Alkanolamine

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Alkanolamines are chemical compounds that carry 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.[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 not commonly 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 exists in a solution of acetaldehyde and ammonia.

Simple[edit]

Simple alkanolamines are used as solvents, chemical precursors, and high-boiling bases:

Alkaloids[edit]

Other[edit]

The co-existence of hydroxy and amine groups in one molecule is very common in medications and biochemicals, examples are:

There are amino alcohol analogues of each of the amino acids, all of which can react with formic acid to make the corresponding amino acid. (For example, Glycaminol + formic acid --> Glycine + water)

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 M elder, Günther Ruider, Roland Rossbacher, Hartmut Höke “Ethanolamines and Propanolamines” in Ullmann's Encyclopedia of Industrial Chemistry 2002 by Wiley-VCH, Weinheim doi:10.1002/14356007.a10_001

External links[edit]