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Benzyl alcohol



Benzyl alcohol
IUPAC name Benzyl alcohol
Other names Phenylmethanol
Phenylcarbinol
Identifiers
CAS number 100-51-6
SMILES OCc1ccccc1
Properties
Molecular formula C7H8O
Molar mass 108.14 g/mol
Density 1.044 g/cm3
Melting point

-15 °C

Boiling point

205 °C

Hazards
MSDS ScienceLab.com
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Benzyl alcohol is an organic compound with the formula C6H5CH2OH. The benzyl group is commonly abbreviated "Bn", thus BnOH, for benzyl alcohol. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is a natural constituent of a variety of essential oils including jasmine, hyacinth, and ylang-ylang.[1] Benzyl alcohol is also a useful solvent due to its polarity, low toxicity, and low vapor pressure.

Benzyl alcohol is partially soluble in water (4 g/100 mL) and completely miscible in alcohols and ether. It is prepared by the hydrolysis of benzyl chloride using sodium hydroxide:

C6H5CH2Cl + NaOH → C6H5CH2OH + NaCl

It can also be prepared via a Grignard reaction by reacting phenylmagnesium bromide (C6H5MgBr) with formaldehyde, followed by acidification. Like most alcohols, it reacts with carboxylic acids to form esters.

Additional recommended knowledge

Contents

Applications

Benzyl alcohol is used as a general solvent for inks, paints, lacquers, and epoxy resin coatings.[2] It is also a precursor to a variety of esters, used in the soap, perfume, and flavor industries, as well as for pharmaceuticals. It exhibits bacteriostatic and antipruritic properties. It is also used as a photographic developer.

Illustrative organic synthetic uses

In organic synthesis, benzyl esters are popular protecting groups because they can be removed by mild hydrogenolysis.[3]

BnOH reacts with acrylonitrile to give N-benzylacrylamide. This is an example of a Ritter reaction:[4]

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

Nanotechnological uses

Benzyl alcohol has been used as a dielectric solvent for the dielectrophoretic reconfiguration of nanowires.[5]

Health & safety

Benzyl alcohol is used as a bacteriostatic preservative in parenteral (IV) medications. Benzyl alcohol is also known for its toxic effects including respiratory failure, vasodilation, hypotension, convulsions, and paralysis. Sixteen Neonatal deaths have been associated with the use of benzyl alcohol as a preservative in saline flush solutions.[6] Preservative free solutions are now being used for the infant population.[citation needed]

Benzyl alcohol should be avoided by people with perfume allergy.[citation needed]

References

  1. ^ Merck Index, 11th Edition, 1138.
  2. ^ Benzyl alcohol at chemicalland21.com
  3. ^ Furuta, K.; Gao, Q.-Z.; Yamamoto, H. (1998). "Chiral (Acyloxy)borane Complex-Catalyzed Asymmetric Diels-Alder Reaction: (1R)-1,3,4-Trimethyl-3-Cyclohexene-1-Carboxaldehyde". Org. Synth.; Coll. Vol. 9: 722. 
  4. ^ Parris, C. L. (1973). "N-benzylacrylamide". Org. Synth.; Coll. Vol. 5: 73. 
  5. ^ Alexander Wissner-Gross (19 Oct 2006). "Nanowires get reconfigured". Nanotechweb.org.
  6. ^ (11 Jun 1982) "Neonatal Deaths Associated With Use Of Benzyl Alcohol — United States". Morbidity and Mortality Weekly Report 31 (22): 290-1.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Benzyl_alcohol". A list of authors is available in Wikipedia.
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