Cyanomethine

Cyanomethine
Names
IUPAC name
4-Amino-2,6-dimethylpyrimidine
Other names
  • Cyanmethine
  • Kyanmethin
  • 6-Amino-2,4-dimethylpyrimidine
  • 2,6-Dimethyl-4-pyrimidinamine
  • 2,6-Dimethylpyrimidin-4-ylamine
  • Trimethyl cyanuride
  • Amidodimethylmetadiazine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.656 Edit this at Wikidata
EC Number
  • 207-320-1
UNII
  • InChI=1S/C6H9N3/c1-4-3-6(7)9-5(2)8-4/h3H,1-2H3,(H2,7,8,9)
    Key: BJJDXAFKCKSLTE-UHFFFAOYSA-N
  • CC1=CC(=NC(=N1)C)N
Properties
C6H9N3
Molar mass 123.159 g·mol−1
Appearance crystalline solid
Odor irritating
Melting point 180–185 °C (356–365 °F; 453–458 K)
soluble
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyanomethine (4-amino-2,6-dimethylpyrimidine) is an amino and methylated derivative of pyrimidine with the chemical formula C6H9N3, belonging to a class named cyanalkines.

Properties

Cyanomethine is a strongly basic colourless to white crystalline solid. It is soluble in water and slightly soluble in alcohol.

Cyanomethine can form complexes with platinum(II) and platinum(IV) compounds.

Synthesis

Cyanomethine is prepared by the trimerisation of acetonitrile with sodium or potassium, with the corresponding metal cyanide and C4H6N2 (possibly 2-methylimidazole or 3-methylpyrazole; iminoacetonitrile has been identified) as the main byproducts. It can also made by reaction of sodium methoxide and acetonitrile.

The correspondence of the three acetonitrile units to a tautomer of cyanomethine is:

At higher pressure, sodium methoxide instead catalyzes trimerization to form 2,4,6-Trimethyl-1,3,5-triazine.

2,6-Diethyl-5-methyl-4-pyrimidinamine (cyan(o)ethine) is an analogous structure that can be made by trimerization of propionitrile.

References

  1. 1 2 3 Roscoe, H. E. (1881). A Treatise on chemistry volume 3, 1881.page 523-524
  2. 1 2 3 4 Polymerisation of Nitriles, Journal of the Chemical Society. (1890). United Kingdom: Chemical Society.page 1158
  3. ↑ "4-Amino-2,6-dimethylpyrimidine". pubchem.ncbi.nlm.nih.gov.
  4. ↑ Karrer, P. (1950). Organic Chemistry. page 819
  5. ↑ Kovala-Demertzi, D. Platinum(II) and platinum(IV) complexes of 2-amino-4,6-dimethylpyrimidine. Transition Met Chem 15, 23–26 (1990). https://doi.org/10.1007/BF01032225
  6. ↑ Miller, W. A., McLeod, H. (1880). Elements of Chemistry: Theoretical and Practical, page 174
  7. ↑ Derivatives of Hydrocyanic Acid. Competition Science Vision. Jan 2001 page 1494
  8. ↑ Methyl cyanide, Thorpe, T. E. (1895). A Dictionary of Applied Chemistry. United Kingdom: Longmans. page 575
  9. ↑ T. L. Cairns, A. W. Larchar, and B. C. McKusick, The Trimerization of Nitriles at High Pressures, J. Am. Chem. Soc. 1952, 74, 22, 5633–5636 Publication Date: November 1, 1952