Dichloroacetic acid

Dichloroacetic acid

Names
IUPAC name Dichloroacetic acid
Other names Dichloroethanoic acid, bichloroacetic acid, DCA, BCA, dichloracetic acid, bichloracetic acid
Identifiers
CAS Number	79-43-6 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:36386 Y
ChEMBL	ChEMBL13960 Y
ChemSpider	10771217 Y
DrugBank	DB08809 Y
ECHA InfoCard	100.001.098
KEGG	C11149 Y
MeSH	Dichloroacetate
PubChem	6597
RTECS number	AG6125000
UNII	9LSH52S3LQ Y
InChI InChI=1S/C2H2Cl2O2/c3-1(4)2(5)6/h1H,(H,5,6) Y Key: JXTHNDFMNIQAHM-UHFFFAOYSA-N Y InChI=1/C2H2Cl2O2/c3-1(4)2(5)6/h1H,(H,5,6) Key: JXTHNDFMNIQAHM-UHFFFAOYAK
SMILES ClC(Cl)C(O)=O
Properties
Chemical formula	C2H2Cl2O2
Molar mass	128.94 g·mol−1
Appearance	Colorless liquid
Density	1.5634 g/cm3 (20 °C)
Melting point	9 to 11 °C (48 to 52 °F; 282 to 284 K)
Boiling point	194 °C (381 °F; 467 K)
Solubility in water	miscible
Solubility	miscible with ethanol, diethyl ether
Acidity (pKa)	1.35
Magnetic susceptibility (χ)	-58.2·10−6 cm3/mol
Thermochemistry
Std enthalpy of formation (ΔfHo298)	−496.3 kJ·mol−1
Hazards
Safety data sheet	MSDS (jtbaker)
R-phrases	R35 R50
S-phrases	(S1/2) S26 S45 S61
NFPA 704	1 3 0
Related compounds
Related chloroacetic acids	Chloroacetic acid Trichloroacetic acid
Related compounds	Acetic acid Difluoroacetic acid Dibromoacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Dichloroacetic acid (DCA), sometimes called bichloroacetic acid (BCA), is the chemical compound with formula CHCl
2COOH. It is an acid, an analogue of acetic acid, in which 2 of the 3 hydrogen atoms of the methyl group have been replaced by chlorine atoms. Like the other chloroacetic acids, it has various practical applications. The salts and esters of dichloroacetic acid are called dichloroacetates. Salts of DCA have been studied as potential drugs because they inhibit the enzyme pyruvate dehydrogenase kinase.

Although preliminary studies have shown DCA can slow the growth of certain tumors in animal studies and in vitro studies, there is currently insufficient evidence to support the use of DCA for cancer treatment.

The chemistry of dichloroacetic acid is typical for halogenated organic acids. It is a member of the chloroacetic acids family. The dichloroacetate ion is produced when the acid is mixed with water. As an acid with a pK_a of 1.35, pure dichloroacetic acid is classed as a strong organic acid; it is very corrosive and extremely destructive to tissues of the mucous membranes and upper respiratory tract via inhalation.