249505

2,6-Di-tert-butyl-4-methylpyridine

98%

• Synonym(s): 2,6-Bis(1,1-dimethylethyl)-4-methylpyridine, 2,6-Bis(tert-butyl)-4-methylpyridine, 2,6-Ditert-butyl-4-methylpyridine, 4-Methyl-2,6-di-tert-butylpyridine
• Empirical Formula (Hill Notation): C₁₄H₂₃N
• CAS Number: 38222-83-2
• Molecular Weight: 205.34
• Beilstein: 130503
• EC Number: 253-834-4
• MDL number: MFCD00006305
• UNSPSC Code: 12352100
• PubChem Substance ID: 24855001
• NACRES: NA.22

Properties

• Assay: 98%
• form: solid
• refractive index: n20/D 1.4763 (lit.)
• bp: 233 °C (lit.)
• mp: 33-36 °C (lit.)
• solubility: ethanol: soluble 5%, clear to slightly hazy, colorless to dark yellow
• storage temp.: 2-8°C
• SMILES string: Cc1cc(nc(c1)C(C)(C)C)C(C)(C)C
• InChI: 1S/C14H23N/c1-10-8-11(13(2,3)4)15-12(9-10)14(5,6)7/h8-9H,1-7H3
• InChI key: HVHZEKKZMFRULH-UHFFFAOYSA-N

Description

General description

2,6-Di-tert-butyl-4-methylpyridine is a sterically hindered, non-nucleophilic base which distinguishes between BrÖnsted (protonic) and Lewis acids. It also enables the direct high-yield conversion of aldehydes and ketones to vinyl triflates. It inhibits desilylation and hydration of the products during GaCl₃-catalyzed ortho-ethynylation of phenol.

Application

2,6-Di-tert-butyl-4-methylpyridine has been used:

• in the synthesis of 1,2-dihydro-2-silanaphthalene derivatives
• as base in PtCl₄-catalyzed cyclization reactions of homopropargyl azide derivatives
• diastereoselective synthesis of β-thiomannopyranosides

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302,H315,H319,H335
• Precautionary Statements: P261 - P264 - P270 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): 183.2 °F - closed cup
• Flash Point(C): 84 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves