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Anisole

 

 
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Anisole
 
 
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Anisole, also known as methoxybenzene, is a color
Color

Color or colour is the visual perception property corresponding in humans to the categories called red, yellow, blue and others....
less liquid
Liquid

Liquid is one of the principal states of matter. A liquid is a fluid that has the particles loose and can freely form a distinct surface at the boundaries of its bulk material....
 with a smell
Odor

An odor or odour is a volatilized chemical compound, generally at a very low concentration, that humans or other animals perceive by the sense of olfaction....
 similar to that of anise
Anise

is a flowering plant in the family Apiaceae native to the eastern Mediterranean region and southwest Asia known for its flavor that resembles licorice, fennel, and tarragon....
 seed, and can be quite nauseating.

ole is more electron
Electron

The electron is a subatomic particle that carries a negative electric charge. It has elementary particle and is believed to be a point particle....
 rich than benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
 because of the resonance effect of the methoxy
Methoxy

In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. It has the formula:The word is used in organic nomenclature usually to describe an ether....
 group upon the aromatic ring. This resonance effect has a greater effect upon the pi cloud of the ring than the inductive effect
Inductive effect

The inductive effect in chemistry is an experimentally observable effect of the transmission of charge through a chain of atoms in a molecule by electrostatic induction....
 where the electronegative oxygen
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
 exerts a pull on the electron density in the benzene ring through the sigma bond
Sigma bond

In chemistry, sigma bonds are the strongest type of covalent bond chemical bond. Sigma bonding is most clearly defined for diatomic molecules using the language and tools of symmetry groups....
.

Anisole reacts with electrophile
Electrophile

In chemistry, an electrophile is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to Chemical bond to a nucleophile....
s in the electrophilic aromatic substitution
Electrophilic aromatic substitution

Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic ring is replaced by an electrophile....
 reaction more quickly than benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
, which in turn reacts more quickly than nitrobenzene
Nitrobenzene

Nitrobenzene, also known as nitrobenzol or oil of mirbane, is an organic compound with the chemical formula Carbon6Hydrogen5NitrogenOxygen2....
.

Rate of reaction:
Anisole > Benzene > Nitrobenzene


The methoxy group acts as an ortho
Ortho

Ortho may refer to:In science* An arene substitution patterns in which two substituents occupy adjacent positions on an aromatic ring...
/para
Pará

Par? is one of the States of Brazil of Brazil, located in the northern part of the country.Neighboring states are Amap?, Maranh?o, Tocantins , Mato Grosso, Amazonas, Brazil and Roraima....
 directing group.

ole may be prepared by the Williamson ether synthesis
Williamson ether synthesis

The Williamson ether synthesis is an organic reaction, forming an ether from a organohalide and an alcohol. This reaction was developed by Alexander William Williamson in 1850 ....
, reacting sodium phenoxide with dimethyl sulfate
Dimethyl sulfate

Dimethyl sulfate is a chemical compound with chemical formula 2SO2. As the dimethyl ester of sulfuric acid, its formula is often written as 2Sulfate or even Me2SO4, where CH3 or Me is methyl....
:

2 PhO−Na+ + Me2SO4 → 2 PhOMe + Na2SO4


ole is used in perfume
Perfume

Perfume is a mixture of fragrant essential oils and aroma compounds, fixatives, and solvents used to give the human body, animals, objects, and living spaces a pleasant smell....
ry and chemical syntheses
Chemical synthesis

In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product , or several products. This happens by physics and chemical manipulations usually involving one or more reactions....
, and is an insect
Insect

Insects are the biggest class of arthropods and the only ones with wings. They are the most diverse group of animals on the planet. They are most diverse at the equator and their diversity declines toward the poles....
 pheromone
Pheromone

A pheromone is a chemical that triggers a natural behavioral response in another member of the opposite gender of the same species. There are alarm signal pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology....
.

Anisole reacts with acetic anhydride
Acetic anhydride

Acetic anhydride is the chemical compound with the chemical formula 2O. Commonly abbreviated Acetyl2O, it is one of the simplest acid anhydrides and is a widely used reagent in organic synthesis....
 to give 4-methoxyacetophenone and 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....
 as a byproduct.






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Encyclopedia


Anisole, also known as methoxybenzene, is a color
Color

Color or colour is the visual perception property corresponding in humans to the categories called red, yellow, blue and others....
less liquid
Liquid

Liquid is one of the principal states of matter. A liquid is a fluid that has the particles loose and can freely form a distinct surface at the boundaries of its bulk material....
 with a smell
Odor

An odor or odour is a volatilized chemical compound, generally at a very low concentration, that humans or other animals perceive by the sense of olfaction....
 similar to that of anise
Anise

is a flowering plant in the family Apiaceae native to the eastern Mediterranean region and southwest Asia known for its flavor that resembles licorice, fennel, and tarragon....
 seed, and can be quite nauseating.

