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Benzyl alcohol is an 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 formula C6H5CH2OH. The benzyl
Benzyl

In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C6H5CH2-....
 group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is a useful solvent due to its polarity, low toxicity, and low vapor pressure
Vapor pressure

Vapor pressure , is the pressure of a vapor in Thermodynamic equilibrium with its non-vapor Phase s. All liquids and solids have a tendency to evaporate to a gaseous form, and all gases have a tendency to Condensation back into their original form ....
. Benzyl alcohol is partially soluble in water
Water

Water is a common chemical substance that is essential for the survival of all known forms of life. In typical usage, water refers only to its liquid form or States of matter, but the substance also has a solid state, ice, and a gaseous state, water vapor or steam....
 (4 g/100 mL) and completely miscible in alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s and ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
.






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Benzyl alcohol is an 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 formula C6H5CH2OH. The benzyl
Benzyl

In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C6H5CH2-....
 group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is a useful solvent due to its polarity, low toxicity, and low vapor pressure
Vapor pressure

Vapor pressure , is the pressure of a vapor in Thermodynamic equilibrium with its non-vapor Phase s. All liquids and solids have a tendency to evaporate to a gaseous form, and all gases have a tendency to Condensation back into their original form ....
. Benzyl alcohol is partially soluble in water
Water

Water is a common chemical substance that is essential for the survival of all known forms of life. In typical usage, water refers only to its liquid form or States of matter, but the substance also has a solid state, ice, and a gaseous state, water vapor or steam....
 (4 g/100 mL) and completely miscible in alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s and ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
. It is prepared by the hydrolysis
Hydrolysis

Hydrolysis is a chemical reaction during which one or more water are split into hydrogen and hydroxide ions which may go on to participate in further reactions....
 of benzyl chloride
Benzyl chloride

Benzyl chloride, or a-chlorotoluene, is an organic compound consisting of a phenyl substituted with a chloromethyl group....
 using sodium hydroxide
Sodium hydroxide

Sodium hydroxide , also known as lye, caustic soda and sodium hydrate, is a caustic metallic Base . Sodium hydroxide forms a strong alkaline solution when dissolved in a solvent such as water, however, only the hydroxide ion is basic....
:
C6H5CH2Cl + NaOH
Sodium hydroxide

Sodium hydroxide , also known as lye, caustic soda and sodium hydrate, is a caustic metallic Base . Sodium hydroxide forms a strong alkaline solution when dissolved in a solvent such as water, however, only the hydroxide ion is basic....
  → C6H5CH2OH + NaCl
Sodium chloride

Sodium chloride, also known as common salt, table salt, or halite, is a chemical compound with the chemical formula SodiumChlorine....
It can also be prepared via a Grignard reaction
Grignard reaction

The Grignard reaction, named after the French chemist Fran?ois Auguste Victor Grignard, is an organometallic chemistry chemical reaction in which alkyl- or aryl-magnesium halides , act as nucleophiles, attack electrophilic carbon atoms that are present within polar bonds to yield a carbon-carbon bond , thus altering hybridization about the r...
 by reacting phenylmagnesium bromide
Phenylmagnesium bromide

Phenylmagnesium bromide, with the simplified formula C6H5MgBr, is a magnesium-containing organometallic compound. It is so commonly used that it is commercially available as a solution in diethyl ether or tetrahydrofuran ....
 (C6H5MgBr) with formaldehyde
Formaldehyde

Formaldehyde is a chemical compound with the chemical formula H2CO. It is the simplest aldehyde. Formaldehyde exists in several forms aside from H2CO: the cyclic trimer trioxane and the polymer Polyoxymethylene....
, followed by acidification. Like most alcohols, it reacts with carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
s to form ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
s. Benzyl alcohol is produced naturally by many plants and is commonly found in fruits and teas. It is also found in a variety of essential oil
Essential oil

An essential oil is a concentrated, hydrophobic liquid containing volatile aroma compounds from plants. They are also known as volatile or ethereal oils, or simply as the "oil of" the plant material from which they were extracted, such as oil of clove....
s including jasmine
Jasmine

Jasmine is a genus of shrubs and vines in the olive family ,with about 200 species, native to tropical and warm temperate regions of the Old World....
, hyacinth, and ylang-ylang
Ylang-ylang

Ylang-ylang Cananga odorata, is a small flower of the cananga tree. It is a fast-growing tree that exceeds 5 meters per year and attains an average height of 12 meters....
.

