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CAS NO:105-36-2
EC NO:203-290-9
Ethyl bromoacetate is the chemical compound with the formula CH2BrCO2C2H5.
Ethyl bromoacetate is the ethyl ester of bromoacetic acid and is prepared in two steps from acetic acid.
Ethyl bromoacetate is a lachrymator and has a fruity, pungent odor.
Ethyl bromoacetate is also a highly toxic alkylating agent and may be fatal if inhaled.
Properties
Chemical formula C4H7BrO2
Molar mass 167.002 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
Applications
Ethyl bromoacetate 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 army used rifle grenades 'grenades lacrymogènes' filled with this gas against the Germans beginning in August 1914, but the weapons were largely ineffective, even though ethyl bromoacetate is twice as toxic as chlorine.
In the early months of the war the British also used the weaponized use of tear gas agents and more toxic gasses including sulfur dioxide. The German army then used these attacks to justify their subsequent employment of it as odorant or warning agent in odorless, toxic gases and chemical weapons in 1915 under the German code Weisskreuz (White Cross).
In organic synthesis, Ethyl bromoacetate is a versatile alkylating agent.
Ethyl bromoacetates 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.
Ethyl bromoacetate is also the starting point for the preparation of several other reagents.
General description
Ethyl bromoacetate on derivatisation reaction with p-t-butyl calix[4]arene yields 1,3-diester substituted calix[4]arene.
Ethyl bromoacetate also undergoes Suzuki type cross-coupling reactions with arylboronic acids cocatalyzed by copper(I) oxide.
Application
Ethyl bromoacetate was used to prepare reversibly photoresponsive coumarin-stabilized polymeric nanoparticles in an aqueous medium, which act as a detectable drug carrier.
Ethyl bromoacetate appears as a clear, colorless liquid. A lachrymator. Toxic by ingestion, inhalation and skin absorption; a strong irritant of the skin. Insoluble in water and soluble in alcohol, benzene, and ether.
Ethyl bromoacetate is widely used as an alkylating reagent involved in the Reformatsky reaction to prepare the beta-hydroxy esters by reacting with carbonyl compounds.
Ethyl bromoacetate is also used for the syntheses of witting reagent, artificial diethylstilbestrol antigen, 3-phenyl-1-naphthol and steroidal thiazolidinone derivatives.
Ethyl bromoacetate finds applications in the preparation of reversibly photoresponsive coumarin-stabilized polymeric nanoparticles in an aqueous medium which act as a detectable drug carrier.
Chemical Properties
Ethyl bromoacetate is a clear, colorless to light-yellow liquid and has a pungent odor.
Ethyl bromoacetate is insoluble in water, but is soluble in acetone and benzene (Lide, 1999; Lewis, 1997).
Ethyl bromoacetate is miscible with ethanol, ethyl ether, and with other oxygenated and aromatic solvents (Ashford, 1994; Lide, 1999).
Ethyl bromoacetate is partially decomposed by water (Lewis, 1997).
Uses
Ethyl Bromoacetate, is used in the synthesis of metabolites of carcinogenic PAHs. Used in the preparation of steroidal antiestrogens through cyclic condensation. A reactant in the preparation of antim icrobial and antioxidant coumarinyloxymethyl-thiadiazolone.
General Description
A clear, colorless liquid (b.p. 318°F). Flash point 47°C. A lachrymator. Toxic by ingestion, inhalation and skin absorption; a strong irritant of the skin. Insoluble in water and soluble in alcohol, benzene, and ether. Specific gravity of 1.5.
Description
Colorless liquid with an unpleasant odor; [MSDSonline]
Sources/Uses
Used as a tear gas in the past; Also used as a warning odorant in toxic, odorless gases and to make pharmaceuticals and other chemicals;
Ethyl Bromoacetate-1,2-13C2-d2 is a labaled analog of Ethyl Bromoacetate (E900140) which, is used in the synthesis of metabolites of carcinogenic PAHs. Used in the preparation of steroidal antiestrogens through cyclic condensation. A reactant in the preparation of antimicrobial and antioxidant coumarinyloxymethyl-thiadiazolone.
