1-Aminoethanol

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1-Aminoethanol
1-Aminoethanol.png
Names
Preferred IUPAC name
1-Aminoethan-1-ol
Other names
1-Aminoethanol
Acetaldehyde ammonia
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.790
Properties
C2H7NO
Molar mass 61.08 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1-Aminoethanol is the organic compound with the formula CH3CH(NH2)OH. It is classified as an alkanolamine. 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 substitutents, the compound has two stereoisomers. 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]

1-Aminoethanol is suggested as intermediate in Strecker reaction of alanine synthesis.[2]

1-Aminoethanol was first prepared in 1833 by the German chemist Johann Wolfgang Döbereiner; its empirical formula was first determined by the German chemist Justus von Liebig in 1835.[3] The structure of 1-aminoethanol remained unproven until 1877, when the German-Italian chemist Robert Schiff showed that the structure was CH3CH(OH)NH2.[4]

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. ^ Shinichi Yamabe; Guixiang Zeng; Wei Guan; Shigeyoshi Sakaki (2014). "Proton transfers in the Strecker reaction revealed by DFT calculations". Beilstein Journal of Organic Chemistry. doi:10.3762/bjoc.10.184. 
  3. ^ Liebig, Justus (1835) "Ueber die Producte der Oxydation des Alkohols" (On the products of oxidation of alcohol [i.e., ethanol]), Annalen der Chemie, 14 : 133–167. In 1821, Döbereiner had prepared what he called Saüerstoffäther (literally: ether oxide), which, as Liebig later showed, contained acetaldehyde, on p. 134, Liebig states that Döbereiner first produced 1-amino-ethanol by perfusing acetaldehyde (Saüerstoffäther or Aldehyd, as Liebig called it) with ammonia gas (Ammoniak) : "Der berühmte Entdecker des Acetals theilte mir damals gleichzeitig mit, dass sein Saüerstoffäther mit Ammoniakgas eine weisse krystallinische Verbingdung bilde; … " (The famous discoverer of acetal [viz, Döbereiner] simultaneously communicated to me at that time that his ether oxide forms a white crystalline compound with ammonia gas; … ) On p. 146, Liebig presented his empirical formula for 1-aminoethanol: C4H14N2O2. If the subscripts are divided by 2, the resulting formula is correct.
  4. ^ Although it had long been assumed that the structure of 1-aminoethanol was CH3CH(OH)NH2, it had not been proven that 1-aminoethanol contained a hydroxyl (-OH) group until Schiff's investigation in 1877. See: