Methyl 2-bromoacetate
Names
Preferred IUPAC name
Methyl bromoacetate
Other names
Bromoacetic acid methyl ester, Methyl α-bromoacetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.273
EC Number
  • 202-499-2
UNII
  • InChI=1S/C3H5BrO2/c1-6-3(5)2-4/h2H2,1H3 checkY[PubChem]
    Key: YDCHPLOFQATIDS-UHFFFAOYSA-N
  • COC(=O)CBr
Properties
C3H5BrO2
Molar mass 152.975 g·mol−1
Density 1.6±0.1 g/cm3[1]
Boiling point 154 °C (309 °F; 427 K)
Solubility Soluble in water
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Warning
H301, H311, H314, H335
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 [77 °F], 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.[2] It is incompatible with acids, bases, oxidizing agents, and reducing agents.[3]

Application

Methyl bromoacetate is an alkylating agent. It has been used to alkylate phenol and amino groups.[4][5] Moreover, it can be used to make vitamins and pharmaceutical drugs. It is commonly used as a reagent in chemical modification of histidine.[2] In addition, methyl bromoacetate also use in synthesize of coumarins and cis-cyclopropane. It reacts with conjugated base and produce alkylated carbene complexes.[3]

Safety

Methyl bromoacetate can be toxic by ingestion and inhalation. It can also irritate the skin and eyes.[2]

See also

References

  1. ↑ "CSID:54945". ChemSpider. Retrieved 9 July 2017.
  2. 1 2 3 "Methyl Bromoacetate - Compound Summary for CID 60984". PubChem Compound Database. USA: National Center for Biotechnology Information. Identification. Retrieved 9 July 2017.
  3. 1 2 "A10605 Methyl bromoacetate, 98+%". Alfa Aesar. Retrieved 9 July 2017.
  4. ↑ Piątek, Piotr; Jurczak, Janusz (25 September 2002). "A selective colorimetric anion sensor based on an amide group containing macrocycle†". The Royal Society of Chemistry.
  5. ↑ 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.
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