About this substance
Helpful information
Ethyl Bromoacetate is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, for intermediate use only.
Ethyl Bromoacetate is used at industrial sites and in manufacturing.
Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Article service life
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the types of manufacture using this substance. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Formulation or re-packing
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Uses at industrial sites
ECHA has no public registered data indicating whether or in which chemical products the substance might be used.
Ethyl Bromoacetate is used in the following areas: scientific research and development.
Ethyl Bromoacetate is used for the manufacture of: chemicals.
Release to the environment of Ethyl Bromoacetate can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates).
Manufacture
Release to the environment of Ethyl Bromoacetate can occur from industrial use: manufacturing of the substance.
Ethyl Bromoacetate is the chemical compound with the formula CH2BrCO2C2H5.
Ethyl Bromoacetate is the ethyl ester of bromoacetic acid and is prepared in two steps from acetic 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.
Ethyl Bromoacetate 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.
In organic synthesis, Ethyl Bromoacetate is a versatile alkylating agent.
Ethyl Bromoacetates major application involves the Reformatskii reaction, wherein it reacts with zinc to form a zinc enolate. The resulting BrZnCH2CO2Et condenses with carbonyl compounds to give a β-hydroxy-esters.
Ethyl Bromoacetate is also the starting point for the preparation of several other reagents.
Ethyl Bromoacetate, is used in the synthesis of metabolites of carcinogenic PAHs. Used in the preparation of steroidal antiestrogens through cyclic condensation. A reactant in the preparation of antimicrobial and antioxidant coumarinyloxymethyl-thiadiazolone.
ProductType : Fine chemicals
Molecular Formula : C4H7BrO2
CASNo : 105-36-2
Grades : Technical Package
Molecular Weight : 167.00
Synonym : Bromoacetic acid ethyl ester,,,
Feature : Value :
Molecular Weight 195g
Boiling point (10 mmHg) 50°C
Flash point 49°C
Specific gravity at 25°C 1,321 g/cm3
Application
Ethyl bromoacetate was used to prepare reversibly photoresponsive coumarin-stabilized polymeric nanoparticles in an aqueous medium, which act as a detectable drug carrier.
General description
Ethyl bromoacetate on derivatisation reaction with p-t-butyl calix[4]arene yields 1,3-diester substituted calix[4]arene.
Ethyl bromoacetate also undergoes Suzuki type cross-coupling reactions with arylboronic acids cocatalyzed by copper(I) oxide.
IUPAC names
ethyl 2-bromoacetate
Ethyl Bromoacetate
Ethyl bromoacetate
ethyl bromoacetate
Ethylbromacetat
SYNONYMS:
105-36-2 [RN]
203-290-9 [EINECS]
Acetic acid, 2-bromo-, ethyl ester [ACD/Index Name]
Bromoacétate d'éthyle [French] [ACD/IUPAC Name]
Ethyl 2-Bromoacetate
Ethyl bromoacetate [ACD/IUPAC Name]
Ethyl α-bromoacetate
Ethyl-bromacetat [German] [ACD/IUPAC Name]
14341-47-0 [RN]
155388-71-9 [RN]
2-(3,3-dimethylbutylamino)-3,3-dimethylbutanoic acid methyl ester
222036-66-0 [RN]
2-bromoacetic acid ethyl ester
5-amino-2,3-dihydro-1H-isoindol-1-one
679806-14-5 [RN]
acetic acid, bromo-, ethyl ester
Acetic-1-13C acid,2-bromo-, ethyl ester (9CI)
Antol [Wiki]
bromoacetato de etila [Portuguese]
Bromoacetic acid ethyl ester
Bromo-acetic acid ethyl ester
Bromoacetic acid, ethyl ester
Ethoxycarbonylmethyl bromide
ETHYL 2 BROMOACETATE
ethyl 2-bromoethanoate
ethyl a-bromoacetate
Ethyl bromacetate
ETHYL BROMO ACETATE
Ethyl Bromoacetate-2,2-d2
Ethyl bromoacetic acid
Ethyl monobromoacetate
Ethyl α-bromoacetate
Ethyl?Bromoacetate
