2,2-Dichloropropionic acid

2,2-Dichloropropionic acid is the organic compound with the formula CH₃CCl₂CO₂H.^[1] It is a colorless liquid that freezes near room temperature.

2,2-Dichloropropionic acid

Names
Preferred IUPAC name 2,2-Dichloropropanoic acid
Identifiers
CAS Number	75-99-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:81859
ChEMBL	ChEMBL445525
ChemSpider	6178
ECHA InfoCard	100.000.840
EC Number	200-923-0
KEGG	C18600
PubChem CID	6418
RTECS number	UF0690000
UNII	VO6PY8ZMRW
UN number	1760
CompTox Dashboard (EPA)	DTXSID2021575
InChI InChI=1S/C3H4Cl2O2/c1-3(4,5)2(6)7/h1H3,(H,6,7) Key: NDUPDOJHUQKPAG-UHFFFAOYSA-N
SMILES CC(C(=O)O)(Cl)Cl
Properties
Chemical formula	C3H4Cl2O2
Molar mass	142.96 g·mol−1
Appearance	colorless oil
Density	1.40 g/cm3 (20 °C)
Melting point	20 °C (68 °F; 293 K)
Boiling point	190 °C (374 °F; 463 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H315, H318, H412
Precautionary statements	P264, P273, P280, P302+P352, P305+P351+P338, P310, P321, P332+P313, P362, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Occurrence and use

Its sodium salt once was marketed under the name Dalapon as a selective herbicide used to control perennial grasses.^[2]

It is an inhibitor of some enzymes that process pyruvate.^[3]

References

1. Samel, Ulf-Rainer; Kohler, Walter; Gamer, Armin Otto; Keuser, Ullrich (2005). "Propionic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_223. ISBN 978-3527306732.
2. "Dalapon". pmep.cce.cornell.edu. Retrieved 2016-08-31. (dead link 24 August 2024)
3. Halestrap, A. P. (1975). "The mitochondrial pyruvate carrier. Kinetics and specificity for substrates and inhibitors". Biochemical Journal. 148 (1): 85–96. doi:10.1042/bj1480085. PMC 1165509. PMID 1156402.