72914-19-3
4,4'-Di-tert-butyl-2,2'-bipyridine
CAS: 72914-19-3
Molecular Formula: C18H24N2
72914-19-3 - Names and Identifiers
| Name | 4,4'-Di-tert-butyl-2,2'-bipyridine |
| Synonyms | dbbpy l-2,2'-bipyridine 4,4'-Di-tert-butyl-2,2'-dipyidyl 4,4'-Di-tert-butyl-2,2'-dipyridyl 4,4'-Di-tert-butyl-2,2'-bipyridine 4,4'-Di-O-tert-butyl-2,2'-bypyridine 4 4'-DI-TERT-BUTYL-2 2'-DIPYRIDYL 98 2,2'-Bipyridine,4,4'-bis(1,1-diMethylethyl)- 2,2'-bipyridine, 4,4'-bis(1,1-dimethylethyl)- 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine |
| CAS | 72914-19-3 |
| InChI | InChI=1/C18H24N2/c1-17(2,3)13-7-9-19-15(11-13)16-12-14(8-10-20-16)18(4,5)6/h7-12H,1-6H3 |
| InChIKey | TXNLQUKVUJITMX-UHFFFAOYSA-N |
72914-19-3 - Physico-chemical Properties
| Molecular Formula | C18H24N2 |
| Molar Mass | 268.4 |
| Density | 0.977 |
| Melting Point | 159-161°C(lit.) |
| Boling Point | 395.4±42.0 °C(Predicted) |
| Flash Point | 150.2°C |
| Solubility | DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) |
| Vapor Presure | 4.21E-06mmHg at 25°C |
| Appearance | crystal |
| Color | white |
| pKa | 5.15±0.30(Predicted) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Stability | hygroscopic |
| Refractive Index | 1.522 |
| MDL | MFCD01863731 |
72914-19-3 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| TSCA | No |
| HS Code | 29333990 |
72914-19-3 - Reference Information
| Application | 4,4 '-di-tert-butyl -2,2'-dipyridine is an organic intermediate, it can be prepared from 4-(tert-butyl)-2-(tert-butyldimethylsilyl) pyridine and 2-bromo-4-(tert-butyl) pyridine by Hiyama-Denmark cross-coupling reaction. |
| preparation | general procedure A: to a 10 mL vial with a Teflon spacer and magnetic stir bar was added the corresponding heterocyclic ring (0.5 mmol,1.0 EQ), the corresponding silane (2.5 mmol,5.0 EQ),Na2S2O8(1.0mmol, (2.0)) and Ir(ppy)2(dtbpy)PF6(0.005 mmol,0.01 EQ). The vial was sealed and placed in atmosphere, then DMSO / DCE(1:1)(5 mL,0.1 M) was added. The reaction was placed between 2 x 23 W fluorescent lamps (about 5 cm per lamp) and irradiated for 24 hours. The reaction mixture was diluted with saturated aqueous NaHCO3, extracted with ethyl acetate (3 x 20 mL) and the combined organic extracts were washed with brine (30mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel using the indicated solvent system to give the desired product. 4-(tert-butyl)-2-(tert-butyldimethylsilyl) pyridine (3o): According to the general method A,4-(tert-butyl) pyridine (0.5 mmol,1 equiv), tert-butyldimethylsilane (290 mg ,2.5 mmol,5 equiv),Na2S2O8(238 mg,1.0 mmol,2.0 equiv),Ir(ppy)2(dtbpy)PF6(4.6 mg,0.005 mmol,0.01 equiv) and 5mL DMSO / DCE(1: 1)(0.1 M) were used. The product was isolated by flash chromatography (2% ethyl acetate/hexanes) as a colorless oil (90mg,72%). General method D for Hiyama-Denmark cross-coupling of heteroarylsilane products: to a 10 mL vial equipped with a Teflon spacer and a magnetic stir bar was added the corresponding arylsilane (0.5 mmol,1.0 EQ), the corresponding aryl iodide or bromide (1.0mmol,2 eq),Pd(Ph3P)4(0.025mmol,0.05 EQ) and Ag2O(0.5 mmol,1 eq). The vial was sealed and placed under a nitrogen atmosphere, then anhydrous DMF(5mL,0.1M) and TBAF(0.25mL,0.5 equiv., 1mmol / L in THF) were added. The reaction was heated at 90 °c for 4 hours. The reaction mixture was diluted with water, extracted with ethyl acetate (3 x 20ml) and the combined organic extracts were washed with brine (30ml), dried over anhydrous Na2SO4 and concentrated in vacuo. The crude S35 product was purified by flash chromatography on silica gel using the indicated solvent system to give the desired product. 4,4 '-di-tert-butyl -2,2'-bipyridine (15): follow the general procedure for Hiyama-Denmark cross-coupling D with 4-(tert-butyl)-2-(tert-butyldimethylsilyl) pyridine 3o and 2-bromo-4-(tert-butyl) pyridine were reacted and the crude mixture was purified by flash column chromatography (50% ethyl acetate/hexane) to give the title compound as a white solid (74mg,55%). |
Last Update：2024-04-10 22:29:15
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Mobile: 18021002903
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