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| Names | |
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| Preferred IUPAC name Methyl bromoacetate | |
| Other names Bromoacetic acid methyl ester, Methyl α-bromoacetate | |
| Identifiers | |
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| 3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.002.273 
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| EC Number |
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| PubChem CID | |
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| CompTox Dashboard (EPA) | |
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| Properties | |
| Chemical formula | C3H5BrO2 |
| Molar mass | 152.975 g·mol |
| Density | 1.6±0.1 g/cm |
| Boiling point | 154 °C (309 °F; 427 K) |
| Solubility | Soluble in water |
| Hazards | |
| GHS labelling: | |
| Pictograms |   
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| Signal word | Warning |
| Hazard statements | H301, H311, H314, H335 |
| Precautionary statements | P233, P260, P261, P264, P270, P271, P280, P301, P302, P303, P304, P305, P310, P312, P321, P322, P330, P331, P338, P340, P351, P352, P353, P361, P363, P403, P405, P501 |
| Flash point | 63 °C (145 °F; 336 K) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references | |
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.
See also
References
- "CSID:54945". ChemSpider. Retrieved 9 July 2017.
- ^ "Methyl Bromoacetate - Compound Summary for CID 60984". PubChem Compound Database. USA: National Center for Biotechnology Information. Identification. Retrieved 9 July 2017.
- ^ "A10605 Methyl bromoacetate, 98+%". Alfa Aesar. Retrieved 9 July 2017.
- Piątek, Piotr; Jurczak, Janusz (25 September 2002). "A selective colorimetric anion sensor based on an amide group containing macrocycle†". The Royal Society of Chemistry. PMID 12430485.
- Raju, B.; Murphy, E.; Levy, L.A.; Hall, R.D.; London, R.E. (1 March 1989). "A fluorescent indicator for measuring cytosolic free magnesium". The American Journal of Physiology. 256 (3 Pt 1): C540-8. doi:10.1152/ajpcell.1989.256.3.C540. PMID 2923192.
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. 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.