Applications

Benzyl alcohol is used as a general 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....
 for ink
Ink

An ink is a liquid containing various pigments and/or dyes used for coloring a surface to produce an , writing, or design. Ink is used for drawing and/or writing with a pen, brush or quill....
s, paint
Paint

Paint is any liquid, liquifiable, or mastic composition which after application to a Substrate in a thin layer is converted to an opaque solid film....
s, lacquer
Lacquer

In a general sense, lacquer is a clear or coloured varnish that dries by solvent evaporation and often a curing process as well that produces a hard, durable finish, in any sheen level from ultra matte to high Gloss and that can be further polished as required....
s, and epoxy resin coatings. It is also a precursor to a variety of esters, used in the soap
SOAP

SOAP, originally defined as Simple Object Access Protocol, is a protocol specification for exchanging structured information in the implementation of Web Services in computer networks....
, 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....
, and flavor industries. It is often added to intravenous medication solutions as a preservative due to its bacteriostatic and antipruritic
Antipruritic

Antipruritics, also known as anti-itch drugs, are medications that inhibit the itching that is often associated with sunburns, allergic reactions, eczema, psoriasis, chickenpox, fungal infections, insect bites and stings like those from mosquitoes, fleas, and mites, and contact dermatitis and urticaria caused by plants such as poison i...
 properties. It is also used as a photographic developer.

Illustrative organic synthetic uses


In organic synthesis, benzyl esters are popular 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....
s because they can be removed by mild hydrogenolysis
Hydrogenolysis

Hydrogenolysis is a chemical reaction whereby a carbon-carbon or carbon-heteroatom single bond is cleaved or undergoes "lysis" by hydrogen. The heteroatom may vary, but it usually is oxygen, nitrogen, or sulfur....
.

BnOH reacts with acrylonitrile
Acrylonitrile

Acrylonitrile is the chemical compound with the formula CH2CHCN. This pungent-smelling colorless liquid often appears yellow due to impurities....
 to give N-benzylacrylamide. This is an example of a Ritter reaction
Ritter reaction

The Ritter reaction is a chemical reaction that transforms a nitrile into a N-alkyl amide using various alkylating reagents, for example, strong acid and isobutylene....
:
C6H5CH2OH + NCCHCH2 → C6H5CH2N(H)C(O)CHCH2


Nanotechnological uses


Benzyl alcohol has been used as a dielectric solvent for the dielectrophoretic
Dielectrophoresis

Dielectrophoresis is a phenomenon in which a force is exerted on a dielectric particle when it is subjected to a non-uniform electric field. This force does not require the particle to be electric charge....
 reconfiguration of nanowires.

Use in Health Care


Benzyl alcohol is used as a bacteriostatic preservative at low concentration in intravenous medications. It is oxidized rapidly in healthy individuals to benzoic acid, conjugated with glycine in the liver, and excreted as hippuric acid. High concentrations can result in toxic effects including respiratory failure, vasodilation, hypotension, convulsions, and paralysis. Newborns, especially if critically ill, may not metabolize benzyl alcohol as readily as adults. Reports in the early 1980s of sixteen neonatal deaths associated with the use of saline flush solutions containing benzyl alcohol preservative led to recommendations to avoid its use in neonates.

Other uses


Benzyl alcohol has nearly the same refraction index of quartz
Quartz

Quartz is the most abundant mineral in the Earth's continental crust . It is made up of a Crystal structure of silica tetrahedra. Quartz has a hardness of 7 on the Mohs scale and a density of 2.65 g/cm?....
 and wool fibre. If a clear quartz object is immersed in benzyl alcohol, it becomes almost invisible. This has been used as a method to non-destructively recognize if an object is made of true quartz or not (see Crystal skulls). Similarly, white wool immersed in benzyl alcohol also becomes almost invisible clearly revealing contaminants such as dark & medullated fibres and vegetable matter.