Aminal

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title: "Aminal" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["functional-groups"] description: "Type of organic compound or group" topic_path: "general/functional-groups" source: "https://en.wikipedia.org/wiki/Aminal" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Type of organic compound or group ::

::figure[src="https://upload.wikimedia.org/wikipedia/commons/0/04/Aminal-2D-skeletal.png" caption="Generic aminal"] ::

In organic chemistry, an aminal or aminoacetal is a functional group or type of organic compound that has two amine groups attached to the same carbon atom: . (As is customary in organic chemistry, R can represent hydrogen or an alkyl group). A common aminal is bis(dimethylamino)methane, a colorless liquid that is prepared by the reaction of dimethylamine and formaldehyde:{{cite journal |doi=10.15227/orgsyn.059.0153|title=Regioselective Mannich Condensation with Dimethyl(Methylene)ammonium Trifluoroacetate: 1-(Dimethylamino)-4-methyl-3-pentanone |first1=Michel|last1=Gaudry|first2=Yves|last2=Jasor|first3=Trung Bui |last3=Khac|journal=Org. Synth.|year=1979|volume=59|page=153}} :

Aminals are encountered in, for instance, the Fischer indole synthesis. Several examples exist in nature. Physostigmin.svg|Physostigmine, a highly toxic cholinesterase inhibitor found in the Calabar bean. Hodgkinsine.svg|Hodgkinsine, an alkaloid with antiviral, antibacterial and antifungal effects 5,10-methylenetetrahydrofolic acid.svg|5,10-Methylenetetrahydrofolate, an intermediate in one-carbon metabolism

Hexahydro-1,3,5-triazine (), an intermediate in the condensation of formaldehyde and ammonia, tends to degrade to hexamethylene tetraamine.

Cyclic aminals can be obtained by the condensation of a diamine and an aldehyde. Imidazolidines are one class of these cyclic aminals.

References

References

1. "aminals".
2. (1982). "Amino, Nitroso and Nitro Compounds and Their Derivatives: Vol. 2".
3. Hiersemann, M. "Functions bearing two nitrogens" in Comprehensive Organic Functional Group Transformations II 2005, volume 4, 411-441. Edited by Katritzky, Alan R.; Taylor, Richard J. K. {{doi. 10.1016/B0-08-044655-8/00075-1

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