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| | 4,4'-Di-tert-butyl-2,2'-bipyridine Basic information | | Reaction |
| Product Name: | 4,4'-Di-tert-butyl-2,2'-bipyridine | | Synonyms: | 4,4'-Di-tert-butyl-2,2'-dipyidyl;l-2,2'-bipyridine;4 4'-DI-TERT-BUTYL-2 2'-DIPYRIDYL 98;4,4'-Di-O-tert-butyl-2,2'-bypyridine;4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine;2,2'-Bipyridine,4,4'-bis(1,1-diMethylethyl)-;4,4'-Di-tert-butyl-2,2'-dipyridyl 98%;4,4'-Di-tert-butyl-2,2'-dipyridine | | CAS: | 72914-19-3 | | MF: | C18H24N2 | | MW: | 268.4 | | EINECS: | | | Product Categories: | Heterocycle-Pyridine series;Achiral Nitrogen;Py-N;C9 to C46;Heterocyclic Building Blocks;Pyridines | | Mol File: | 72914-19-3.mol |  |
| | 4,4'-Di-tert-butyl-2,2'-bipyridine Chemical Properties |
| Melting point | 159-161 °C(lit.) | | Boiling point | 395.4±42.0 °C(Predicted) | | density | 0.977 | | storage temp. | Inert atmosphere,Room Temperature | | solubility | DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | | form | crystal | | pka | 5.15±0.30(Predicted) | | color | white | | Stability: | hygroscopic | | InChI | InChI=1S/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 | | SMILES | C1(C2=NC=CC(C(C)(C)C)=C2)=NC=CC(C(C)(C)C)=C1 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | TSCA | No | | HS Code | 29333990 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 3 Dermal
Acute Tox. 3 Oral |
| | 4,4'-Di-tert-butyl-2,2'-bipyridine Usage And Synthesis |
| Reaction |
- Ligand for the iridium-catalyzed borylation of arenes
- Ligand for the iridium-catalyzed synthesis of arylboronic acids and aryl trifluoroborates
- Ligand for the nickel-catalyzed hydroxycarboxylation of 1,2-dienes by reaction carbon dioxide and oxygen
- Ligand for the iridium-catalyzed meta borylation followed by halogenation of 1,3-disubstituted arenes
- Ligand for the iridium-catalyzed silyl-directed ortho-borylation of arenes
- Ligand for the iridium-catalyzed silane borylation followed by aryl borylation
- Ligand for the iridium-catalyzed microwave-accelerated borylation of aromatic C-H bonds
- Ligand for the iridium-catalyzed silyl-directed borylation of indoles
- Ligand for the nickel-catalyzed synthesis of functionalized dialkyl ketones from carboxylic acids and alkyl halides
- Ligand for the iron-catalyzed arylation of heterocycles
| | Chemical Properties | white cyrstalline powder | | Uses |
4,4'-Di-tert-butyl-2,2'-dipyridyl acts as a reagent in the preparation, antiproliferative and cytotoxic activity of apoptotic ruthenium nitrogen heterocyclic complexes via combinatorial library synthesis.
| | Synthesis | In this embodiment, the synthesis of 4,4'-di-tert-butyl-2,2'-bipyridine from 4-tert-butylpyridine was investigated. This was done as follows: 4-tert-butylpyridine (0.5 mmol) was reacted with SD (1 to 2 molar equivalents) in THF (2 to 4 mL) at a reaction temperature of 50°C for a reaction time of 1 to 24 hours. Upon completion of the reaction, the reaction products were isolated and purified according to the method of Example 1 to obtain 4,4'-di-tert-butyl-2,2'-bipyridine (target product), 4-tert-butyl-1,4-dihydropyridine (byproduct 1), and 4,4',4''-tri-tert-butyl-2,2':6',2''-tripyridine (byproduct 3), and the respective yields were calculated. Also, the recovery of unreacted 4-tert-butylpyridine was calculated. The experimental results showed that the highest yield of 4,4'-di-tert-butyl-2,2'-bipyridine was achieved under the optimal conditions (0.5 mmol of 4-tert-butylpyridine reacted with 1 molar equivalent of SD in 4 mL of THF at 50 °C for 6 h) and no by-products were generated. In addition, the use of 2 molar equivalents of SD resulted in a lower yield and material balance. Comparison with Example 1 shows that decreasing the concentration of 4-tert-butylpyridine and SD relative to THF contributes to higher yields. | | References | [1] Patent: US2018/282278, 2018, A1. Location in patent: Paragraph 0057; 0127-0130
[2] Helvetica Chimica Acta, 1980, vol. 63, # 6, p. 1675 - 1702
[3] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 2000, # 1, p. 63 - 68
[4] Inorganica Chimica Acta, 2011, vol. 365, # 1, p. 127 - 132
[5] Synthesis (Germany), 2013, vol. 45, # 22, p. 3099 - 3102 |
| | 4,4'-Di-tert-butyl-2,2'-bipyridine Preparation Products And Raw materials |
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