3-hydroxypyridine
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| General | ||||||||||||||||
| Surname | 3-hydroxypyridine | |||||||||||||||
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| Molecular formula | C 5 H 5 NO | |||||||||||||||
| Brief description |
colorless solid |
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| properties | ||||||||||||||||
| Molar mass | 95.10 g mol −1 | |||||||||||||||
| Physical state |
firmly |
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| Melting point |
129 ° C |
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| solubility |
moderate in water (33 g l −1 at 20 ° C) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
3-Hydroxypyridine is an organic compound with the empirical formula C 5 H 5 NO. It is isomeric to 2-pyridone and 4-pyridone , but has fundamentally different properties and reactivity.
presentation
The synthesis of 3-hydroxypyridine proceeds by reaction of furfural with ammonia . In addition, it can be obtained by reacting 3-bromopyridine under pressure in an alkali melt .
properties
In terms of its properties, 3-hydroxypyridine differs fundamentally from its isomers 2- and 4-pyridone, since it cannot form a keto form. In contrast, 3-hydroxypyridine has a zwitterionic boundary structure , the proportion of which in the chemical equilibrium depends on the solvent . Thus 3-hydroxypyridine reacts similarly to phenol and not similarly to amide . It is preferred the nitrogen protonated having a pK s value has of 5.2.
Occurrence and use
3-Hydroxypyridine is produced in low concentrations during the Maillard reaction . It can also be found as a pyridoxine structural element in vitamin B 6, for example .
It can be used to make insecticides and herbicides . It can also be used for the synthesis of certain cholinesterase inhibitors , for example pyridostigmine . It can also be reduced to 3-hydroxypiperidine .
Structural formula of pyridoxine
Structural formula of pyridostigmine
Individual evidence
- ↑ a b c d Entry on pyridinols. In: Römpp Online . Georg Thieme Verlag, accessed on September 29, 2014.
- ↑ a b c Data sheet 3-Pyridinol (PDF) from Merck , accessed on March 18, 2011.
- ↑ JA Joules, K. Mills: Heterocyclic Chemistry 2000, 4th Edition, Blackwell Science, Oxford, pp. 88-91; ISBN 0-632-05453-0 .
- ↑ Sh. Topova, D. Bojilov, S. Dagnon, O. Argirov: Hydroxypyridine Formation In Model System Monosodium Glutamate And 2-Fufural . In: Applied Science Reports . tape 2 , no. 2 , 2014, p. 71-77 , doi : 10.15192 / PSCP.ASR.2014.2.2.7177 .