3-Chloropropanoic acid

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 pK_a value of 4.08.^[2]

3-Chloropropanoic acid

Identifiers
IUPAC name 3-chloropropionic acid
CAS Number	107-94-8 Y
PubChem CID	7899
ChemSpider	7611
UNII	R5J180FN9Z
CompTox Dashboard (EPA)	DTXSID5021546
ECHA InfoCard	100.003.214
Chemical and physical data
Formula	C3H5ClO2
Molar mass	108.52 g·mol−1
3D model (JSmol)	Interactive image
Melting point	42 °C (108 °F)
Boiling point	204 °C (399 °F) (decomp.)
SMILES C(CCl)C(=O)O
InChI InChI=1S/C3H5ClO2/c4-2-1-3(5)6/h1-2H2,(H,5,6) Key:QEYMMOKECZBKAC-UHFFFAOYSA-N
(verify)

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

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 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.
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.
6. 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.