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
CAS Number	461-98-3;
3D model (JSmol)	Interactive image;
ChemSpider	61354;
ECHA InfoCard	100.006.656
EC Number	207-320-1;
PubChem CID	68039;
CompTox Dashboard (EPA)	DTXSID50196725 ;
	InChI InChI=1S/C6H9N3/c1-4-3-6(7)9-5(2)8-4/h3H,1-2H3,(H2,7,8,9) Key: BJJDXAFKCKSLTE-UHFFFAOYSA-N;
	SMILES CC1=CC(=NC(=N1)C)N;
Properties
Chemical formula	C6H9N3
Molar mass	123.159 g·mol−1
Appearance	crystalline solid
Odor	irritating
Melting point	180–185 °C (356–365 °F; 453–458 K)
Solubility in water	soluble
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

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.^[2]

Properties

Cyanomethine is a strongly basic^[4] colourless to white crystalline solid. It is soluble in water and slightly soluble in alcohol.^[1]

Cyanomethine can form complexes with platinum(II) and platinum(IV) compounds.^[5]

Synthesis

Cyanomethine is prepared by the trimerisation of acetonitrile with sodium or potassium,^[6] with the corresponding metal cyanide and C₄H₆N₂ (possibly 2-methylimidazole or 3-methylpyrazole; iminoacetonitrile has been identified^[7]) as the main byproducts.^[8] It can also made by reaction of sodium methoxide and acetonitrile.^[2]

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.^[9]

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

References

^ ^a ^b ^c Roscoe, H. E. (1881). A Treatise on chemistry volume 3, 1881.page 523-524
^ ^a ^b ^c ^d Polymerisation of Nitriles, Journal of the Chemical Society. (1890). United Kingdom: Chemical Society.page 1158
^ "4-Amino-2,6-dimethylpyrimidine". pubchem.ncbi.nlm.nih.gov.
^ Karrer, P. (1950). Organic Chemistry. page 819
^ 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
^ Miller, W. A., McLeod, H. (1880). Elements of Chemistry: Theoretical and Practical, page 174
^ Derivatives of Hydrocyanic Acid. Competition Science Vision. Jan 2001 page 1494
^ Methyl cyanide, Thorpe, T. E. (1895). A Dictionary of Applied Chemistry. United Kingdom: Longmans. page 575
^ 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 [1]

[roscoe-1] Roscoe, H. E. (1881). A Treatise on chemistry volume 3, 1881.page 523-524

[nitriles-2] 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

[miller-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 [1]

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