Ethyl bromoacetate
From Wikipedia, the free encyclopedia
| Ethyl bromoacetate | |
|---|---|
 |
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| General | |
| Systematic name | Ethyl bromoacetate |
| Other names | Bromoacetic acid ethyl ester, Antol, (Ethoxycarbonyl)- methyl bromide |
| Molecular formula | C4H7O2Br |
| SMILES | BrC(CO)OCC |
| Molar mass | 167.01 g/mol |
| Appearance | colourless to yellow liquid |
| CAS number | [105-36-2] |
| Properties | |
| Density and phase | 1.51 g/cm3, liquid |
| Solubility in water | Insoluble |
| Melting point | -38 °C (199 K) |
| Boiling point | 158 °C (431 K) |
| Viscosity | ? cP at ? °C |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| EU classification | Very toxic (T+) |
| NFPA 704 (estimate) |
2
3
0
|
| R-phrases | R26/27/28 |
| S-phrases | S1/2, S7/9, S26, S45 |
| Flash point | 47 °C |
| RTECS number | AF6000000 |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Other anions | Ethyl acetoacetate Ethyl iodoacetate |
| Related esters | Methyl bromoacetate |
| Related compounds | Pepper spray Chloropicrin |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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The chemical compound ethyl 2-bromoacetate is a chemical intermediate for the production of many organic compounds, such as drugs, cosmetics, agricultural chemicals, and pharmaceuticals. Chemically, it is the ethyl ester of bromoacetic acid.
[edit] Applications
Historically in World War I, ethyl bromoacetate was used as a lachrymatory agent and tear gas agent for chemical warfare under the German code Weisskreuz (White Cross), and later as odorant or warning agent in odourless, toxic gases. It is listed by the WHO as a riot control agent.
In organic synthesis, a major application is in the Reformatskii reaction, where it reacts with zinc to form a zinc enolate which then condenses with a carbonyl compound to form a β-hydroxy-ester.
It is also the starting point for the preparation of several other reagents. For example, the related Wittig reagent (prepared by reaction with triphenylphosphine) is commonly used to prepare alpha,beta-unsaturated esters from carbonyl compounds such as benzaldehyde:
[edit] References
- European Chemicals Bureau
- Chemicalland properties database
- Environmental Health & Safety dept, Northeastern University
- Public health response to biological and chemical weapons, Chapter 3 Biological and Chemical agents, WHO Guidance
- ↑ A student lab procedure for the Wittig sequence shown, only using the related methyl ester.
