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Dichloroacetate

Dichloroacetic acid
Dichloroacetic-acid-2D-skeletal.png
Dichloroacetic-acid-3D-vdW.png
Names
IUPAC name
Dichloroacetic acid
Other names
Dichloroethanoic acid, bichloroacetic acid, DCA, BCA, dichloracetic acid, bichloracetic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.001.098
KEGG
MeSH Dichloroacetate
PubChem CID
RTECS number AG6125000
UNII
Properties
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)
miscible
Solubility miscible with ethanol, diethyl ether
Acidity (pKa) 1.35
-58.2·10−6 cm3/mol
Thermochemistry
−496.3 kJ·mol−1
Hazards
Safety data sheet MSDS (jtbaker)
R-phrases (outdated) R35 R50
S-phrases (outdated) (S1/2) S26 S45 S61
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Related compounds
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).
YesY  (what is YesYN ?)
Infobox references

Dichloroacetic acid (DCA), sometimes called bichloroacetic acid (BCA), is the chemical compound with formula CHCl
2
COOH
. It is an acid, an analogue of acetic acid, in which 2 of the 3 hydrogen atoms of the methyl group have been replaced by chlorine atoms.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, as of 2012 there is 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 pKa 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.


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