Methylpyridinium

Methylpyridinium is an ion with the formula C₅H₅NCH+3. It is the N-methylated derivative of pyridine. It confers no color to its salts. The ion is classified as a quaternary ammonium ion.^[1]

Methylpyridinium

Names
Preferred IUPAC name 1-Methylpyridin-1-ium
Other names N-Methylpyridinium
Identifiers
CAS Number	694-56-4 Y
3D model (JSmol)	Interactive image
ChemSpider	13008
PubChem CID	13597
CompTox Dashboard (EPA)	DTXSID70989212
InChI InChI=1S/C6H8N/c1-7-5-3-2-4-6-7/h2-6H,1H3/q+1 Key: PQBAWAQIRZIWIV-UHFFFAOYSA-N InChI=1/C6H8N/c1-7-5-3-2-4-6-7/h2-6H,1H3/q+1 Key: PQBAWAQIRZIWIV-UHFFFAOYAW
SMILES [n+]1(ccccc1)C
Properties
Chemical formula	C6H8N+
Molar mass	94.134 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Preparation and occurrence

Methylpyridinium is prepared by treating pyridine with dimethylsulfate:^[2]

C₅H₅N + (CH₃O)₂SO₂ → [C₅H₅NCH₃]⁺CH₃OSO−3

It is found in some coffee products.^[3] It is not present in unroasted coffee beans, but is formed during roasting from its precursor chemical, trigonelline.^[3]

Ionic liquid

The chloride salt of N-methylpyridinium behaves as an ionic liquid. Mixtures of that salt and zinc chloride have been characterised over the temperature range 150–200 °C (423–473 K).^[4][5][6][7]

See also

• Pyridinium
• 4-Caffeoyl-1,5-quinide
• Coffee portal