1-氨基乙醇

化合物

1-氨基乙醇(英语:1-Aminoethanol)是一种有机化合物,化学式为CH3CH(NH2)OH。它被归类为烷醇胺。具体来说,它是2-氨基乙醇结构异构体。这两种化合物的氨基位置不同。由于1-氨基乙醇的中心碳原子有四个不同的取代基,因此该化合物有两种立体异构体。与在商业中相当重要的2-氨基乙醇不同,1-氨基乙醇不会作为纯物质出现,主要具有理论意义。

1-氨基乙醇
IUPAC名
1-Aminoethan-1-ol
1-氨基乙-1-醇
别名 1-氨基乙醇
乙醛合氨
识别
CAS号 75-39-8  checkY
PubChem 522583
ChemSpider 455852
SMILES
 
  • CC(N)O
InChI
 
  • 1S/C2H7NO/c1-2(3)4/h2,4H,3H2,1H3
InChIKey UJPKMTDFFUTLGM-UHFFFAOYSA-N
EINECS 200-868-2
性质
化学式 C2H7NO
摩尔质量 61.08 g·mol−1
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

1-氨基乙醇存在于乙醛氨水的溶液中。[1]

1-氨基乙醇被认为是丙氨酸合成的斯特雷克反应的中间体。[2]

历史

1-氨基乙醇于1833年由德国化学家约翰·沃尔夫冈·德贝莱纳首先制备;其最简式最早由德国化学家尤斯图斯·冯·李比希于1835年确定。[3]1-氨基乙醇的结构直到1877年仍未得到证实,当时德裔意大利化学家罗伯特·希夫证明其结构为 CH3CH(OH)NH2[4]

参考资料

  1. ^ Smith, Michael B.; March, Jerry, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure 6th, New York: Wiley-Interscience, 2007, ISBN 978-0-471-72091-1 
  2. ^ Shinichi Yamabe; Guixiang Zeng; Wei Guan; Shigeyoshi Sakaki. Proton transfers in the Strecker reaction revealed by DFT calculations. Beilstein Journal of Organic Chemistry. 2014, 10: 1765–1774 [2023-03-07]. PMC 4143099 . PMID 25161735. doi:10.3762/bjoc.10.184. (原始内容存档于2016-08-22). 
  3. ^ Liebig, Justus (1835) "Ueber die Producte der Oxydation des Alkohols"页面存档备份,存于互联网档案馆) (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: