|IUPAC name||Benzyl alcohol|
3D model (JSmol)
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|Molar mass||108.14 g/mol|
|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. Benzyl alcohol is also a useful solvent due to its polarity, low toxicity, and low vapor pressure.
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
Benzyl alcohol is used as a general solvent for inks, paints, lacquers, and epoxy resin coatings. 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
- C6H5CH2OH + NCCHCH2 → C6H5CH2N(H)C(O)CHCH2
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. Preservative free solutions are now being used for the infant population.
Benzyl alcohol should be avoided by people with perfume allergy.
- Merck Index, 11th Edition, 1138.
- Benzyl alcohol at chemicalland21.com
- 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.
- Parris, C. L. (1973). "N-benzylacrylamide". Org. Synth.; Coll. Vol. 5: 73.
- Alexander Wissner-Gross (19 Oct 2006). "Nanowires get reconfigured". Nanotechweb.org.
- "Neonatal Deaths Associated With Use Of Benzyl Alcohol — United States". Morbidity and Mortality Weekly Report. 31 (22): 290–1. 11 Jun 1982.