1-Amino-1-propanol

Alkanolamines are chemical compounds that contain both hydroxyl (-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]

1-Aminoalcohols[]

1-Aminoalcohols are better known as hemiaminals. Methanolamine is the simplest member.

2-Aminoalcohols[]

Key members: ethanolamine, dimethylethanolamine, N-methylethanolamine, Aminomethyl propanol

Two popular drugs, often called alkanolamine beta blockers, are members of this structural class: propranolol, pindolol. Isoetarine is yet another medicinally useful derivative of ethanolamine.

2-Aminoalcohols are an important class of organic compounds that are often generated often by the reaction of amines with epoxides. Simple alkanolamines are used as solvents, synthetic intermediates, and high-boiling bases.[2]

Preparation[]

Ethylene oxide and related epoxides add to amines:[2]

C2H4O + R−NH2 → RNHC2H4OH

Hydrogenation of amino acids gives the corresponding 2-aminoalcohols. Examples include prolinol (from proline) and valinol (from valine).

1,3-, 1,4-, and 1,5-amino alcohols[]

Natural products[]

Most proteins and peptides contain both alcohols and amino groups. Two amino acids are alkanolamines, formally speaking: serine and hydroxyproline.

References[]

  1. ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 978-0-471-72091-1
  2. ^ a b Matthias Frauenkron; Johann-Peter Melder; Günther Ruider; Roland Rossbacher; Hartmut Höke (2002). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001. ISBN 3527306730.

External links[]