Acetonedicarboxylic acid

Acetonedicarboxylic acid[1]
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
3-Oxopentanedioic acid
Other names
  • 1,3-Acetonedicarboxylic acid
  • 3-oxoglutaric acid
  • 3-ketoglutaric acid
  • β-ketoglutaric acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.999
EC Number
  • 208-797-9
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10) checkY
    Key: OXTNCQMOKLOUAM-UHFFFAOYSA-N checkY
  • InChI=1/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10)
    Key: OXTNCQMOKLOUAM-UHFFFAOYAR
SMILES
  • C(C(=O)CC(=O)O)C(=O)O
  • O=C(O)CC(=O)CC(=O)O
Properties
Chemical formula
 C5H6O5
Molar mass 146.09814 g/mol
Appearance colorless or white solid
Density 1.499 g/cm3
Melting point 122 °C (252 °F; 395 K) (decomposes)
Boiling point 408.4 °C (767.1 °F; 681.5 K) (760mm Hg)
Hazards
GHS labelling:
Pictograms
 GHS07: Exclamation mark
Signal word
 Warning
Hazard statements
 H315, H319, H335
Precautionary statements
 P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 214.9 °C (418.8 °F; 488.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Acetonedicarboxylic acid is the organic compound with the formula O=C(CH2CO2H)2. It is classified as both a dicarboxylic acid and an oxocarboxylic acid.[2]

Preparation

Acetonedicarboxylic acid is prepared commercially by oxidation of citric acid.[2] It can also be prepared by treating citric acid with fuming sulfuric acid.[3]

Reactions and uses

Upon heating it undergoes decarboxylation first to give acetoacetic acid then acetone:[2]

O=C(CH2CO2H → O=C(CH3)(CO2H) + CO2
O=C(CH3)(CO2H) → O=C(CH3)2 + CO2

Acetonedicarboxylic acid and its esters such as dimethylacetonedicarboxylate are primarily used as building blocks in the synthesis of heterocycles[4] One example is it use in Robinson's classic synthesis of tropinone. It participates in the Weiss–Cook reaction.[5]

See also

References

  1. ^ |ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC 1,3-Acetonedicarboxylic acid{{|bot=InternetArchiveBot |fix-attempted=yes }} at Sigma-Aldrich (safety data sheet)
  2. ^ a b c Klingler, Franz Dietrich; Ebertz, Wolfgang (2000). "Oxocarboxylic Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a18_313. ISBN 978-3-527-30385-4.
  3. ^ Roger Adams; H. M. Chiles; C. F. Rassweiler (1925). "Acetonedicarboxylic Acid". Organic Syntheses. 5: 5. doi:10.15227/orgsyn.005.0005.
  4. ^ Stanovnik, Branko; Grošelj, Uroš (2010). "Dialkyl Acetone-1,3-Dicarboxylates and their Mono- and bis(Dimethylamino)methylidene Derivatives in the Synthesis of Heterocyclic Systems". Advances in Heterocyclic Chemistry Volume 100. Vol. 100. pp. 145–174. doi:10.1016/S0065-2725(10)10005-1. ISBN 9780123809360.
  5. ^ Korman, Matthew; Paz, Eric; Franklin, Tylor; Lewandowski, Nicholas R.; Sullivan, Bethany; Imhoff, Andrea M.; Fisher, Luke; Bichler, Katherine A.; Van Ornum, Scott G. (2020). "Process Development of the Weiss–Cook Reaction for the Preparation of cis-1,5-Dimethylbicyclo[3.3.0]octane-3,7-dione in the Undergraduate Organic Laboratory". Journal of Chemical Education. 97 (10): 3835–3838. Bibcode:2020JChEd..97.3835K. doi:10.1021/acs.jchemed.9b00653. S2CID 225248640.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.