Bromoacetic acid

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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
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.

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

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.

References

  1. http://www.prepchem.com/synthesis-of-bromoacetic-acid/

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