Chloroacetic acid

Chloroacetic acid
IUPAC name	Chloroacetic acid
Systematic name	Chloroethanoic acid
Identifiers
CAS number	79-11-8 Y
RTECS number	AF8575000
Properties
Molecular formula	C2H3ClO2
Molar mass	94.50 g mol−1
Appearance	Colourless or white crystals
Density	1.58 g cm−3, solid
Melting point	63 °C
Boiling point	189 °C
Solubility in water	Soluble
Acidity (pKa)	2.87[1]
Hazards
MSDS	External MSDS
R-phrases	25-34-50
S-phrases	23-37-45-61
NFPA 704	1 3 0
Flash point	126 °C
Related compounds
Related compounds	2-chloropropionic acid sodium chloroacetate
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Chloroacetic acid is the chemical compound with the formula ClCH₂CO₂H. This carboxylic acid is a useful building block in organic synthesis. Like other chloroacetic acids and related halocarbons, it is a potentially dangerous alkylating agent.

Chloroacetic acid is synthesized by the chlorination of acetic acid in the presence of red phosphorus, sulfur, or iodine as a catalyst:

CH₃CO₂H + Cl₂ → ClCH₂CO₂H + HCl

It also forms by the hydrolysis of trichloroethylene using sulfuric acid as a catalyst.

Illustrative of its usefulness in organic chemistry is the O-alkylation of salicylaldehyde with chloroacetic acid, followed by decarboxylation of the resulting ether, produces benzofuran.^[2]

References

1. ^ Ionization Constants of Heteroatom Organic Acids
2. ^ Burgstahler, A. W.; Worden, L. R. (1966). "Coumarone." Org. Synth. 46: 28.

See also

• Chloroacetic acids
• Dichloroacetic acid
• Trichloroacetic acid
• Chloracetyl chloride

External links

• "Monochloroacetic Acid". Dow Chemical. http://www.dow.com/webapps/lit/litorder.asp?filepath=gco/pdfs/noreg/103-00133.pdf&pdf=true. Retrieved 20 May 2007. 
• "Monochloroacetic Acid". IPCS Inchem. http://www.inchem.org/documents/pims/chemical/pim352.htm. Retrieved 20 May 2007.