Kyanäthin
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| General | ||||||||||
| Surname | Kyanäthin | |||||||||
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| Molecular formula | C 9 H 15 N 3 | |||||||||
| Brief description |
white, odorless and almost tasteless |
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| properties | ||||||||||
| Molar mass | 165.24 g mol −1 | |||||||||
| Melting point |
~ 190 ° C |
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| boiling point |
280 ° C (partly decomp.) |
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| solubility |
soluble in ethanol; Very little soluble in cold water, more easily soluble in boiling water |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||
The old name kyanäthin (also cyanäthin ) stands for 4-amino-2,6-diethyl-5-methyl pyrimidine . It is the first synthetically produced heterocyclic compound .
It was first produced in 1848 by Hermann Kolbe and Edward Frankland in the laboratory of Robert Bunsen through the action of propionitrile (old name: cyanoethyl ) on elemental potassium . At first the wrong formula C 18 H 15 N 3 was assigned to the kyanethine . The investigations at that time were part of the studies on radical theory , so they contributed to the development of organic structural chemistry . The discovery of kyanäthin coincided with that of diethylzinc . Both discoveries are based on the same idea: the reaction of an alkyl halide or an alkyl pseudohalide with a base metal. The reaction of propionitrile and potassium mainly yields ethane and n- butane , 4-amino-2,6-diethyl-5-methylpyrimidine is only formed in small amounts. It may be due to this fact that the structure was largely ignored.
The trimerization of nitriles to pyrimidines is still part of research today, but is now carried out in far better yields with alkoxide bases.
Individual evidence
- ↑ a b c d e F. Frankland, H. Kolbe: "Ueber die Zersetzungproducte des Cyanäthyls durch Kalium", in: Pharmaceutisches Centralblatt , No. 24, May 31, 1848, pp. 369-375 ( full text in the Google book search ).
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ E. von Meyer: "About Kyanäthin and new bases emerging from it", in: Journal für Praktische Chemie , 1880 , 22 , pp. 261-288; doi : 10.1002 / prac.18800220118 .
- ^ Ian R. Baxendale, Steven V. Ley: "Formation of 4-aminopyrimidines via the Trimerization of Nitriles Using Focused Microwave Heating", in: J Comb Chem . , 2005 , 7 (3), pp. 483-489; doi : 10.1021 / cc049826d .