Chloroformate
Encyclopedia
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
s of chloroformic acid
Chloroformic acid
Chloroformic acid is an unstable chemical compound with the formula ClCO2H. It is the single acyl-halide derivative of carbonic acid . Chloroformic acid is also structurally related to formic acid, which has a hydrogen instead of the chlorine...
. They are widely used as reagent
Reagent
A reagent is a "substance or compound that is added to a system in order to bring about a chemical reaction, or added to see if a reaction occurs." Although the terms reactant and reagent are often used interchangeably, a reactant is less specifically a "substance that is consumed in the course of...
s in organic chemistry. For example, benzyl chloroformate
Benzyl chloroformate
Benzyl chloroformate is the benzyl ester of chloroformic acid. It is also known as benzyl chlorocarbonate is an oily liquid whose color is anywhere from yellow to colorless. It is also known for its pungent odor...
is used to introduce the CBZ
Carboxybenzyl
Carboxybenzyl or Cbz or Z is an amine protecting group in organic synthesis. It is commonly used in peptide synthesis and is formed by reacting an amine with benzyl chloroformate and a weak base:It is used to protect amines from electrophiles...
protecting group
Protecting group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction...
and fluorenylmethyloxycarbonylchloride is used to introduce the FMOC protecting group.
Reactions
Chloroformates have similar reactivity to other acyl chlorideAcyl chloride
In organic chemistry, an acyl chloride is an organic compound with the functional group -CO-Cl. Their formula is usually written RCOCl, where R is a side chain. They are usually considered to be reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride,...
s, such as:
- Reaction with amineAmineAmines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
s to form carbamateCarbamateCarbamates are organic compounds derived from carbamic acid . A carbamate group, carbamate ester, and carbamic acids are functional groups that are inter-related structurally and often are interconverted chemically. Carbamate esters are also called urethanes.-Synthesis:Carbamic acids are derived...
s - Reaction with alcoholAlcoholIn chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....
s to form carbonateCarbonateIn chemistry, a carbonate is a salt of carbonic acid, characterized by the presence of the carbonate ion, . The name may also mean an ester of carbonic acid, an organic compound containing the carbonate group C2....
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