1-Aminoethanol is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula CHCH(NH)OH. It is classified as an
alkanolamine
In organic chemistry, alkanolamines are organic compounds that contain both hydroxyl () and amino (, , and ) functional groups on an alkane backbone. The term alkanolamine is a broad class term that is sometimes used as a subclassification.
Meth ...
. Specifically, it is 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 substituents, the compound has two
stereoisomers
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...
. Unlike 2-aminoethanol, which is of considerable importance in commerce, 1-aminoethanol is not encountered as a pure material and is mainly of theoretical interest.
1-Aminoethanol exists in a solution of acetaldehyde and aqueous ammonia.
1-Aminoethanol is suggested as intermediate in
Strecker reaction
The Strecker amino acid synthesis, also known simply as the Strecker synthesis, is a method for the synthesis of amino acids by the reaction of an aldehyde with ammonia in the presence of potassium cyanide. The condensation reaction yields an α- ...
of
alanine
Alanine (symbol Ala or A), or α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the central carbon atom which also carries a methyl group side c ...
synthesis.
1-Aminoethanol was first prepared in 1833 by the German chemist
Johann Wolfgang Döbereiner
Johann Wolfgang Döbereiner (13 December 1780 – 24 March 1849) was a German chemist who is best known for work that foreshadowed the periodic law for the chemical elements, and for inventing the first lighter, which was known as the Döberei ...
; its empirical formula was first determined by the German chemist
Justus von Liebig
Justus Freiherr von Liebig (12 May 1803 – 20 April 1873) was a German scientist who made major contributions to agricultural and biological chemistry, and is considered one of the principal founders of organic chemistry. As a professor at t ...
in 1835. The structure of 1-aminoethanol remained unproven until 1877, when the German-Italian chemist
Robert Schiff
Robert Schiff (July 25, 1854 in Frankfurt am Main, Germany – 1940 in Massa, Tuscany, Massa, Italy) was a German-born, Italian chemist.
He was the son of physiologist Moritz Schiff and Claudia Trier. He successively was a student at the Unive ...
showed that the structure was CHCH(OH)NH.
[Although it had long been assumed that the structure of 1-aminoethanol was CHCH(OH)NH, it had not been proven that 1-aminoethanol contained a hydroxyl (-OH) group until Schiff's investigation in 1877. See:
* Schiff, Robert (1877]
"Zur Constitution des Chloralammoniaks und des Aldehydammoniaks,"
''Berichte der Deutschen Chemischen Gesellschaft'', 10 : 165–171.
* Aschan, Ossian (1915
"Neues über Aldehyd-ammoniak und Chloral-ammoniak."
''Berichte der Deutschen Chemischen Gesellschaft'', 48 (1) : 874–891.
References
{{DEFAULTSORT:Aminoethanol, 1-
Primary alcohols
Amines