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Chlorobenzene

 

 
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Chlorobenzene
 
 
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Chlorobenzene is an aromatic organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the chemical formula C6H5Cl. This a colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.

robenzene once was used in the manufacture of certain pesticide
Pesticide

A pesticide is a substance or mixture of substances used to kill a pest .A pesticide may be a chemical substance, biological agent , antimicrobial, disinfectant or device used against any pest ....
s, most notably DDT
DDT

DDT is one of the best known synthetic pesticides. It is a chemical with a long, unique, and controversial history.First synthesized in 1874, DDT's insecticidal properties were not discovered until 1939....
 by reaction with chloral
Chloral

Chloral, also known as trichloroacetaldehyde, is the organic compound with the formula Cl3CCHO. This aldehyde is a colourless oily liquid that is soluble in a wide range of solvents....
 (trichloroacetaldehyde), but this application has declined with the diminished use of DDT.






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Encyclopedia


Chlorobenzene is an aromatic organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the chemical formula C6H5Cl. This a colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.

Uses

Chlorobenzene once was used in the manufacture of certain pesticide
Pesticide

A pesticide is a substance or mixture of substances used to kill a pest .A pesticide may be a chemical substance, biological agent , antimicrobial, disinfectant or device used against any pest ....
s, most notably DDT
DDT

DDT is one of the best known synthetic pesticides. It is a chemical with a long, unique, and controversial history.First synthesized in 1874, DDT's insecticidal properties were not discovered until 1939....
 by reaction with chloral
Chloral

Chloral, also known as trichloroacetaldehyde, is the organic compound with the formula Cl3CCHO. This aldehyde is a colourless oily liquid that is soluble in a wide range of solvents....
 (trichloroacetaldehyde), but this application has declined with the diminished use of DDT. At one time, chlorobenzene was the main precursor for the manufacture of phenol
Phenol

Phenol, also known as carbolic acid, is a toxic, white crystalline solid with a sweet tarry odor, commonly referred to as a "hospital smell"....
:
C6H5Cl + NaOH ? C6H5OH + NaCl
As of 2005, the major use of chlorobenzene is as an intermediate in the production of commodities such as herbicides, dyestuffs, and rubber. Chlorobenzene is also used as a high-boiling solvent
Solvent

A solvent is a liquid or gas that dissolves a solid, liquid, or gaseous solute, resulting in a solution.The most common solvent in everyday life is water....
 in many industrial applications as well as in the laboratory. More specifically, the chlorobenzene is nitrated on a large scale to give nitrochlorobenzene, which is converted to related phenol, anisole, and aniline derivatives.

Synthesis

Chlorobenzene was first described in 1851, when it was prepared by reacting phenol
Phenol

Phenol, also known as carbolic acid, is a toxic, white crystalline solid with a sweet tarry odor, commonly referred to as a "hospital smell"....
 and phosphorus pentachloride. Presently it is manufactured by chlorination
Electrophilic halogenation

In organic chemistry, an electrophilic aromatic halogenation is a type of electrophilic aromatic substitution. This organic reaction is typical of aromatic compounds and a very useful method for adding substituents to an aromatic system....
 of benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
 in the presence of a catalytic amount of Lewis acid
Lewis acid

A Lewis acid is a chemical compound, A, that can accept a pair of electrons from a Lewis base, B, that acts as an electron-pair donor, forming an adduct, AB.Gilbert N....
 such as ferric chloride:
The catalyst enhances the electrophilicity of the chlorine. Because chlorine is electronegative, C6H5Cl exhibits decreased susceptibility to attack by other electrophiles. For this reason, the chlorination process produces only small amounts of dichloro- and trichlorobenzenes.

Safety

Chlorobenzene exhibits "low to moderate" toxicity as indicated by its LD50
LD50

In toxicology, the median lethal dose, LD50 , or LCt50 of a toxic substance or radiation is the Dose required to kill half the members of a tested population....
 of 2.9 g/kg.