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

Bezeichnung:2,6-Di-tert-butyl-4-methylpyridin

CAS-Nr38222-83-2

Englisch Name:2,6-Di-tert-butyl-4-methylpyridine

CBNumberCB1165928

SummenformelC14H23N

Molgewicht205.34

MOL-Datei38222-83-2.mol

Synonyma

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

2,6-Di-tert-butyl-4-methylpyridin physikalisch-chemischer Eigenschaften

Schmelzpunkt	33-36 °C (lit.)
Siedepunkt	233 °C (lit.)
Dichte	1,476 g/cm³
Brechungsindex	n20/D 1.4763(lit.)
Flammpunkt	183 °F
storage temp.	2-8°C
Löslichkeit	ethanol: soluble5%, clear to slightly hazy, colorless to dark yellow
Aggregatzustand	Liquid or Low Melting Solid
pka	6.88±0.10(Predicted)
Farbe	brown
Wasserlöslichkeit	Sparingly soluble in water. Soluble in ethanol, acetic acid and diethyl ether.
Sensitive	Air & Light Sensitive
BRN	130503
InChIKey	HVHZEKKZMFRULH-UHFFFAOYSA-N
CAS Datenbank	38222-83-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	22-36/37/38
S-Sätze:	26-37/39
WGK Germany	3
F	8-10-23
HS Code	29333990

Gefahreninformationscode (GHS)

2,6-Di-tert-butyl-4-methylpyridine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
light yellow powder
Verwenden
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
Verwenden
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.
Synthesis Reference(s)
The Journal of Organic Chemistry, 41, p. 3034, 1976 DOI: 10.1021/jo00880a027
Allgemeine Beschreibung
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.
läuterung methode
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 Upstream-Materialien And Downstream Produkte

2,6-Di-tert-butyl-4-methylpyridin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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