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| Product Name: | 2,6-DI-TERT-BUTYLPYRIDINE | | Synonyms: | Pyridine, 2,6-bis(1,1-dimethylethyl)-;Pyridine, 2,6-di-tert-butyl-;2,6-DI-TERT-BUTYLPYRIDINE;2,6-Bis(1,1-dimethylethyl)pyridine;2,6-Di-tert-butylpyridine ,96%;2,6-DI-TERT-BUTYLPYRIDINE 97%;2,6-DI-TERT-BUTYLPYRIDINE, >=97%;2,6-Di-tert-butylpyridine, 97% 25GR | | CAS: | 585-48-8 | | MF: | C13H21N | | MW: | 191.31 | | EINECS: | 209-557-6 | | Product Categories: | Pyridines, Pyrimidines, Purines and Pteredines;Heterocyclic Compounds;C9 to C46;Heterocyclic Building Blocks;Pyridines | | Mol File: | 585-48-8.mol |  |
| | 2,6-DI-TERT-BUTYLPYRIDINE Chemical Properties |
| Melting point | 2°C(lit.) | | Boiling point | 100-101 °C/23 mmHg (lit.) | | density | 0.852 g/mL at 25 °C (lit.) | | refractive index | 1.472-1.474 | | Fp | 72 °C | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Liquid | | pka | 3.58(at 25℃) | | color | Clear yellow | | Specific Gravity | 0.852 | | Water Solubility | Miscible with alcohol, acetone, and hexane. Immiscible with water. | | Merck | 14,3036 | | BRN | 125886 | | Dielectric constant | 3.3900000000000001 | | Stability: | Stable. Combustible. Incompatible with strong acids, strong oxidizing agents. | | InChIKey | UWKQJZCTQGMHKD-UHFFFAOYSA-N | | CAS DataBase Reference | 585-48-8(CAS DataBase Reference) |
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ACROS
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| | 2,6-DI-TERT-BUTYLPYRIDINE Usage And Synthesis |
| Overview | 2,6-Di-tert-butylpyridine is a weak base used in the preparation of 2, 6-di-tert-butylpyridine hydrotriflate. It is used as a proton scavenger to check the progress of the living polymerization of isobutylene. It is associated with cerric ammonium nitrate and used in the alfa-enolation of aldehydes. It is involved in the preparation of vinyl triflate using polymer-bound 2,6-di-tert-butylpyridine. Since it was first synthesized by Brown and Kanner[1], 2,6-di-tert-butylpyridine has attracted the interest of many researchers because of its unusually low basicity: with its two-alkyl substituents, DTBP is nevertheless a weaker base than unsubstituted pyridine in aqueous solution. Brown and Kanner[1] and others[2] proposed that the abnormally low basicity of DTBP was caused by steric hindrance to hydration of DTBPH+. Recent determinations of gas-phase proton affinities of DTBP and other alkyl-substituted pyridines showed that the basicity of DTBP in the gas phase was normal[2, 3], which confirmed that its weak basicity in water was due to solvent effects on DTBP and (or) DTBPH+. A complete analysis of the thermodynamic cycles linking the protonation processes of DTBP and other pyridines in the gas phase and in aqueous solution led Arnett and Chawla[2] to conclude that there was indeed some hindrance to the hydration of DTBPH+ as reflected in its abnormally low enthalpy of hydration. However, more recently Hopkins et al.[3], after investigating the protonation of additional tertbutylpyridines and repeating the thermodynamic determinations of Amett and Chawla[2] of DTBP, concluded from their new data that the hydration enthalpy of DTBPH+ was normal but that the corresponding entropy was abnormal; they suggested that the rotation of the water molecule attached to DTBPH+ and of -CMe3 was restricted. These results and conclusions were in agreement with the gas phase studies of Moet-Ner and Sieck[4] on the attachment of one water molecule to a series of pyridinium cations including DTBPH+.
| | Reference |
- H. C. BROWN and B. KANNERJ. Am. Chem. Soc. 75, 3865 (1953).
- E. M. ARNETT and B. CHAWLAJ. Am. Chem. Soc. 101, 7141 (1979).
- H.P.HOPKINSD,.V.JAHAGIRDAP.RS,.MOULIKD,.H.AUE, H. M. WEBB,W. R. DAVIDSON and M. D. PEDLEY. J.. Am. Chem. Soc. 106,4341 (1984).
- M. MEOT-NEaRnd L. W. SIECK J. Am. Chem. Soc. 105, 2956 (1983)
| | Chemical Properties | dark brown liquid | | Uses | 2,6-Di-tert-butylpyridine was used as proton trapping agent to investigate the living polymerization of isobutylene. It was also used with cerric ammonium nitrate in the α-enolation of aldehydes leading to 1,4-dicarbonyl systems. | | Uses | 2,6-Di-tert-butylpyridine is used in the preparation of 2, 6-di-tert-butylpyridine hydrotriflate. It is used as a proton scavenger to check the progress of the living polymerization of isobutylene. It is associated with cerric ammonium nitrate and used in the alfa-enolation of aldehydes. It is involved in the preparation of vinyl triflate using polymer-bound 2,6-di-tert-butylpyridine. | | Definition | ChEBI: 2,6-di-tert-butylpyridine is a member of pyridines. | | General Description | Reactivity of 2,6-di-tert-butylpyridine with iron(III) tetraphenylporphyrin pi-cation radical has been examined by proton NMR spectroscopy. Reaction of 2,6-di-tert-butylpyridine with methyl iodide and methyl fluorosulfonate under high pressure has been reported. | | Purification Methods | Redistil it from KOH pellets. [Beilstein 20 III/IV 2868.] |
| | 2,6-DI-TERT-BUTYLPYRIDINE Preparation Products And Raw materials |
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