Bromoacetic acid
| Names | |
|---|---|
| IUPAC name
Bromoethanoic acid
| |
| Systematic IUPAC name
Bromoethanoic acid | |
| Other names
2-Bromoacetic acid
α-Bromoacetic acid Carboxymethyl bromide Monobromoacetic acid UN 1938 | |
| Properties | |
| C2H3O2Br | |
| Molar mass | 138.948 g/mol |
| Appearance | White to light yellow crystalline solid |
| Odor | Vinegar-like |
| Density | 1.934 g/cm3 |
| Melting point | 50 °C (122 °F; 323 K) |
| Boiling point | 208 °C (406 °F; 481 K) |
| 175 g/100 ml (25 °C) | |
| Solubility | Soluble in acetone, benzene, diethyl ether, ethanol, isopropanol, methanol Slightly soluble in chloroform |
| Vapor pressure | 0.119 mmHg at 25 °C |
| Acidity (pKa) | 2.89 |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 110 °C (230 °F; 383 K) |
| Related compounds | |
| Related compounds
|
Acetic acid Fluoroacetic acid Chloroacetic acid Iodoacetic acid |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Bromoacetic acid is an organobromine chemical compound with the formula BrCH2COOH. It is a relatively strong alkylating agent.
Contents
Properties
Chemical
Bromoacetic acid can be hydrolyzed to glycolic acid in strong basic conditions.
Physical
Bromoacetic acid is a near-colorless solid, very soluble in water and alcohols.
Availability
Bromoacetic acid is sold by lab suppliers, but due to its toxicity, it's hard to acquire.
Preparation
Bromoacetic acid is prepared by bromination of acetic acid, in the presence of light.
- CH3COOH + Br2 → CH2BrCOOH + HBr
It can also be prepared by the Hell-Volhard-Zelinsky process:[1]
- CH3COOH + Br2 + Red phosphorus → CH2BrCOOH
Projects
- Alkylating agent
- Make glycolic acid
Handling
Safety
Bromoacetic acid is toxic by inhalation, ingestion and skin contact. It is corrosive to metals and tissue. Wear gloves, goggles and an apron when handling the compound, and make sure you do not breathe the fumes.
Storage
In closed bottles.
Disposal
Excess alkali will hydrolyze it to glycolic acid and sodium glycolate, which have low toxicity.
