Suvarna Garge (Editor)

Benzyl alcohol

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Appearance
  
Colorless liquid

Density
  
1.04 g/cm³

Molar mass
  
108.14 g/mol

Melting point
  
-15 °C

Formula
  
C7H8O

Boiling point
  
205 °C

IUPAC ID
  
Phenylmethanol

Soluble in
  
Water

Benzyl alcohol FileBenzylalcohol2Dskeletalpng Wikimedia Commons

Water and benzyl alcohol


Benzyl alcohol is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), 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. Benzyl alcohol has moderate solubility in water (4 g/100 mL) and miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.

Contents

Benzyl alcohol Benzyl alcohol anhydrous 998 C6H5CH2OH SigmaAldrich

Natural occurrences

Benzyl alcohol Benzyl Alcohol Manufacturers Suppliers amp Exporters of Benzyl Alcohols

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 oils including jasmine, hyacinth, and ylang-ylang.

It is also one of the chemical compounds found in castoreum from the castor sacs of beavers.

Preparation

Benzyl alcohol is prepared by the hydrolysis of benzyl chloride using sodium hydroxide:

C6H5CH2Cl + NaOH → C6H5CH2OH + NaCl
Benzyl alcohol benzyl alcohol C7H8O ChemSpider

It can also be prepared via a Grignard reaction by reacting phenylmagnesium bromide (C6H5MgBr) with formaldehyde, followed by acidification.

Reactions

Benzyl alcohol Benzyl alcohol for analysis ACROS OrganicsChemicalsOther

Like most alcohols, it reacts with carboxylic acids to form esters. In organic synthesis, benzyl esters are popular protecting groups because they can be removed by mild hydrogenolysis.

Benzyl alcohol reacts with acrylonitrile to give N-benzylacrylamide. This is an example of a Ritter reaction:

C6H5CH2OH + NCCHCH2 → C6H5CH2N(H)C(O)CHCH2

Applications

Benzyl alcohol bmse010136 4Methoxy benzyl alcohol at BMRB

Benzyl alcohol is used as a general solvent for inks, waxes, shellacs, paints, lacquers, and epoxy resin coatings. Thus it can be used in paint strippers, especially when combined with compatible viscosity enhancers to encourage the mixture to cling to painted surfaces. It is a precursor to a variety of esters, used in the soap, perfume, and flavor industries. It is also used in e-liquid for e-cigarettes to enhance the flavors used. When applied to damaged skin or mucous membranes at a 10% concentration it acts as a local anesthetic and antimicrobial agent, and is sometimes included as a degreaser in rug cleaning products. As a dye solvent, it enhances the process of dying wool, nylon, and leather. It also has use as a photographic developer, and as an insect repellent.

Nanotechnological uses

Benzyl alcohol has been used as a dielectric solvent for the dielectrophoretic reconfiguration of nanowires.

Use in health care

Benzyl alcohol is used as a bacteriostatic preservative at low concentration in intravenous medications, cosmetics and topical drugs.

Benzyl alcohol Benzyl alcohol C7H8O ChemSynthesis

The use of benzyl alcohol as a 5% solution has been approved by the U.S. FDA for the treatment of head lice in children older than 6 months and in adults. It affects the louse's spiracles, preventing them from closing. These then become clogged with water or mineral oil or other matter and cause the insect to die from asphyxiation.

Other uses

Benzyl alcohol Benzyl Alcohol View Latest Price amp Details in Shradanand Building

Benzyl alcohol has nearly the same refraction index as quartz and wool fiber. If a clear quartz object is immersed in benzyl alcohol, it becomes almost invisible. This test has been used to determine non-destructively whether an object is truly made of quartz (see crystal skull). Similarly, white wool immersed in benzyl alcohol also becomes almost invisible clearly revealing contaminants such as dark and medullated fibers and vegetable matter. Benzyl alcohol is used effectively for treating lice infestations as the active ingredient in lotion shampoo with 5% benzyl alcohol.

Safety

Benzyl alcohol Benzyl Alcohol Allergy Importance of Patch Testing

Benzyl alcohol has low acute toxicity with an LD50 of 1.2 g/kg in rats. It oxidizes rapidly in healthy individuals to benzoic acid, conjugated with glycine in the liver, and excreted as hippuric acid. Very high concentrations can result in toxic effects including respiratory failure, vasodilation, hypotension, convulsions, and paralysis.

Benzyl alcohol is toxic to neonates, it is associated with the gasping syndrome.

Benzyl alcohol has been reported to cause skin allergy.

Benzyl alcohol is severely toxic and highly irritating to the eye. Pure benzyl alcohol produces corneal necrosis.

Benzyl alcohol Metaphenoxy Benzyl Alcohol Metaphenoxy Benzyl Alcohol Exporter

Benzyl alcohol is not considered to be a carcinogen and no data are available regarding teratogenic or reproductive effects.

References

Benzyl alcohol Wikipedia


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