Ethyl bromoacetate

Structural formula
General
Surname	Ethyl bromoacetate
other names	Bromoacetic ester; Ethyl bromoacetate; EBA;
Molecular formula	C 4 H 7 BrO 2
Brief description	colorless liquid with an unpleasant odor
External identifiers / databases
EC number	203-290-9
ECHA InfoCard	100.002.992
PubChem	7748
Wikidata	Q413962
properties
Molar mass	167.01 g mol −1
Physical state	liquid
density	1.50 g cm −3 (20 ° C)
Melting point	−38 ° C
boiling point	159 ° C
Vapor pressure	3.5 hPa (25 ° C)
solubility	partial decomposition in water
Refractive index	1.4489 (20 ° C)
safety instructions
H and P phrases	H: 226-300 + 310 + 330
	P: 210-280-301 + 330 + 331 + 310-302 + 352 + 310-304 + 340 + 310-370 + 378
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Ethyl bromoacetate , also known as bromoacetate , is a halogenated aliphatic carboxylic acid ester . In its pure state, ethyl bromoacetate is a water-clear, foul smelling liquid with a boiling point of 159 ° C. The technical product has a yellowish color. Bromoacetic ester is very irritating to the eyes, there is a strong flow of tears, which quickly subsides in the fresh air.

use

In the early stages of the First World War, bromoacetic ester was used by the French army as a tear gas, a non-lethal chemical weapon.

During the Second World War it was used as a fragrance in Zyklon B to warn of the faintly smelling hydrogen cyanide.

In organic synthesis, bromoacetic ester is used as an alkylating reagent. It is sometimes used for ester condensations or for the production of ylides for Wittig reactions.

Ethyl bromoacetate as the starting point for a Wittig reaction sequence

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on ethyl bromoacetate in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-238.
↑ Entry on ethyl bromoacetate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers and / or distributors can expand the harmonized classification and labeling .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on ethyl bromoacetate in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[CRC90_3_238-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-238.

[CLP_100.002.992-3] Entry on ethyl bromoacetate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers and / or distributors can expand the harmonized classification and labeling .