Structure and properties

Anisole is more electron
Electron

The electron is a subatomic particle that carries a negative electric charge. It has elementary particle and is believed to be a point particle....
 rich than benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
 because of the resonance effect of the methoxy
Methoxy

In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. It has the formula:The word is used in organic nomenclature usually to describe an ether....
 group upon the aromatic ring. This resonance effect has a greater effect upon the pi cloud of the ring than the inductive effect
Inductive effect

The inductive effect in chemistry is an experimentally observable effect of the transmission of charge through a chain of atoms in a molecule by electrostatic induction....
 where the electronegative oxygen
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
 exerts a pull on the electron density in the benzene ring through the sigma bond
Sigma bond

In chemistry, sigma bonds are the strongest type of covalent bond chemical bond. Sigma bonding is most clearly defined for diatomic molecules using the language and tools of symmetry groups....
.

Anisole reacts with electrophile
Electrophile

In chemistry, an electrophile is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to Chemical bond to a nucleophile....
s in the electrophilic aromatic substitution
Electrophilic aromatic substitution

Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic ring is replaced by an electrophile....
 reaction more quickly than benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
, which in turn reacts more quickly than nitrobenzene
Nitrobenzene

Nitrobenzene, also known as nitrobenzol or oil of mirbane, is an organic compound with the chemical formula Carbon6Hydrogen5NitrogenOxygen2....
.

Rate of reaction:
Anisole > Benzene > Nitrobenzene


The methoxy group acts as an ortho
Ortho

Ortho may refer to:In science* An arene substitution patterns in which two substituents occupy adjacent positions on an aromatic ring...
/para
Pará

Par? is one of the States of Brazil of Brazil, located in the northern part of the country.Neighboring states are Amap?, Maranh?o, Tocantins , Mato Grosso, Amazonas, Brazil and Roraima....
 directing group.

Preparation

Anisole may be prepared by the Williamson ether synthesis
Williamson ether synthesis

The Williamson ether synthesis is an organic reaction, forming an ether from a organohalide and an alcohol. This reaction was developed by Alexander William Williamson in 1850 ....
, reacting sodium phenoxide with dimethyl sulfate
Dimethyl sulfate

Dimethyl sulfate is a chemical compound with chemical formula 2SO2. As the dimethyl ester of sulfuric acid, its formula is often written as 2Sulfate or even Me2SO4, where CH3 or Me is methyl....
:

2 PhO−Na+ + Me2SO4 → 2 PhOMe + Na2SO4


Applications

Anisole is used in perfume
Perfume

Perfume is a mixture of fragrant essential oils and aroma compounds, fixatives, and solvents used to give the human body, animals, objects, and living spaces a pleasant smell....
ry and chemical syntheses
Chemical synthesis

In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product , or several products. This happens by physics and chemical manipulations usually involving one or more reactions....
, and is an insect
Insect

Insects are the biggest class of arthropods and the only ones with wings. They are the most diverse group of animals on the planet. They are most diverse at the equator and their diversity declines toward the poles....
 pheromone
Pheromone

A pheromone is a chemical that triggers a natural behavioral response in another member of the opposite gender of the same species. There are alarm signal pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology....
.

Anisole reacts with acetic anhydride
Acetic anhydride

Acetic anhydride is the chemical compound with the chemical formula 2O. Commonly abbreviated Acetyl2O, it is one of the simplest acid anhydrides and is a widely used reagent in organic synthesis....
 to give 4-methoxyacetophenone and 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....
 as a byproduct. The reaction of anisole with P4S10 forms Lawesson's reagent
Lawesson's reagent

Lawesson's reagent, or LR, is a chemical compound used in organic synthesis as a thiation agent. Lawesson's reagent was first made popular by Sven-Olov Lawesson, who did not, however, invent it....
 an important chemical in phosphorus
Phosphorus

Phosphorus is the chemical element that has the symbol P and atomic number 15. The name comes from the and . A Valency nonmetal of the nitrogen group, phosphorus is commonly found in inorganic phosphate minerals....
-sulfur
Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
 chemistry.

See also

  • Anethole
    Anethole

    Anethole is an aromatic compound that occurs widely in nature, in essential oils. It contributes a large component of the distinctive flavors of anise and fennel , Syzygium anisatum , licorice , and star anise ....
  • Bromoanisole
    Bromoanisole

    Bromoanisole, also known as para-bromoanisole or 1-bromo-4-methoxybenzene, is a clear liquid with a pleasant odor similar to that of anise seed....
  • Butylated hydroxyanisole
    Butylated hydroxyanisole

    E320 redirects here. For the automobile, see Mercedes-Benz E-Class.Butylated hydroxyanisole is an antioxidant consisting of a mixture of two isomeric organic compounds, 2-tert-butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole....
  • Ether
    Ether

    Ether is a class of organic compounds which contain an ether functional group ? an oxygen atom connected to two alkyl or aryl groups ? of general formula R?O?R....
  • Ethyl phenyl ether
    Ethyl phenyl ether

    Ethyl phenyl ether or phenetole is an organic compound that is an ether. Ethyl phenyl ether has the same properties as some other ethers, such as volatility, explosive vapors, and the ability to form peroxides....
  • 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"....
  • 2,4,6-Trichloroanisole (cork taint)


External links

  • pheromone database entry