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

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
2,6-Di-tert-butyl-4-methylpyridine Structure
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.)
Fp 183 °F
storage temp. 2-8°C
solubility ethanol: soluble5%, clear to slightly hazy, colorless to dark yellow
form Liquid or Low Melting Solid
pka6.88±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
InChIKeyHVHZEKKZMFRULH-UHFFFAOYSA-N
CAS DataBase Reference38222-83-2(CAS DataBase Reference)
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 Information
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ACROS English
SigmaAldrich English
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2,6-Di-tert-butyl-4-methylpyridine Usage And Synthesis
Chemical Propertieslight yellow powder
Uses2,6-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.
Uses2,6-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 Description2,6-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 MethodsA 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 materialsPivaloyl chloride-->Trifluoromethanesulfonic acid
Preparation ProductsMethyl isopropyl ether-->AcetaMide, 2,2,2-trifluoro-N-(2-iodophenyl)-
2,6-DITERT-BUTYLISONICOTINAMIDE 2,6-Di-tert-butyl-4-methylpyridine Cyhalofop-butyl tert-Butyl methyl ether tert-Butyldimethylsilyl chloride 4-Methylpyridine Buprofezin tert-Butanol Azamethiphos Diethylene glycol monobutyl ether Butyl acrylate Butyl acetate 2,6-Lutidine 2,6-DI-TERT-BUTYLPYRIDINE, POLYMER-BOUND 4-TERT-BUTYLPYRIDINE Di-tert-butyl peroxide DI-TERT-BUTYL ETHER 2-Butoxyethanol

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