 37595-74-7
Introduction：Basic information about N-Phenyl-bis(trifluoromethanesulfonimide) CAS 37595-74-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
N-Phenyl-bis(trifluoromethanesulfonimide) Basic information
| Product Name: | N-Phenyl-bis(trifluoromethanesulfonimide) |
| Synonyms: | phenyltrifluoromethanesulfonimide;N-PHENYLBIS(TRIFLUOROMETHANESULFONIMIDE);N-PHENYLBIS(TRIFLUOROMETHANESULPHONIMIDE);N-PHENYLTRIFLUOROMETHANESULFONIMIDE;N-PHENYLTRIFLUOROMETHANESULPHONIMIDE;N,N-BIS(TRIFLUOROMETHYLSULFONYL)ANILINE;1,1,1-TRIFLUORO-N-PHENYL-N-[(TRIFLUOROMETHYL)SULFONYL]METHANESULFONAMIDE;N-Phenylbis(trifluoromethanesulphonimide), Phenyl triflimide |
| CAS: | 37595-74-7 |
| MF: | C8H5F6NO4S2 |
| MW: | 357.25 |
| EINECS: | 609-445-0 |
| Product Categories: | API intermediates;37595-74-7 |
| Mol File: | 37595-74-7.mol |
N-Phenyl-bis(trifluoromethanesulfonimide) Chemical Properties
| Melting point | 100-102 °C(lit.) |
| Boiling point | 305.3±52.0 °C(Predicted) |
| density | 1.766±0.06 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | Soluble in methanol. Slightly soluble in chloroform and ethyl acetate. |
| pka | -13.12±0.50(Predicted) |
| form | Crystals or Crystalline Powder |
| color | White or colorless |
| Sensitive | Moisture Sensitive |
| BRN | 1269141 |
| Stability: | Moisture Sensitive |
| InChI | InChI=1S/C8H5F6NO4S2/c9-7(10,11)20(16,17)15(6-4-2-1-3-5-6)21(18,19)8(12,13)14/h1-5H |
| InChIKey | DIOHEXPTUTVCNX-UHFFFAOYSA-N |
| SMILES | C(F)(F)(F)S(N(C1=CC=CC=C1)S(C(F)(F)F)(=O)=O)(=O)=O |
| CAS DataBase Reference | 37595-74-7(CAS DataBase Reference) |
| NIST Chemistry Reference | N-phenyltrifluoromethanesulfonimide(37595-74-7) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| F | 21 |
| TSCA | No |
| HazardClass | IRRITANT |
| HS Code | 29242100 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Description | N-Phenylbis(trifluoromethanesulfonimide) acts as a mild triflating reagent as well as a transparent strong electron-withdrawing p-type dopant in carbon nanotubes. It is also employed as a reactant for the preparation of amphoteric alfa-boryl aldehydes. It plays an important role in the enantioselective synthesis of the core ring skeleton of leucosceptroids A-D and in steroselective sulfoxidation. |
| Chemical Properties | white to off-white crystalline powder |
| Uses | N-Phenylbis(trifluoromethanesulfonamide) is used in the enantioselective synthesis of β-amino acids via the Mannich reaction. Used in the synthesis of sphingosine 1-phosphate-1 receptor agonists useful in pharmaceutical application. |
| Uses | Acts as a transparent strong electron-withdrawing p-type dopant in carbon nanotubes Reactant for: Synthesis of amphoteric alpha-boryl aldehydes Enantioselective synthesis of core ring skeleton of leucosceptroids A-D Stereoselective synthesis of monoamine reuptake inhibitor NS9544 acetate Stereoselective sulfoxidation |
| Synthesis | Add methylene chloride, aniline, 4-dimethylaminopyridine (DMAP), and triethylamine to a reactor equipped with a thermometer, distillation device, and mechanical stirring. When the vacuum of the reactor is evacuated to -0.095MPa and cooled to -40°C, trifluoromethanesulfonyl fluoride gas is introduced and then stirred at -20°C ~ 0°C and 0.02MPa ~ 0.1MPa reaction pressure, and react for 6 hours Finally, the excess trifluoromethanesulfonyl fluoride gas in the reactor is released and collected by cooling. After the inside of the reactor is brought to normal pressure, 500 mL of water is added, and the liquid is separated. A light yellow solid is obtained after the organic phase is heated to 40°C and methylene chloride is distilled. The light yellow solid is recrystallized with toluene to obtain 650g of white crystal N-Phenyl-bis(trifluoromethanesulfonimide). |
| References | [1] Patent: US2012/316204, 2012, A1. Location in patent: Page/Page column 7-8 [2] Patent: WO2015/23967, 2015, A2. Location in patent: Paragraph 0163; 0171 [3] Patent: WO2016/27284, 2016, A2. Location in patent: Page/Page column 69-70 [4] Tetrahedron Letters, 1973, # 46, p. 4607 - 4610 [5] Patent: WO2015/112441, 2015, A1. Location in patent: Page/Page column 58 |
N-Phenyl-bis(trifluoromethanesulfonimide) Preparation Products And Raw materials
| Raw materials | Ethanol-->Sodium hydroxide-->Tetrahydrofuran-->Dichloromethane-->Potassium carbonate-->Magnesium sulfate-->Triethylamine-->Sodium chloride-->Sodium hydride-->Aniline-->Trifluoromethanesulfonic anhydride-->Trifluoromethanesulfonyl chloride |
| Preparation Products | 1-Boc-4-methanesulfonyloxypiperidine-->2-(triMethylsilyl)ethyl 4-(trifluoroMethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate-->1-CYCLOHEXEN-1-YL TRIFLUOROMETHANE--->Methyl 3-((Trifluoromethylsulfonyl)oxy)phenylacetate |
