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Methyl 2-bromoacetate

From Wikipedia, the free encyclopedia
Methyl 2-bromoacetate
Names
Preferred IUPAC name
Methyl bromoacetate
Other names
Bromoacetic acid methyl ester, Methyl α-bromoacetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.002.273Edit this at Wikidata
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 mass152.975 g·mol−1
Density1.6±0.1 g/cm3[1]
Boiling point154 °C (309 °F; 427 K)
SolubilitySoluble 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 point63 °C (145 °F; 336 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Methyl 2-bromoacetate (methyl bromoactate) is a chemical compound with the molecular formula C3H5BrO2.

Properties

[edit]

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

[edit]

Methyl bromoacetate is analkylating agent. It has been used to alkylatephenol andamino groups.[4][5] Moreover, it can be used to makevitamins andpharmaceutical 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

[edit]

Methyl bromoacetate can be toxic by ingestion and inhalation. It can also irritate the skin and eyes as it is a lachrymator.[2]

See also

[edit]

References

[edit]
  1. ^"CSID:54945". ChemSpider. Retrieved9 July 2017.
  2. ^abc"Methyl Bromoacetate - Compound Summary for CID 60984".PubChem Compound Database. USA: National Center for Biotechnology Information. Identification. Retrieved9 July 2017.
  3. ^ab"A10605 Methyl bromoacetate, 98+%". Alfa Aesar. Retrieved9 July 2017.
  4. ^Piątek, Piotr; Jurczak, Janusz (25 September 2002). "A selective colorimetric anion sensor based on an amide group containing macrocycle".Chemical Communications (20):2450–2451.doi:10.1039/b207335h.PMID 12430485.
  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

[edit]
  • 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.
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