Alkanolamine

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Alkanolamines are chemical compounds that contain both hydroxy (-OH) and amino (-NH2, -NHR, and -NR2) functional groups on an alkane backbone. The term alkanolamine is a broad class term that is sometimes used as a subclassification.[1]

2-Aminoalcohols[edit]

Chemical structure of ethanolamine, a simple amino alcohol.

2-Aminoalcohols are an important class of organic compounds that contain both an amine and an alcohol functional groups. They are generated often by the reaction of amines with epoxides. Such compounds find a variety of industrial applications. Simple alkanolamines are used as solvents, synthetic intermediates, and high-boiling bases.[2]

Common amino alcohols

Beta blockers[edit]

A subclass of beta blockers is often called alkanolamine beta blockers. Typical examples are:

1-Aminoalcohols[edit]

1-Aminoalcohols are rarely encountered as pure materials but are important intermediates in both the conversion of aldehydes to imines and the reverse reaction, the hydrolysis of imines.

One example is 1-aminoethanol (CH3CH(NH2)(OH)), a structural isomer of 2-aminoethanol (ethanolamine). These two compounds differ in the position of the amino group. Since the central carbon atom in 1-aminoethanol has four different substitutents, the compound has two stereoisomers, L-aminoethanol and R-aminoethanol. It is known as alanaminol because it has the same side chain as alanine. 1-Aminoethanol converts to acetaldehyde and ammonia.

Natural products[edit]

Amino alcohol analogues of alpha-amino acidss and related compounds[edit]

Most proteins and peptides contain both alcohols and amino groups. Two amino acids are alkanolamines, formally speaking: serine and hydroxyproline. In principle each amino acid can be hydrogenated to the corresponding 2-aminoalcohol. The names of these derivatives are listed below:


See also[edit]

References[edit]

  1. ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 0-471-72091-7 
  2. ^ Matthias Frauenkron, Johann-Peter Melder, Günther Ruider, Roland Rossbacher, Hartmut Höke “Ethanolamines and Propanolamines” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_001

External links[edit]