Bromoacetic acid

Bromoacetic acid
IUPAC name 2-bromoacetic acid
Other names Bromoethanoic acid, α-Bromoacetic acid, Monobromoacetic acid, Carboxymethyl bromide, UN 1938
Identifiers
CAS number	79-08-3 Y
PubChem	6227
EC number	201-175-8
ChEMBL	CHEMBL60851 Y
RTECS number	AF5950000
Beilstein Reference	506167
Jmol-3D images	Image 1
SMILES C(C(=O)O)Br
InChI InChI=1/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5)
Properties
Molecular formula	C2H3BrO2
Molar mass	138.95 g mol−1
Appearance	White to light yellow crystalline solid
Density	1.934 g/mL
Melting point	49 - 51 °C
Boiling point	206 - 208 °C
Solubility in water	polar organic solvents
Acidity (pKa)	2.86[1]
Refractive index (nD)	1.4804 (50 °C, D)
Structure
Crystal structure	Hexagonal or orthorhombic
Hazards
R-phrases	R23/24/25, R36
S-phrases	S36/37/39, S45
Main hazards	Toxic (T), Corrosive {C)
NFPA 704	1 3 0
Flash point	110 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Bromoacetic acid is the chemical compound with the formula CH₂BrCO₂H. This colorless solid is a relatively strong alkylating agent. Bromoacetic acid and its esters are widely used building blocks in organic synthesis, for example in pharmaceutical chemistry.

The compound is prepared by bromination of acetic acid.^[2]

CH₃CO₂H + Br₂ → CH₂BrCO₂H + HBr

See also

• Acetic acid
• Chloroacetic acid
• Ethyl bromoacetate

References

1. ^ Dippy, J.F.J., Hughes, S.R.C., Rozanski, A., J. Chem Soc., 1959, 2492.
2. ^ Natelson, S.; Gottfried, S. (1955), "Ethyl Bromoacetate", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0381 ; Coll. Vol. 3: 381 

External links

• The microwave spectrum of bromoacetic acid
• Entry at chemicalland21.com