Methyl 2-bromoacetate (methyl bromoactate) is a chemical compound with the molecular formula C3H5BrO2.
Properties Methyl 2-bromoacetate is colorless or straw-colored liquid. The smell is sharp and penetrating. It is soluble in water and also has a higher density than water. It is incompatible with acids, bases, oxidizing agents, and reducing agents.
Application Methyl bromoacetate is an alkylating agent. It has been used to alkylate phenol and amino groups. Moreover, it can be used to make vitamins and pharmaceutical drugs. It is commonly used as a reagent in chemical modification of histidine. In addition, methyl bromoacetate also use in synthesize of coumarins and cis-cyclopropane. It reacts with conjugated base and produce alkylated carbene complexes.
Safety Methyl bromoacetate can be toxic by ingestion and inhalation. It can also irritate the skin and eyes as it is a lachrymator.
See also Ethyl bromoacetate
References
Extra reading Raju, B.; Murphy, E.; Levy, L. A.; Hall, R. D.; London, R. E. (1 March 1989). "A fluorescent indicator for measuring cytosolic free magnesium". American Journal of Physiology. Cell Physiology. 256 (3): C540–C548. doi:10.1152/ajpcell.1989.256.3.C540. PMID 2923192. Upper, Christen D.; West, Charles A. (July 1967). "Biosynthesis of Gibberellins". Journal of Biological Chemistry. 242 (14): 3285–3292. doi:10.1016/S0021-9258(18)95908-9. Davis, Franklin A.; Zhou, Ping; Reddy, G. Venkat (June 1994). "Asymmetric Synthesis and Reactions of cis-N-(p-Toluenesulfinyl)aziridine-2-carboxylic Acids". The Journal of Organic Chemistry. 59 (12): 3243–3245. doi:10.1021/jo00091a001. Henderson, Jaclyn L.; Edwards, Andrew S.; Greaney, Michael F. (June 2006). "Three-Component Coupling of Benzyne: Domino Intermolecular Carbopalladation". Journal of the American Chemical Society. 128 (23): 7426–7427. Bibcode:2006JAChS.128.7426H. doi:10.1021/ja0615526. PMID 16756281. Hannick, Steven M.; Kishi, Yoshito (October 1983). "An improved procedure for the Blaise reaction: a short, practical route to the key intermediates of the saxitoxin synthesis". The Journal of Organic Chemistry. 48 (21): 3833–3835. doi:10.1021/jo00169a053.





