Chloroacetaldehyde
Encyclopedia
Chloroacetaldehyde is the organic compound
with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous
form, but rather as the hydrate (acetal
), ClCH2CH(OH)2. Chloroacetaldehyde is a useful intermediate in the synthesis, e.g. of 2-aminothiazole or many pharmaceutical compounds.
Another use is to facilitate bark removal from tree trunks.
using chlorine
:
It can also be prepared from vinyl acetate
.
Being bifunctional, chloroacetaldehyde is a versatile precursor to many heterocyclic compound
s. It condenses with thiourea derivatives to give aminothiazole
s. This reaction was once important as a precursor to sulfathiazole
, one of the first sulfa drugs.
in the degradation of 1,2-dichloroethane
, which initially converts to chloroethanol. This metabolic pathway is topical since billions of kilograms of 1,2-dichloroethane have been produced as a precursor to vinyl chloride
.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous
Anhydrous
As a general term, a substance is said to be anhydrous if it contains no water. The way of achieving the anhydrous form differs from one substance to another...
form, but rather as the hydrate (acetal
Acetal
An acetal is a molecule with two single-bonded oxygen atoms attached to the same carbon atom.Traditional usages distinguish ketals from acetals...
), ClCH2CH(OH)2. Chloroacetaldehyde is a useful intermediate in the synthesis, e.g. of 2-aminothiazole or many pharmaceutical compounds.
Another use is to facilitate bark removal from tree trunks.
Synthesis and reactions
The hydrate of chloroacetaldehyde is produced by the oxidation of aqueous vinyl chlorideVinyl chloride
Vinyl chloride is the organochloride with the formula H2C:CHCl. It is also called vinyl chloride monomer, VCM or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride . At ambient pressure and temperature, vinyl chloride...
using chlorine
Chlorine
Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine...
:
- ClCH=CH2 + Cl2 + H2O → ClCH2CHO + 2 HCl
It can also be prepared from vinyl acetate
Vinyl acetate
Vinyl acetate is an organic compound with the formula CH3COOCH=CH2. A colorless liquid with a pungent odor, it is the precursor to polyvinyl acetate, an important polymer in industry.-Production:...
.
Being bifunctional, chloroacetaldehyde is a versatile precursor to many heterocyclic compound
Heterocyclic compound
A heterocyclic compound is a cyclic compound which has atoms of at least two different elements as members of its ring. The counterparts of heterocyclic compounds are homocyclic compounds, the rings of which are made of a single element....
s. It condenses with thiourea derivatives to give aminothiazole
Aminothiazole
2-Aminothiazole is a heterocyclic amine with odor similar to pyridine, soluble in water, alcohol and ether. It is a beginning point for synthesis of many compounds including sulfur drugs, biocides, fungicides, dyes and chemical reaction accelerators. 2-Aminothiazole can be used as a thyroid...
s. This reaction was once important as a precursor to sulfathiazole
Sulfathiazole
Sulfathiazole is an organosulfur compound that has been used as a short-acting sulfa drug. It once was a common oral and topical antimicrobial until less toxic alternatives were discovered. It is still occasionally used, sometimes in combination with sulfabenzamide and sulfacetamide, and in...
, one of the first sulfa drugs.
Environmental aspects
Chloroacetaldehyde is a metaboliteMetabolite
Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction. Alcohol is an example of a primary metabolite produced in large-scale by industrial...
in the degradation of 1,2-dichloroethane
1,2-Dichloroethane
The chemical compound 1,2-dichloroethane, commonly known by its old name of ethylene dichloride , is a chlorinated hydrocarbon, mainly used to produce vinyl chloride monomer , the major precursor for PVC production. It is a colourless liquid with a chloroform-like odour...
, which initially converts to chloroethanol. This metabolic pathway is topical since billions of kilograms of 1,2-dichloroethane have been produced as a precursor to vinyl chloride
Vinyl chloride
Vinyl chloride is the organochloride with the formula H2C:CHCl. It is also called vinyl chloride monomer, VCM or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride . At ambient pressure and temperature, vinyl chloride...
.