Standard Article

Acetoacetic Acid

  1. Shridhar G. Hegde

Published Online: 15 APR 2001

DOI: 10.1002/047084289X.ra010

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Hegde, S. G. 2001. Acetoacetic Acid. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. Monsanto Company, St. Louis, MO, USA

Publication History

  1. Published Online: 15 APR 2001

Chemistry Terms

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Abstract

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[541-50-4] C4H6O3 (MW 102.09)

(acetone enolate equivalent in alkylations,2 carbonyl additions,3 conjugate additions,4 and diazonium ion coupling reactions5)

Alternate Names:3-oxobutanoic acid.

Physical Data: mp 36–37 °C; pKa 3.58; enol content: carbon tetrachloride (35 °C), 49%; DMSO-d6 (35 °C), 10.8%; D2O (0 °C), <2%.6

Solubility: sol H2O, alcohol.

Preparative Methods: traditionally prepared by base hydrolysis of Ethyl Acetoacetate.3, 7 A high yield synthesis by acid hydrolysis of Diketene is also reported.6

Handling, Storage, and Precautions:acetoacetic acid is extremely hygroscopic but can be stored under vacuum in a freezer for several weeks with little change. It decomposes rapidly to acetone and carbon dioxide when heated above the melting point. Use in a fume hood.

Featured Compounds

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  1. 1 - 25
Compound Information
Molecular Weight:127.1842
Molecular Formula:C7H13NO
InChIKey:ZAJDAGLJUKMNJL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:457.428
Molecular Formula:C8H14I2N2Zn
InChIKey:UQKIENOVYWWYFI-UHFFFAOYSA-L
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Compound Information
Molecular Weight:179.2004
Molecular Formula:C6H18N3OP
InChIKey:GNOIPBMMFNIUFM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:SYOVWIRLZABVDO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.1858
Molecular Formula:C10H10O
InChIKey:BWHOZHOGCMHOBV-BQYQJAHWSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:FWFSEYBSWVRWGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.2979
Molecular Formula:C15H14N4O
InChIKey:BQKCJZTWOQOUSP-KRFFEMNTSA-N
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Compound Information
Molecular Weight:140.57
Molecular Formula:C6H5ClN2
InChIKey:CLRSZXHOSMKUIB-UHFFFAOYSA-M
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Compound Information
Molecular Weight:185.061
Molecular Formula:C8H9Br
InChIKey:CRRUGYDDEMGVDY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:MUVVFSVVVHYLMQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:93.1265
Molecular Formula:C6H7N
InChIKey:PAYRUJLWNCNPSJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.1885
Molecular Formula:C9H10N2O
InChIKey:PWELTGGNVDVIGR-JXMROGBWSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:RJMIBGCTYAZHJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:209.1986
Molecular Formula:C10H11NO4
InChIKey:QLWGGIGZONFVIO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:NVPCGXUWUBHZBD-NSCUHMNNSA-N
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Compound Information
Molecular Weight:151.1195
Molecular Formula:C7H5NO3
InChIKey:CMWKITSNTDAEDT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:ZCFOBLITZWHNNC-VOTSOKGWSA-N
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Compound Information
Molecular Weight:82.0338
Molecular Formula:C2H3NaO2
InChIKey:VMHLLURERBWHNL-UHFFFAOYSA-M
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:HGBOYTHUEUWSSQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:64.055
Molecular Formula:C4H9Li
InChIKey:MZRVEZGGRBJDDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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