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Xylenol

Xylenol

Overview
Xylenol or dimethylphenol is an arene compound with two methyl groups and a hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...

 group. 6 isomers exist of xylenol of which 2,6-xylenol with both methyl group in an ortho position
Arene substitution patterns
Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon.- Ortho, meta, and para substitution :...

 with respect to the hydroxyl group is the most important. The name xylenol is a portmanteau of the words xylene
Xylene
Xylene encompasses three isomers of dimethylbenzene. The isomers are distinguished by the designations ortho- , meta- , and para- , which specify to which carbon atoms the two methyl groups are attached...

 and phenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...

.


The physical properties of the 6 xylenol isomers are very similar.

Together with cresol
Cresol
Cresols are organic compounds which are methylphenols. They are a widely occurring natural and manufactured group of aromatic organic compounds which are categorized as phenols . Depending on the temperature, cresols can be solid or liquid because they have melting points not far from room...

s and cresylic acid, xylenols are an important class of phenolics with great industrial importance.
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Encyclopedia
Xylenol or dimethylphenol is an arene compound with two methyl groups and a hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...

 group. 6 isomers exist of xylenol of which 2,6-xylenol with both methyl group in an ortho position
Arene substitution patterns
Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon.- Ortho, meta, and para substitution :...

 with respect to the hydroxyl group is the most important. The name xylenol is a portmanteau of the words xylene
Xylene
Xylene encompasses three isomers of dimethylbenzene. The isomers are distinguished by the designations ortho- , meta- , and para- , which specify to which carbon atoms the two methyl groups are attached...

 and phenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...

.

Selected Properties


The physical properties of the 6 xylenol isomers are very similar.
Isomer 2,6-Xylenol
2,6-Xylenol
2,6-Xylenol is a chemical compound which is one of the six isomers of xylenol. It is also commonly known as 2,6-dimethylphenol .2,6-Xylenol is a monomer for poly engineering resins through carbon - oxygen oxidative coupling. Carbon to carbon dimerization is also possible...

2,5-Xylenol 2,4-Xylenol 2,3-Xylenol 3,4-Xylenol
3,4-Xylenol
3,4-Xylenol is a chemical compound which is one of the six isomers of xylenol....

3,5-Xylenol
CAS
CAS registry number
CAS Registry Numbersare unique numerical identifiers assigned by the "Chemical Abstracts Service" toevery chemical described in the...

576-26-1 95-87-4 105-67-9 526-75-0 95-65-8 108-68-9
Mp
Melting point
The melting point of a solid is the temperature at which it changes state from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium. The melting point of a substance depends on pressure and is usually specified at standard atmospheric pressure...

 °C
43-45 63 - 65 22-23 70-73 62 - 68 61-64
Bp
Boiling point
The boiling point of an element or a substance is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid....

 °C
203 212 211-212 217 227 222
Density
Density
The mass density or density of a material is defined as its mass per unit volume. The symbol most often used for density is ρ . In some cases , density is also defined as its weight per unit volume; although, this quantity is more properly called specific weight...

 g/mL
0.971 1.011

Uses


Together with cresol
Cresol
Cresols are organic compounds which are methylphenols. They are a widely occurring natural and manufactured group of aromatic organic compounds which are categorized as phenols . Depending on the temperature, cresols can be solid or liquid because they have melting points not far from room...

s and cresylic acid, xylenols are an important class of phenolics with great industrial importance. Xylenols are used as pesticide
Pesticide
Pesticides are substances or mixture of substances intended for preventing, destroying, repelling or mitigating any pest.A pesticide may be a chemical unicycle, biological agent , antimicrobial, disinfectant or device used against any pest...

s and used in the manufacture of antioxidant
Antioxidant
An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...

s. Xylenol orange
Xylenol orange
Xylenol orange is an organic reagent, most commonly used as a tetrasodium salt as an indicator for metal titrations. When used for metal titrations it will appear red in the titrand and yellow once it reaches its endpoint...

 is a redox indicator
Redox indicator
A redox indicator is an indicator that undergoes a definite color change at a specific electrode potential....

 built on a xylenol skeleton.

2,6-Xylenol is a monomer
Monomer
A monomer is an atom or a small molecule that may bind chemically to other monomers to form a polymer; the term "monomeric protein" may also be used to describe one of the proteins making up a multiprotein complex...

 for poly(p-phenylene oxide)
Poly(p-phenylene oxide)
Poly or poly is a high-temperature thermoplastic. It is rarely used in its pure form due to difficulties in processing. It is mainly used as blend with polystyrene, high impact styrene-butadiene copolymer or polyamide.-History:Polyphenylene ether was discovered in 1956 by A. S...

 engineering resins through carbon - oxygen oxidative coupling.

According to the 2000 United States Census, recreational use of xylenol is on the rise. Users report feelings of euphoria and auditory hallucinations.

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