Benzyl Alcohol (C6H5CH2OH)

What is Benzyl Alcohol?

Benzyl alcohol is an organic compound with the chemical formula C6H5CH2OH. The IUPAC name of this compound is phenyl methanol. At room temperature, benzyl alcohol exists as a colorless liquid that has a mildly aromatic smell. When this aromatic alcohol is deprotonated, the resulting anion is called a benzylate.

This compound is not very soluble in water. However, it forms miscible mixtures with diethyl ether and other alcohols. Many plants are known to naturally produce C6H5CH2OH. The essential oils extracted from jasmine, ylang-ylang, and hyacinth contain some amount of benzyl alcohol.

Structure

This compound consists of a hydroxyl group attached to a methyl group, which is in turn attached to an aromatic ring. The structure of a C6H5CH2OH molecule is illustrated below.

Benzyl Alcohol

The pi electrons in the benzene ring are delocalized due to resonance. Essentially, the structure of a benzyl alcohol molecule is that of a toluene molecule in which one of the hydrogen atoms has been replaced by a hydroxyl group.

Preparation

The use of sodium hydroxide in the hydrolysis of benzyl chloride yields benzyl alcohol and sodium chloride as the products. The chemical equation for this reaction is given by:

NaOH + C6H5CH2Cl → NaCl + C6H5CH2OH

An alternate method of preparing this compound involves the Grignard reaction between formaldehyde (H-CHO) and phenylmagnesium bromide (Ph-Mg-Br).

Properties of C6H5CH2OH

Chemical Data

Benzyl Alcohol C6H5CH2OH
Molar Mass 108.14 grams per mole
Density 1.044 grams per cubic centimeter
Melting Point 257.9 K (-15.2oC)
Boiling Point 478.4 K (205.3oC)

Physical Properties

  • Under standard conditions, benzyl alcohol is a colorless, slightly aromatic liquid.
  • Its solubility in water corresponds to 3.5g/100mL at 20oC and 4.29g/100mL at 25o
  • This compound is soluble in several organic solvents such as benzene, methanol, acetone, and ether.

Chemical Properties

  • The reaction between carboxylic acids and benzyl alcohol leads to the formation of esters.
  • This compound undergoes a Ritter reaction with acrylonitrile to yield N-benzyl acrylamide.
  • When deprotonated, C6H5CH2OH yields a benzylate anion.

What are the Uses of Benzyl Alcohol?

This compound is widely used as a solvent for epoxy resin coatings, inks, and paints. Some other applications of benzyl alcohol are listed below.

  • C6H5CH2OH is a precursor to several esters.
  • A solution of benzyl alcohol with a concentration of 10% can be used as a local anesthetic and also as an antimicrobial agent.
  • This compound is a component of the fluid mixtures used in electronic cigarettes (it enhances the flavor).
  • Benzyl alcohol can serve as a dielectric solvent for the reconfiguration of some nanowires via dielectrophoresis.
  • 5% solutions of this compound can be used to treat head lice.
  • It is used in the manufacture of soaps, shampoos, and skin lotions because of its antifungal and antibacterial properties.

To learn more about benzyl alcohol and other important aromatic compounds (such as acetic acid), register with BYJU’S and download the mobile application on your smartphone.

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