Iodoacetic acid

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Iodoacetic acid
Names
IUPAC name
Iodoethanoic acid
Other names
2-Iodoacetic acid
Properties
C2H3O2I
Molar mass 185.948 g/mol
Appearance Whiteish crystalline solid
Odor Acetic
Density 2.2 g/cm3
Melting point 81 °C (178 °F; 354 K)
Boiling point 208 °C (406 °F; 481 K) (decomposes)
60 g/100 ml (20 ºC)
Solubility Soluble in diethyl ether, ethanol, methanol
Slightly soluble in chloroform
Vapor pressure 6.42 mmHg
Acidity (pKa) 3.18
Hazards
Safety data sheet Sigma-Aldrich
Related compounds
Related compounds
Acetic acid
Chloroacetic acid
Bromoacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Iodoacetic acid or monoiodoacetic acid is a derivative of acetic acid, an organoiodine compound.

Properties

Chemical

Iodoacetic acid is a powerful alkylating agent.

Physical

Iodoacetic acid is a white or yellowish crystalline solid, very soluble in water and organic solvents.

Availability

Due to its hazards, iodoacetic acid is hard to acquire.

Preparation

Iodoacetic acid can be prepared by treating chloroacetic acid with potassium iodide, reaction known as Finkelstein reaction:

Cl-CH2COOH + KI → I-CH2COOH + KCl

Projects

  • Alkylating agent

Handling

Safety

Iodoacetic acid is corrosive and highly poisonous. As the toxicity of monohaloacetic acids increases with halogen size, iodoacetic acid is more toxic than bromoacetic acid and much more toxic than chloroacetic acid.

Storage

Iodoacetic acid should be kept in closed bottles. It's recommended to be stored below 0 °C, in a special freezer, to limit sublimation or decomposition.

Disposal

Adding an excess of sodium hydroxide will convert it to the non-toxic sodium glycolate/glycolic acid.

References

Relevant Sciencemadness threads