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Methylpyridinium

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(Redirected from Methylpyridinium bromide)
Methylpyridinium
Names
Preferred IUPAC name 1-Methylpyridin-1-ium
Other names N-Methylpyridinium
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H8N/c1-7-5-3-2-4-6-7/h2-6H,1H3/q+1Key: PQBAWAQIRZIWIV-UHFFFAOYSA-N
  • InChI=1/C6H8N/c1-7-5-3-2-4-6-7/h2-6H,1H3/q+1Key: PQBAWAQIRZIWIV-UHFFFAOYAW
SMILES
  • 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 , 100 kPa). Infobox references
Chemical compound

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 an quaternary ammonium ion.

Preparation and occurrence

Methylpyridinium is prepared by treating pyridine with dimethylsulfate:

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

It is found in some coffee products. It is not present in unroasted coffee beans, but is formed during roasting from its precursor chemical, trigonelline. It is under investigation by scientists regarding its potential anti-carcinogenic properties, particularly an effect on colon cancer.

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).

See also

References

  1. Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2000). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. p. 558. doi:10.1002/14356007.a22_399. ISBN 9783527303854.
  2. E. A. Prill, S. M. McElvain (1935). "1-Methyl-2-Pyridone". Organic Syntheses. 15: 41. doi:10.15227/orgsyn.015.0041.
  3. ^ "Highly Active Compound Found In Coffee May Prevent Colon Cancer". ScienceDaily. Oct 15, 2003. Retrieved Oct 10, 2012.
  4. Boettler, U; Volz, N; Pahlke, G; Teller, N; Kotyczka, C; Somoza, V; Stiebitz, H; Bytof, G; et al. (2011). "Coffees rich in chlorogenic acid or N-methylpyridinium induce chemopreventive phase II-enzymes via the Nrf2/ARE pathway in vitro and in vivo". Molecular Nutrition & Food Research. 55 (5): 798–802. doi:10.1002/mnfr.201100115. PMID 21448860.
  5. Simonis, L.; Coppe, C.; Glibert, J.; Claes, P. (1986). "Properties of mixtures of zinc chloride and N-methylpyridinium chloride in the molten state – I. Phase diagram and heats of mixing". Thermochimica Acta. 99: 223–232. Bibcode:1986TcAc...99..223S. doi:10.1016/0040-6031(86)85285-6.
  6. Claes, P.; Simonis, L.; Glibert, J. (1986). "Properties of mixtures of zinc chloride and N-methylpyridinium chloride in the molten state – II. Specific mass, electrical conductivity and viscosity". Electrochimica Acta. 31 (12): 1525–1530. doi:10.1016/0013-4686(86)87071-2.
  7. Claes, P. F.; Coppe, C. R.; Simonis, L. A.; Glibert, J. E. (1987). "Properties of mixtures of zinc chloride and N-methylpyridinium chloride in the molten state – III. Solubility of hydrogen chloride under atmospheric pressure and comparison with zinc chloride—N-ethylpyridinium bromide mixtures". Journal of Chemical and Engineering Data. 32 (1): 70–72. doi:10.1021/je00047a020.
  8. Marković, R.; Minić, D. M. (1997). "Conductometric and thermal studies of fused Zn(II) salts containing methyl substituted pyridinium cations". Materials Chemistry and Physics. 50 (1): 20–24. doi:10.1016/S0254-0584(97)80178-2.
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