Ethyl bromoacetate

Ethyl bromoacetate

Names
Preferred IUPAC name Ethyl bromoacetate
Other names Ethyl 2-bromoacetate Bromoacetic acid, ethyl ester Antol Ethoxycarbonylmethyl bromide
Identifiers
CAS Number	105-36-2 Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL1085948 Y
ChemSpider	7462 Y
ECHA InfoCard	100.002.992
PubChem	7748
RTECS number	AF6000000
UNII	D20KFB313W Y
InChI InChI=1S/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3 Y Key: PQJJJMRNHATNKG-UHFFFAOYSA-N Y InChI=1/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3 Key: PQJJJMRNHATNKG-UHFFFAOYAE
SMILES BrCC(=O)OCC
Properties
Chemical formula	C4H7BrO2
Molar mass	167.00 g·mol−1
Appearance	Colorless to yellow liquid
Density	1.51 g/cm3
Melting point	−38 °C (−36 °F; 235 K)
Boiling point	158 °C (316 °F; 431 K)
Solubility in water	Insoluble
Magnetic susceptibility (χ)	-82.8·10−6 cm3/mol
Hazards
EU classification (DSD)	Very toxic (T+), Powerful lachrymator, Extremely harmful,
R-phrases	R26/27/28
S-phrases	(S1/2), S7/9, S26, S45
NFPA 704	0 4 3
Flash point	47 °C (117 °F; 320 K)
Related compounds
Other anions	Ethyl acetoacetate Ethyl iodoacetate
Related esters	Methyl bromoacetate
Related compounds	Pepper spray Chloropicrin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Ethyl 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. It is a lachrymator and has a fruity, pungent odor. It is also a highly toxic alkylating agent and may be fatal if inhaled.

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 odorless, toxic gases. It is listed by the World Health Organization 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.

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: