| Identification | More | [Name]
2,6-DI-TERT-BUTYLPYRIDINE | [CAS]
585-48-8 | [Synonyms]
2,6-DI-T-BUTYLPYRIDINE
2,6-DI-TERT-BUTYLPYRIDINE
Pyridine, 2,6-bis(1,1-dimethylethyl)-
Pyridine, 2,6-di-tert-butyl-
2,6-DI-TERT-BUTYLPYRIDINE, >=97%
2,6-DI-TERT-BUTYLPYRIDINE 97% | [EINECS(EC#)]
209-557-6 | [Molecular Formula]
C13H21N | [MDL Number]
MFCD00006306 | [Molecular Weight]
191.31 | [MOL File]
585-48-8.mol |
| Chemical Properties | Back Directory | [Appearance]
dark brown liquid | [Melting point ]
2°C(lit.) | [Boiling point ]
100-101 °C/23 mmHg (lit.) | [density ]
0.852
| [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 | [Stability:]
Stable. Combustible. Incompatible with strong acids, strong oxidizing agents. | [Water Solubility ]
Miscible with alcohol, acetone, and hexane. Immiscible with water. | [Merck ]
3036 | [BRN ]
125886 | [Dielectric constant]
3.3900000000000001 | [InChIKey]
UWKQJZCTQGMHKD-UHFFFAOYSA-N | [CAS DataBase Reference]
585-48-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing . | [RIDADR ]
3267 | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HS Code ]
29339900 |
| Questions And Answer | Back Directory | [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)
|
| Hazard Information | Back Directory | [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.] |
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