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

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

Product Name:
2,6-Di-tert-butyl-4-methylpyridine
Synonyms:
  • Dibutylmethylpyridine
  • DTBMP
  • 2,6-DI-TERT-BUTYL-4-METHYLPYRIDINE
  • 4-Methyl-2,6-di-tert-butylpyridine
  • 2,6-Di-tert-butyl-4-methylpyridine,98%
  • 2,6-Bis(tert-butyl)-4-methylpyridine
  • 2,6-Di-tert-butyl-4-Methylpyridine, 98% 5GR
  • Pyridine, 2,6-bis(1,1-dimethylethyl)-4-methyl-
CAS:
38222-83-2
MF:
C14H23N
MW:
205.34
EINECS:
253-834-4
Product Categories:
  • Heterocycle-Pyridine series
  • C9 to C46
  • Pyridine series
  • Heterocyclic Building Blocks
  • Pyridines
  • Building Blocks
  • C13 to C40
  • Chemical Synthesis
  • Heterocyclic Building Blocks
  • 38222-83-2
Mol File:
38222-83-2.mol
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2,6-Di-tert-butyl-4-methylpyridine Chemical Properties

Melting point:
33-36 °C (lit.)
Boiling point:
233 °C (lit.)
Density 
1,476 g/cm3
refractive index 
n20/D 1.4763(lit.)
Flash point:
183 °F
storage temp. 
2-8°C
solubility 
ethanol: soluble5%, clear to slightly hazy, colorless to dark yellow
form 
Liquid or Low Melting Solid
pka
6.88±0.10(Predicted)
color 
brown
Water Solubility 
Sparingly soluble in water. Soluble in ethanol, acetic acid and diethyl ether.
Sensitive 
Air & Light Sensitive
BRN 
130503
InChIKey
HVHZEKKZMFRULH-UHFFFAOYSA-N
CAS DataBase Reference
38222-83-2(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38
Safety Statements 
26-37/39
WGK Germany 
3
8-10-23
HS Code 
29333990

MSDS

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2,6-Di-tert-butyl-4-methylpyridine Usage And Synthesis

Chemical Properties

light yellow powder

Uses

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.

Uses

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

Synthesis Reference(s)

The Journal of Organic Chemistry, 41, p. 3034, 1976 DOI: 10.1021/jo00880a027

General Description

2,6-Di-tert-butyl-4-methylpyridine is a sterically hindered, non-nucleophilic base which distinguishes between 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.

Purification Methods

A possible impurity is 2,6-di-tert-butyl-4-neopentylpyridine. Attempts to remove coloured impurities directly by distillation, acid-base extraction or treatment with activated charcoal were unsuccessful. Pure material is obtained by dissolving 0.3mole of the alkylpyridine in pentane (150mL) and introducing it at the top of a cold water jacketed chromatographic column (40 x 4.5cm) (cooling is necessary because the base in pentane reacts exothermically with alumina) containing activated and acidic alumina (300g). The column is eluted with pentane using a 1L constant pressure funnel fitted at the top of the column to provide slight pressure. All the pyridine is obtained in the first two litres of eluent (the progress of elution is monitored by spotting a fluorescent TLC plate and examining under short wave UV light—a dark blue spot is evidence for the presence of the alkylpyridine). Elution is complete in 1hour. Pentane is removed on a rotovap with 90-93% recovery yielding a liquid which solidifies on cooling, m 31-32o, and the base can be distilled. The HPtCl6 salt has m 213-314o(dec), and the CF3SO3H salt has m 202.5-203.5o (from CH2Cl2). [Anderson & Stang Org Synth Coll Vol VII 144 1981, Beilstein 20/6 V 190.]

2,6-Di-tert-butyl-4-methylpyridine Preparation Products And Raw materials

Raw materials

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