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]
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| ECHA InfoCard | 100.003.214 |
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| Formula | C3H5ClO2 |
| Molar mass | 108.52 g·mol−1 |
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| Melting point | 42 °C (108 °F) |
| Boiling point | 204 °C (399 °F) (decomp.) |
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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] It has been demonstrated that the substance can be broken down by both bacteria and fungi as a means of bioremediation.[6][4]
References
edit- ^ 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.
- ^ Dixon SL, Jurs PC (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.
- ^ 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.
- ^ a b 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.
- ^ "Chemical Data Sheet for 3-CHLOROPROPIONIC ACID". NOAA.
- ^ Edbeib M (2020-04-15). "3-Chloropropionic Acid (3cp) Degradation and Production of Propionic Acid by Newly Isolated Fungus Trichoderma Sp. Mf1". International Journal of Life Sciences and Biotechnology. 3 (1): 41–50. doi:10.38001/ijlsb.677005. ISSN 2651-4621.
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