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542-05-2 - Acetone-1,3-dicarboxylic acid, 97% - 3-Ketoglutaric acid - 3-Oxoglutaric acid - A13742 - Alfa Aesar

A13742 Acetone-1,3-dicarboxylic acid, 97%

CAS Number
542-05-2
Synonyms
3-Ketoglutaric acid
3-Oxoglutaric acid

Size Price ($) Quantity Availability
50g 31.93
250g 125.66
1000g 302.40
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Acetone-1,3-dicarboxylic acid, 97%

MDL
MFCD00002711
EINECS
208-797-9

Chemical Properties

Formula
C5H6O5
Formula Weight
146.10
Melting point
ca 132° dec.
Sensitivity
Hygroscopic
Solubility
Soluble in water and alcohol. Slightly soluble in ethyl acetate and ether. Insoluble in chloroform.

Applications

Acetone-1,3-dicarboxylic acid is used as a building block in organic chemistry. It is also used in the synthesis of hetrocyclic rings and in the Weiss-Cook reaction, which involves the preparation of cis-bicyclo[3.3.0]octane-3,7-dione by reacting with diacyl (1,2 ketone). Its presence in human urine is used as a diagnostic test for the overgrowth of harmful gut flora such as Candida albicans.

Notes

Hygroscopic. Incompatible with strong bases and strong oxidizing agents.

Literature References

For use in Robinson's classical one-step synthesis of pseudopelletierine, see: Org. Synth. Coll., 4, 816 (1963):

For a more recent analogous example of the synthesis of azabicyclo[3.3.1]nonan-3-one derivatives, see: J. Med. Chem., 36, 3707 (1993).

Li, C.; Breit, B. Rhodium-Catalyzed Chemo- and Regioselective Decarboxylative Addition of beta-Ketoacids to Allenes: Efficient Construction of Tertiary and Quaternary Carbon Centers. J. Am. Chem. Soc. 2014, 136 (3), 862-865.

Sousa, A.; Araújo, P.; Mateus, N.; de Freitas, V. Deoxyvitisins: a new set of pyrano-3-deoxyanthocyanidins. Tetrahedron Lett. 2013, 54 (35), 4785-4788.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,68
Beilstein
1447081
Harmonized Tariff Code
2918.30
TSCA
Yes

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