1-氨基乙醇

化合物

1-氨基乙醇(英語:1-Aminoethanol)是一種有機化合物,化學式為CH3CH(NH2)OH。它被歸類為烷醇胺。具體來說,它是2-氨基乙醇結構異構體。這兩種化合物的氨基位置不同。由於1-氨基乙醇的中心碳原子有四個不同的取代基,因此該化合物有兩種立體異構體。與在商業中相當重要的2-氨基乙醇不同,1-氨基乙醇不會作為純物質出現,主要具有理論意義。

1-氨基乙醇
IUPAC名
1-Aminoethan-1-ol
1-氨基乙-1-醇
別名 1-氨基乙醇
乙醛合氨
識別
CAS編號 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
性質
化學式 C2H7NO
摩爾質量 61.08 g·mol−1
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

1-氨基乙醇存在於乙醛氨水的溶液中。[1]

1-氨基乙醇被認為是丙氨酸合成的斯特雷克反應的中間體。[2]

歷史

1-氨基乙醇於1833年由德國化學家約翰·沃爾夫岡·德貝萊納首先製備;其最簡式最早由德國化學家尤斯圖斯·馮·李比希於1835年確定。[3]1-氨基乙醇的結構直到1877年仍未得到證實,當時德裔意大利化學家羅伯特·希夫證明其結構為 CH3CH(OH)NH2[4]

參考資料

  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. (原始內容存檔於2016-08-22). 
  3. ^ Liebig, Justus (1835) "Ueber die Producte der Oxydation des Alkohols"頁面存檔備份,存於互聯網檔案館) (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: