Benzyl alcohol
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| Benzyl alcohol | |
|---|---|
| Image:Benzyl-alcohol-2D-skeletal.png | |
| Image:Benzyl-alcohol-3D-vdW.png | |
| IUPAC name | Benzyl alcohol |
| Other names | Phenylmethanol Phenylcarbinol |
| Identifiers | |
| CAS number | |
| 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:
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
Applications
Benzyl alcohol is used as a general solvent for inks, paints, lacquers, and epoxy resin coatings.[1] 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.[1]
BnOH reacts with acrylonitrile to give N-benzylacrylamide. This is an example of a Ritter reaction:[1]
- C6H5CH2OH + NCCHCH2 → C6H5CH2N(H)C(O)CHCH2
Nanotechnological uses
Benzyl alcohol has been used as a dielectric solvent for the dielectrophoretic reconfiguration of nanowires.[1]
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.[1] 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
de:Benzylalkohol fr:Alcool benzylique nl:Benzylalcohol ja:ベンジルアルコールfi:Bentsyylialkoholi
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
