World Library  
Flag as Inappropriate
Email this Article

Ethyl acetoacetate

Article Id: WHEBN0002726743
Reproduction Date:

Title: Ethyl acetoacetate  
Author: World Heritage Encyclopedia
Language: English
Subject: Pyrimidine, Biginelli reaction, Knorr pyrrole synthesis, EAA, Ethyl bromoacetate
Collection:
Publisher: World Heritage Encyclopedia
Publication
Date:
 

Ethyl acetoacetate

Ethyl acetoacetate
Skeletal formula of ethyl acetoacetate
Space-filling model of the ethyl acetoacetate molecule
Names
IUPAC name
Ethyl 3-oxobutanoate
Other names
Acetoacetic acid ethyl ester
Ethyl acetylacetate
3-Oxobutanoic acid ethyl ester
Identifiers
 Y
ChEMBL  Y
ChemSpider  Y
Jmol-3D images Image
KEGG  Y
RTECS number AK5250000
UNII  Y
Properties
C6H10O3
Molar mass 130.14 g/mol
Appearance Colourless liquid
Odor fruit or rum
Density 1.021 g/cm3, liquid
Melting point −45 °C (−49 °F; 228 K)
Boiling point 180.8 °C (357.4 °F; 454.0 K)
2.86 g/100 ml (20 °C)
Acidity (pKa) 10.68 (in H2O)
14.2 (in DMSO)
Hazards
not listed
NFPA 704
2
2
Flash point 70 °C (158 °F; 343 K)
Related compounds
Related esters
Methyl acetoacetate
Ethyl acetate
Diethyl malonate
Related compounds
Acetone
Acetylacetone
Diketene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

The ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine and aminopyrine, and vitamin B1; as well as the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food.

Contents

  • Preparation 1
  • Reactivity 2
  • See also 3
  • References 4
  • External links 5

Preparation

Ethyl acetoacetate is produced industrially by treatment of diketene with ethanol.[1]

The preparation of ethyl acetoacetate is a classic laboratory procedure.[2] It is prepared via the Claisen condensation of ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol.

Preparation of ethyl acetoacetate.

Reactivity

Ethyl acetoacetate is subject to Keto-enol tautomerism. Ethyl acetoacetate is often used in the acetoacetic ester synthesis similar to diethyl malonate in the malonic ester synthesis or the Knoevenagel condensation. The protons alpha to carbonyl groups are acidic, and the resulting carbanion can undergo nucleophilic substitution. A subsequent thermal decarboxylation is also possible.[3] Similar to the behavior of acetylacetone, the enolate of ethyl acetoacetate can also serve as a bidentate ligand. For example, it forms purple coordination complexes with iron(III) salts:

Ethyl acetoacetate can also be reduced to ethyl 3-hydroxybutyrate.

See also

  • Fructone, the ethylene glycol ketal of ethyl acetoacetate, an aroma compound

References

  1. ^ Wilhelm Riemenschneider and Hermann M. Bolt "Esters, Organic" Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a09_565.pub2
  2. ^ J. K. H. Inglis and K. C. Roberts (1926). "Ethyl Acetoacetate".  
  3. ^ Carey, Francis A. (2006). Organic Chemistry (Sixth ed.). New York, NY: McGraw-Hill.  

External links

  • International Chemical Safety Card 1024
  • Inchem properties database
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.
 


Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.