1-氨基乙醇

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
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（英語：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-氨基乙醇的结构异构体。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-氨基乙醇存在于乙醛和氨水的溶液中。^[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

^ Smith, Michael B.; March, Jerry, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure 6th, New York: Wiley-Interscience, 2007, ISBN 978-0-471-72091-1
^ 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）.
^ 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.
^
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," （页面存档备份，存于互联网档案馆） Berichte der Deutschen Chemischen Gesellschaft, 10 : 165–171.
- Aschan, Ossian (1915) "Neues über Aldehyd-ammoniak und Chloral-ammoniak." （页面存档备份，存于互联网档案馆） Berichte der Deutschen Chemischen Gesellschaft, 48 (1) : 874–891.

[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:
Schiff, Robert (1877) "Zur Constitution des Chloralammoniaks und des Aldehydammoniaks," （页面存档备份，存于互联网档案馆） Berichte der Deutschen Chemischen Gesellschaft, 10 : 165–171.

Aschan, Ossian (1915) "Neues über Aldehyd-ammoniak und Chloral-ammoniak." （页面存档备份，存于互联网档案馆） Berichte der Deutschen Chemischen Gesellschaft, 48 (1) : 874–891.

[5] Schiff, Robert (1877) "Zur Constitution des Chloralammoniaks und des Aldehydammoniaks," （页面存档备份，存于互联网档案馆） Berichte der Deutschen Chemischen Gesellschaft, 10 : 165–171.

[6] Aschan, Ossian (1915) "Neues über Aldehyd-ammoniak und Chloral-ammoniak." （页面存档备份，存于互联网档案馆） Berichte der Deutschen Chemischen Gesellschaft, 48 (1) : 874–891.

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