1-アミノエタノール

1-アミノエタノール
物質名
	優先IUPAC名 1-Aminoethan-1-ol
	別名 1-Aminoethanol; Acetaldehyde ammonia
識別情報
CAS登録番号	75-39-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	455852;
ECHA InfoCard	100.000.790
EC番号	200-868-2;
PubChem CID	522583;
UNII	4J67Y8SM0K ;
CompTox Dashboard (EPA)	DTXSID60996495 ;
	InChI InChI=1S/C2H7NO/c1-2(3)4/h2,4H,3H2,1H3 Key: UJPKMTDFFUTLGM-UHFFFAOYSA-N;
	SMILES CC(N)O;
性質
化学式	C2H7NO
モル質量	61.084 g·mol−1
外観	白色の結晶性固体
	特記無き場合、データは標準状態 (25 °C [77 °F], 100 kPa) におけるものである。

1-アミノエタノール（英語: 1-aminoethanol）は、化学式が CH₃CH(NH₂)OH の有機化合物である。アルカノールアミンに分類される。構造異性体の2-アミノエタノール（エタノールアミン）とはアミノ基の位置が異なる。1-アミノエタノールの中心炭素原子には4つの異なる置換基があるため、2つの立体異性体が存在する。

1-アミノエタノールは、アセトアルデヒドとアンモニア水溶液中に存在する^[1]。

1-アミノエタノールは、アラニン合成のストレッカー反応の中間体であることが示唆されている^[2]。

1-アミノエタノールは、1833年にヨハン・デーベライナーによって初めて合成され、組成式は1835年にユストゥス・フォン・リービッヒによって初めて決定された^[3]。分子構造は、1877年にロベルト・シフ（英語版）が CH₃CH(OH)NH₂ であることを示すまで、証明されないままであった^[4]。

出典

↑ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 0-471-72091-7
↑ 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.
↑ 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.
↑
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.

[1] Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 0-471-72091-7

[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.

[mwiw] Schiff, Robert (1877) "Zur Constitution des Chloralammoniaks und des Aldehydammoniaks," Berichte der Deutschen Chemischen Gesellschaft, 10 : 165–171.

[mwkA] Aschan, Ossian (1915) "Neues über Aldehyd-ammoniak und Chloral-ammoniak." Berichte der Deutschen Chemischen Gesellschaft, 48 (1) : 874–891.

[1]

[2]

[3]

[4]

出典

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