Bromoacetic acid

Bromoacetic acid
Names
	Preferred IUPAC name Bromoacetic acid
	Other names 2-Bromoacetic acid; Bromoethanoic acid; α-Bromoacetic acid; Monobromoacetic acid; Carboxymethyl bromide; UN 1938
Identifiers
CAS Number	79-08-3 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	506167
ChEMBL	ChEMBL60851 ;
ChemSpider	10301338;
ECHA InfoCard	100.001.069
EC Number	201-175-8;
PubChem CID	6227;
RTECS number	AF5950000;
UNII	2B3HS32431 ;
CompTox Dashboard (EPA)	DTXSID7021495 ;
	InChI InChI=1S/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5) Key: KDPAWGWELVVRCH-UHFFFAOYSA-N; InChI=1/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5) Key: KDPAWGWELVVRCH-UHFFFAOYAM;
	SMILES C(C(=O)O)Br; BrCC(O)=O;
Properties
Chemical formula	C2H3BrO2
Molar mass	138.948 g·mol−1
Appearance	White to light yellow crystalline solid
Density	1.934 g/mL
Melting point	49 to 51 °C (120 to 124 °F; 322 to 324 K)
Boiling point	206 to 208 °C (403 to 406 °F; 479 to 481 K)
Solubility in water	polar organic solvents
Acidity (pKa)	2.86
Refractive index (nD)	1.4804 (50 °C, D)
Structure
Crystal structure	Hexagonal or orthorhombic
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H311, H314, H317, H331, H400
GHS precautionary statements	P260, P261, P264, P270, P271, P272, P273, P280, P301+310, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P311, P312, P321, P322, P330, P333+313, P361, P363, P391, P403+233
NFPA 704 (fire diamond)	1 3 0
Flash point	110 °C (230 °F; 383 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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, such as by a Hell–Volhard–Zelinsky reaction^[3] or using other reagents.^[4]

CH₃CO₂H + Br₂ → CH₂BrCO₂H + HBr

References

^ Dippy, J.F.J., Hughes, S.R.C., Rozanski, A., J. Chem Soc., 1959, 2492.
^ "Bromoacetic acid". pubchem.ncbi.nlm.nih.gov.
^ Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405.
^ Natelson, S.; Gottfried, S. (1955). "Ethyl Bromoacetate". Organic Syntheses.; Collective Volume, 3, p. 381

External links

[1] Dippy, J.F.J., Hughes, S.R.C., Rozanski, A., J. Chem Soc., 1959, 2492.

[2] "Bromoacetic acid". pubchem.ncbi.nlm.nih.gov.

[Ullmann-3] Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405.

[4] Natelson, S.; Gottfried, S. (1955). "Ethyl Bromoacetate". Organic Syntheses.; Collective Volume, 3, p. 381

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Bromoacetic acid

See also

References

External links