2,6-Di-tert-butyl-4-methylpyridine CAS NO.38222-83-2

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
Mol File:    38222-83-2.mol

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
pka    6.88±0.10(Predicted)
form     Liquid or Low Melting Solid
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)
Safety Information
Hazard Codes     Xn,Xi
Risk Statements     22-36/37/38
Safety Statements     26-37/39
WGK Germany     3
F     8-10-23
HS Code     29333990
MSDS Information
Provider    Language
ACROS    English
SigmaAldrich    English
ALFA    English
2,6-Di-tert-butyl-4-methylpyridine Usage And Synthesis
Chemical Properties    light yellow powder
Synthesis Reference(s)    The Journal of Organic Chemistry, 41, p. 3034, 1976 DOI: 10.1021/jo00880a027
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    Pivaloyl chloride-->Trifluoromethanesulfonic acid
Preparation Products    Methyl isopropyl ether