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3-Chloropropanoic acid

From Wikipedia, the free encyclopedia

3-Chloropropanoic acid
Identifiers
  • 3-chloropropionic acid
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.003.214 Edit this at Wikidata
Chemical and physical data
FormulaC3H5ClO2
Molar mass108.52 g·mol−1
3D model (JSmol)
Melting point42 °C (108 °F)
Boiling point204 °C (399 °F) (decomp.)
  • C(CCl)C(=O)O
  • InChI=1S/C3H5ClO2/c4-2-1-3(5)6/h1-2H2,(H,5,6)
  • Key:QEYMMOKECZBKAC-UHFFFAOYSA-N
  (verify)

3-Chloropropanoic acid (also known as 3-chloropropionic acid or UMB66) is the organic compound with the formula ClCH2CH2CO2H. A white or colorless solid, it is used as a drug and a synthetic intermediate. The compound is produced by the hydrochlorination of acrylic acid.[1] In aqueous solution, it has a pKa value of 4.08.[2]

This compound is used in scientific research. It is structurally related to GHB and binds to the GHB receptor, but has no affinity for GABA receptors.[3] It is also an active ingredient in some herbicide blends.[4] Overdose may cause unconsciousness and/or convulsions.[5]

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Transcription

References

  1. ^ Samel U, Kohler W, Gamer AO, Keuser U (2005). "Propionic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_223. ISBN 978-3527306732.
  2. ^ Dixon, Steven L.; Jurs, Peter C. (December 1993). "Estimation of p K a for organic oxyacids using calculated atomic charges". Journal of Computational Chemistry. 14 (12): 1460–1467. doi:10.1002/jcc.540141208. ISSN 0192-8651.
  3. ^ Macias AT, Hernandez RJ, Mehta AK, MacKerell AD, Ticku MK, Coop A (April 2004). "3-chloropropanoic acid (UMB66): a ligand for the gamma-hydroxybutyric acid receptor lacking a 4-hydroxyl group". Bioorganic & Medicinal Chemistry. 12 (7): 1643–1647. doi:10.1016/j.bmc.2004.01.025. PMID 15028257.
  4. ^ Ng HJ, Roswanira A, Ronald AC, Fahrul H (2005). "Degradation Of Herbicide (3-Chloropropionic Acid) By Bacterial Dehalogenases" (PDF). Proc. KUSTEM 4th Annual Seminar 2005: 586–590. Archived from the original (PDF) on 2016-03-05.
  5. ^ "Chemical Data Sheet for 3-CHLOROPROPIONIC ACID". NOAA.
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This page was last edited on 7 April 2024, at 09:33
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