乙酰丙酮

乙酰丙酮
IUPAC名
pentane-2,4-dione
2,4-戊二酮
英文名 Acetylacetone
识别
缩写 Hacac
CAS号 123-54-6  checkY
ChemSpider 29001
SMILES
 
  • O=C(C)CC(=O)C
InChI
 
  • 1/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3
InChIKey YRKCREAYFQTBPV-UHFFFAOYAO
ChEBI 14750
KEGG C15499
性质
化学式 C5H8O2
摩尔质量 100.12 g·mol⁻¹
密度 0.98 g/mL
熔点 −23 °C(250 K)
沸点 140 °C(413 K)
溶解性 16 g / 100 mL
危险性
欧盟危险性符号
有害有害 Xn
警示术语 R:R10, R22
安全术语 S:S2, S21, S23, S24/25
NFPA 704
2
2
0
 
闪点 34°C
自燃温度 340°C
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

乙酰丙酮是一种有机化合物,缩写Hacac,其标准命名为2,4-戊二酮。它是一个双齿配体,并且在杂环化合物合成中有很多用处。

乙酰丙酮具有烯醇互变异构

制备

乙酰丙酮可由三氟化硼存在下,丙酮乙酸酐酰化制得。

(CH3CO)2O + CH3C(O)CH3 → CH3C(O)CH2C(O)CH3

也可由丙酮和乙酸乙酯缩合制得。

NaOEt + EtO2CCH3 + CH3C(O)CH3 → NaCH3C(O)CHC(O)CH3 + 2 EtOH
NaCH3C(O)CHC(O)CH3 + HCl → CH3C(O)CH2C(O)CH3 + NaCl

性质

乙酰丙酮具有弱酸性,pKa为8.94[1],可以和金属的氢氧化物反应,形成乙酰丙酮盐

参考资料

  1. ^ 2,4-Pentanedione. Retrieved from SciFinder. [2017-12-26]
  • 邢其毅等。《基础有机化学》第三版下册。北京:高等教育出版社,2005年。ISBN 978-7-04-017755-8

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