1-Aminoethanol

2-aminoethanol 1-Aminoethanol.png 120px skin-invert 1_aminoethanol.png bg-transparent 1-Aminoethan-1-ol 1-AminoethanolAcetaldehyde ammonia 455852 522583 1S/C2H7NO/c1-2(3)4/h2,4H,3H2,1H3 UJPKMTDFFUTLGM-UHFFFAOYSA-N CC(N)O 75-39-8 correct CAS correct FDA 4J67Y8SM0K 200-868-2 2 1 1 7 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-Aminoethanol is suggested as intermediate in Strecker reaction of alanine synthesis.Proton transfers in the Strecker reaction revealed by DFT calculations Shinichi Yamabe Guixiang Zeng Wei Guan Shigeyoshi Sakaki Beilstein Journal of Organic Chemistry http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-10-184 10.3762/bjoc.10.184 2014 10 1765–1774 25161735 4143099 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.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. The structure of 1-aminoethanol remained unproven until 1877, when the German-Italian chemist Robert Schiff showed that the structure was CH3CH(OH)NH2.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. References Category:Primary alcohols Category:Amines Category:Substances discovered in the 19th century Category:Amino alcohols Category:Organic compounds with 2 carbon atoms