Ethyl bromoacetate

Chembox new
Name = Ethyl bromoacetate
ImageFile = Ethyl-bromoacetate-2D-skeletal.png ImageName = Skeletal formula of ethyl bromoacetate
ImageFile1 = Ethyl-bromoacetate-3D-balls.png ImageName1 = Ball-and-stick model of ethyl bromoacetate
IUPACName = Ethyl bromoacetate
OtherNames = Bromoacetic acid
ethyl ester, Antol,
(Ethoxycarbonyl)-
methyl bromide
Section1 = Chembox Identifiers
SMILES = BrC(CO)OCC
CASNo = 105-36-2
RTECS = AF6000000
Section2 = Chembox Properties
Formula = C₄H₇O₂Br
MolarMass = 167.01 g/mol
Appearance = colourless to yellow liquid
Density = 1.51 g/cm³, liquid
Solubility = Insoluble
MeltingPt = -38 °C (199 K)
BoilingPt = 158 °C (431 K)
Viscosity =
Section3 = Chembox Structure
Dipole =
Section7 = Chembox Hazards
ExternalMSDS =
EUClass = Very toxic (T+)
NFPA-H = 3 | Flammability=2
NFPA-F =
NFPA-R =
RPhrases = R26/27/28
SPhrases = S1/2, S7/9, S26, S45
FlashPt = 47 °C
Section8 = Chembox Related
OtherAnions = Ethyl acetoacetate
Ethyl iodoacetate
Function = esters
OtherFunctn = Methyl bromoacetate
OtherCpds = Pepper spray
Chloropicrin

Ethyl 2-bromoacetate is the chemical compound with the formula CH₂BrCO₂C₂H₅. It is the ethyl ester of bromoacetic acid and is prepared in two steps from acetic acid [Natelson, S.; Gottfried, S. "Ethyl Bromoacetate" Organic Syntheses, Collected Volume 3, p.381 (1955). http://www.orgsyn.org/orgsyn/pdfs/CV3P0381.pdf (this procedure describes the conversion of acetic acid into bromoacetic acid).]

Applications

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, and was first employed for that purpose by French police in 1912. The French may have employed gas grenades of this substance in 1914 during World War I. The German army then used this attack to justify their subsequent employment of chemical weapons in 1915.cite web
last=Heller | first=Charles E. | date=September 1984
url=http://www-cgsc.army.mil/carl/resources/csi/Heller/HELLER.asp
title=Chemical Warfare in World War I: The American Experience, 1917-1918
publisher=Combat Studies Institute
accessdate=2007-08-02 ]

In organic synthesis, it is a versatile alkylating agent. Its major application involves the Reformatsky reaction, wherein it reacts with zinc to form a zinc enolate. The resulting BrZnCH₂CO₂Et condenses with carbonyl compounds to give a β-hydroxy-esters.

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:Ref|NOPWittig

References

# [http://www.chemicalland21.com/arokorhi/specialtychem/finechem/ETHYL%202-BROMOACETATE.htm Chemicalland properties database]
# [http://www.ehs.neu.edu/hazardeg.htm Environmental Health & Safety dept, Northeastern University]
# [http://www.who.int/entity/csr/delibepidemics/chapter3.pdf 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.