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Ethyl bromoacetate

 

 
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Ethyl bromoacetate
 
 
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Ethyl 2-bromoacetate is the chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
 with the formula CH2BrCO2C2H5. It is the ethyl
Ethyl group

In chemistry, an ethyl group is an alkyl functional group derived from ethane . It has the chemical formula -Carbon2Hydrogen5 and is very often abbreviated -Et....
 ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
 of bromoacetic acid
Bromoacetic acid

Bromoacetic acid is the chemical compound with the chemical formula CH2BrCO2H. This colorless solid is a relatively strong alkylating agent....
 and is prepared in two steps from acetic acid
Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
.

a class="link1" onMouseover='showByLink("m5016021",this)' onMouseout='hide("m5016021")'href="http://www.absoluteastronomy.com/topics/World_War_I">World War I
World War I

World War I, or the First World War , was a global military conflict which involved the Great powers, organized into two opposing military alliances: the Allies of World War I and the Central Powers....
, ethyl bromoacetate was used as a lachrymatory agent
Lachrymatory agent

A lachrymatory agent or lachrymator is a chemical compound that stimulates the corneal nerves in the eyes to cause tears, pain, and even temporary blindness....
 and tear gas agent for chemical warfare
Chemical warfare

Chemical warfare involves using the poison of chemical substances as weapons to kill, injure, or incapacitate an Enemy .This type of warfare is distinct from the use of conventional weapons or nuclear weapons because the destructive effects of chemical weapons are not primarily due to their explosion force....
 under the German code Weisskreuz
White Cross (chemical warfare)

White Cross is a World War I chemical warfare agent consisting of one or more lachrymatory agents: bromoacetone , bromobenzyl cyanide , bromomethyl ethyl ketone , chloroacetone , ethyl bromoacetate, and/or xylyl bromide....
 (White Cross), and later as odorant or warning agent in odourless, toxic gases.






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Encyclopedia


Ethyl 2-bromoacetate is the chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
 with the formula CH2BrCO2C2H5. It is the ethyl
Ethyl group

In chemistry, an ethyl group is an alkyl functional group derived from ethane . It has the chemical formula -Carbon2Hydrogen5 and is very often abbreviated -Et....
 ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
 of bromoacetic acid
Bromoacetic acid

Bromoacetic acid is the chemical compound with the chemical formula CH2BrCO2H. This colorless solid is a relatively strong alkylating agent....
 and is prepared in two steps from acetic acid
Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
.

Applications

In World War I
World War I

World War I, or the First World War , was a global military conflict which involved the Great powers, organized into two opposing military alliances: the Allies of World War I and the Central Powers....
, ethyl bromoacetate was used as a lachrymatory agent
Lachrymatory agent

A lachrymatory agent or lachrymator is a chemical compound that stimulates the corneal nerves in the eyes to cause tears, pain, and even temporary blindness....
 and tear gas agent for chemical warfare
Chemical warfare

Chemical warfare involves using the poison of chemical substances as weapons to kill, injure, or incapacitate an Enemy .This type of warfare is distinct from the use of conventional weapons or nuclear weapons because the destructive effects of chemical weapons are not primarily due to their explosion force....
 under the German code Weisskreuz
White Cross (chemical warfare)

White Cross is a World War I chemical warfare agent consisting of one or more lachrymatory agents: bromoacetone , bromobenzyl cyanide , bromomethyl ethyl ketone , chloroacetone , ethyl bromoacetate, and/or xylyl bromide....
 (White Cross), and later as odorant or warning agent in odourless, toxic gases. It is listed by the WHO
Who

*Who is an English language interrogative pronoun....
 as a riot control agent
Riot control agent

Riot control agents are less-lethal lachrymatory agents used for riot control. Most commonly used riot control agents are pepper spray and various kinds of tear gas....
, 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
World War I

World War I, or the First World War , was a global military conflict which involved the Great powers, organized into two opposing military alliances: the Allies of World War I and the Central Powers....
. The German army then used this attack to justify their subsequent employment of chemical weapons in 1915.

In organic synthesis
Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
, it is a versatile alkylating agent. Its major application involves the Reformatsky reaction, wherein it reacts with zinc
Zinc

Zinc is a metallic chemical element with the symbol Zn and atomic number 30. It is a first-row transition metal of the group 12 element of the periodic table....
 to form a zinc enolate. The resulting BrZnCH2CO2Et condenses with carbonyl
Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
 compounds to give a ß-hydroxy-esters.

It is also the starting point for the preparation of several other reagents. For example, the related Wittig reagent
Wittig reaction

The Wittig reaction is a chemical reaction of an aldehyde or ketone with a triphenyl #Wittig reagents to give an alkene and triphenylphosphine oxide....
 (prepared by reaction with triphenylphosphine
Triphenylphosphine

Triphenylphosphine is a common organophosphorus compound with the formula P3 - often abbreviated to PhosphorusPhenyl group or Ph3P....
) is commonly used to prepare alpha,beta-unsaturated
Unsaturated compound

In organic chemistry, an unsaturated compound is a chemical compound that contains carbon-carbon double bonds or triple bonds such as in alkenes or alkynes....
 ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
s from carbonyl compounds such as benzaldehyde
Benzaldehyde

Benzaldehyde is a chemical compound consisting of a benzene ring with an aldehyde substituent. It is the simplest representative of the aromatic aldehydes and one of the most industrially used members of this family of compounds....
:

Esterstabilisedwittigscheme