2,4,6-Trimethylpyridin

Bezeichnung:2,4,6-Trimethylpyridin

CAS-Nr108-75-8

Englisch Name:2,4,6-Collidine

CBNumberCB6852760

SummenformelC8H11N

Molgewicht121.18

MOL-Datei108-75-8.mol

Synonyma

2,4,6-Trimethylpyridin

2,4,6-Trimethylpyridin physikalisch-chemischer Eigenschaften

Schmelzpunkt	-43 °C (lit.)
Siedepunkt	171-172 °C (lit.)
Dichte	0.917 g/mL at 25 °C (lit.)
Dampfdruck	4 hPa (20 °C)
Brechungsindex	n20/D 1.498(lit.)
Flammpunkt	135 °F
storage temp.	Store below +30°C.
Löslichkeit	35g/l
pka	7.43(at 25℃)
Aggregatzustand	Liquid
Farbe	Clear colorless to yellow
Wasserlöslichkeit	35 g/L (20 ºC)
Sensitive	Hygroscopic
Merck	14,9718
BRN	107283
Dielectric constant	1.9（20℃）
Stabilität	Stable. Combustible. Incompatible with strong oxidizing agents.
LogP	1.25 at 20℃
CAS Datenbank	108-75-8(CAS DataBase Reference)
NIST chemische Informationen	Pyridine, 2,4,6-trimethyl-(108-75-8)
EPA chemische Informationen	2,4,6-Trimethylpyridine (108-75-8)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	10-20/21/22-36/37/38
S-Sätze:	26-36/37-36
RIDADR	UN 1992 3/PG 3
WGK Germany	3
RTECS-Nr.	UU0970000
TSCA	Yes
HazardClass	3
PackingGroup	III
HS Code	29333999
Giftige Stoffe Daten	108-75-8(Hazardous Substances Data)
Toxizität	LD50 orally in Rabbit: 400 mg/kg

Gefahreninformationscode (GHS)

2,4,6-Collidine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R10:Entzündlich.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
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.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
colourless liquid
Verwenden
2,4,6-Collidine is used as a tissue fixative for electron microscopy. It is useful in dehydrohalogenation reactions and acts as a solvent for the cleavage of hindered esters by anhydrous lithium iodide.
Verwenden
2,4,6-Collidine is an reagent used for various synthetic preparations such as the synthesis of methylated pyridines by three-componet catalytic condensation of acetylene, acetone and ammonia.
Definition
Methyl, ethyl, propyl, and trimethyl homologs of pyridine.
Synthesis Reference(s)
Journal of the American Chemical Society, 72, p. 4184, 1950 DOI: 10.1021/ja01165a097
Allgemeine Beschreibung
2,4,6-Trimethylpyridine is a pyridine derivative. It has a pK of 7.4. The product can react with trifluoroiodomethane in cyclopentane solution to afford 1:1 complex. This complex was investigated by NMR (Nuclear Magnetic Resonance) spectroscopy. Collidine-buffered osmium tetroxide solutions have been prepared by adding osmium tetroxide solution to it. These solutions have been used as fixative for electron microscopic studies.
2,4,6-Trimethylpyridine can undergo oxidation with potassium permanganate to form 2,4,6-pyridinetricarboxylic acid.
Hazard
Toxic.
Flammability and Explosibility
Flammable
läuterung methode
Commercial samples may be grossly impure. Likely contaminants include 3,5-dimethylpyridine, 2,3,6-trimethylpyridine and water. Brown, Johnson and Podall [J Am Chem Soc 76 5556 1954] fractionally distilled 2,4,6-trimethylpyridine under reduced pressure through a 40cm Vigreux column (p 11) and added to 430mL of the distillate slowly, with cooling to 0o, 45g of BF3-diethyl etherate. The mixture was again distilled, and an equal volume of dry *benzene was added to the distillate. Dry HCl was passed into the solution, which was kept cold in an ice-bath, and the hydrochloride was filtered off. It was recrystallised from absolute EtOH (1.5mL/g) to m 286-287o[m 256o(sealed tube), also m 293-294o subliming slowly]. The free base was regenerated by treatment with aqueous NaOH, then extracted with *benzene, dried (MgSO4) and distilled under reduced pressure. Sisler et al. [J Am Chem Soc 75 446 1953] precipitated trimethylpyridine as its phosphate from a solution of the base in MeOH by adding 85% H3PO4, shaking and cooling. The free base was regenerated as above. Garrett and Smythe [J Chem Soc 763 1903] purified the trimethylpyridine via the HgCl2 complex. It is more soluble in cold than hot H2O [the solubility is 20.8% at 6o, 3.5% at 20o, 1.8% at 100o]. Alternatively, purify it by dissolving it in CHCl3, adding solid K2CO3 and Drierite, filtering and fractionally distilling through an 8in helix-packed column. The sulfate has m 205o, and the picrate (from hot H2O) has m 155-156o. [Frank & Meikle J Am Chem Soc 72 4184 1950, Beilstein 20 H 250, 20 I 87, 20 II 164, 20 III/IV 2810, 20/6 V 93.]

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