1-Aminoethanol

Not to be confused with 2-aminoethanol.

1-Aminoethanol

Names
Preferred IUPAC name 1-Aminoethan-1-ol
Other names 1-Aminoethanol Acetaldehyde ammonia
Identifiers
CAS Number	75-39-8  Y
3D model (JSmol)	Interactive image
ChemSpider	455852
ECHA InfoCard	100.000.790
EC Number	200-868-2
PubChem CID	522583
UNII	4J67Y8SM0K  Y
CompTox Dashboard (EPA)	DTXSID60996495
InChI InChI=1S/C2H7NO/c1-2(3)4/h2,4H,3H2,1H3 Key: UJPKMTDFFUTLGM-UHFFFAOYSA-N
SMILES CC(N)O
Properties
Chemical formula	C2H7NO
Molar mass	61.084 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 an 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 substituents, 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

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. Shinichi Yamabe; Guixiang Zeng; Wei Guan; Shigeyoshi Sakaki (2014). "Proton transfers in the Strecker reaction revealed by DFT calculations". Beilstein Journal of Organic Chemistry . 10: 1765–1774. doi:10.3762/bjoc.10.184. PMC   4143099 . PMID   25161735.
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:
   • 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.