Chemistry:Acetonedicarboxylic acid
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| Preferred IUPAC name
3-Oxopentanedioic acid | |
Other names
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3D model (JSmol)
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| Properties | |
| C5H6O5 | |
| Molar mass | 146.09814 g/mol |
| 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 | |
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| GHS Signal word | Warning |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, 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). | |
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Tracking categories (test):
Acetonedicarboxylic acid, 3-oxoglutaric acid or β-ketoglutaric acid is a simple dicarboxylic acid.
Preparation
Acetonedicarboxylic acid can also be prepared by decarboxylation of citric acid in fuming sulfuric acid:[2]
Applications
Acetonedicarboxylic acid and its esters such as dimethylacetonedicarboxylate are primarily used as building blocks in the synthesis of heterocyclic rings[3] and in the Weiss–Cook reaction.[4]
Acetonedicarboxylic acid is well known to be used in the Robinson tropinone synthesis.
The presence of β-ketoglutaric acid in human urine is diagnostic for the harmful gut flora such as Candida albicans.[5]
See also
References
- ↑ |ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC 1,3-Acetonedicarboxylic acid{{|bot=InternetArchiveBot |fix-attempted=yes }} at Sigma-Aldrich (safety data sheet)
- ↑ Roger Adams; H. M. Chiles; C. F. Rassweiler (1925). "Acetonedicarboxylic Acid". Organic Syntheses 5: 5. doi:10.15227/orgsyn.005.0005.
- ↑ 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. 100. pp. 145–174. doi:10.1016/S0065-2725(10)10005-1. ISBN 9780123809360.
- ↑ Korman, Matthew; Paz, Eric; Franklin, Tylor; Lewandowski, Nicholas R.; Sullivan, Bethany; Imhoff, Andrea M.; Fisher, Luke; Bichler, Katherine A. et al. (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. doi:10.1021/acs.jchemed.9b00653. Bibcode: 2020JChEd..97.3835K.
- ↑ Schmidt, Michael A, Tired of Being Tired: Overcoming Chronic Fatigue and Low Energy
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