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Thermo Scientific Chemicals
2,6-Di-tert-butyl-4-methylpyridine, 97%
CAS: 38222-83-2 | C14H23N | 205.35 g/mol
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CAS38222-83-2
IUPAC Name2,6-di-tert-butyl-4-methylpyridine
Molecular FormulaC14H23N
InChI KeyHVHZEKKZMFRULH-UHFFFAOYSA-N
SMILESCC1=CC(=NC(=C1)C(C)(C)C)C(C)(C)C
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規格
規格表
規格表Appearance (Color)White to pale yellow or brown
FormCrystals or powder or crystalline powder or crystalline chunks or fused/lumpy solid
Assay (GC)≥96.0%
Refractive Index1.4745-1.4795 as melt
2,6-Di-tert-butyl-4-methylpyridine is used for the generation of enol triflates from ketones using trifluoromethanesulfonic anhydride. It is also used in the synthesis of 1,2-dihydro-2-silanaphthalene derivatives, as base in PtCl4-catalyzed cyclization reactions of homopropargyl azide derivatives and in diastereoselective synthesis of β-thiomannopyranosides.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
2,6-Di-tert-butyl-4-methylpyridine is used for the generation of enol triflates from ketones using trifluoromethanesulfonic anhydride. It is also used in the synthesis of 1,2-dihydro-2-silanaphthalene derivatives, as base in PtCl4-catalyzed cyclization reactions of homopropargyl azide derivatives and in diastereoselective synthesis of β-thiomannopyranosides.
Solubility
Sparingly soluble in water. Soluble in ethanol, acetic acid and diethyl ether.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature is 2 - 8°C. Store under inert gas. It is sensitive to air and light.
2,6-Di-tert-butyl-4-methylpyridine is used for the generation of enol triflates from ketones using trifluoromethanesulfonic anhydride. It is also used in the synthesis of 1,2-dihydro-2-silanaphthalene derivatives, as base in PtCl4-catalyzed cyclization reactions of homopropargyl azide derivatives and in diastereoselective synthesis of β-thiomannopyranosides.
Solubility
Sparingly soluble in water. Soluble in ethanol, acetic acid and diethyl ether.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature is 2 - 8°C. Store under inert gas. It is sensitive to air and light.
RUO – Research Use Only
General References:
- D Crich.; H Li. Direct stereoselective synthesis of beta-thiomannosides. Journal of Organic Chemistry. 2000, 65 (3), 801-805.
- Hidekazu Arii.; Takashi Kurihara.; Kunio Mochida.; Takayuki Kawashima.Silylium ion-promoted dehydrogenative cyclization: synthesis of silicon-containing compounds derived from alkynes. Chemical Communications. 2014, 50 (50), 6649-6652.
- Sterically-hindered, non-nucleophilic base.
- Recommended base for the generation of enol triflates from ketones using Trifluoromethanesulfonic anhydride, A11767: J. Org. Chem., 54, 2886 (1989). For examples, see: Org. Synth. Coll., 8, 97, 126 (1993). For comparison with other hindered bases in peptide coupling reactions, see: J. Org. Chem., 61, 2460 (1996). See also Appendix 6.