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 Fluoroacetic 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.
Contents
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.
