Benzyl alcohol
From Wikipedia, the free encyclopedia
| Benzyl alcohol | |
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| Chemical name | Benzyl alcohol |
| Other names | Phenylmethanol Phenylcarbinol |
| Chemical formula | C7H8O |
| Molecular mass | 108.14 g/mol |
| CAS number | [100-51-6] |
| Density | 1.044 g/cm3 |
| Melting point | -15 °C |
| Boiling point | 205 °C |
| SMILES | OCc1ccccc1 |
| 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, reacts with carboxylic acids to form esters.
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[edit] 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.
[edit] 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
[edit] References
- ^ Merck Index, 11th Edition, 1138.
- ^ Benzyl alcohol at chemicalland21.com
- ^ Furuta, K.; Gao, Q.-Z.; Yamamoto, H. "Chiral (Acyloxy)borane Complex-Catalyzed Asymmetric Diels-Alder Reaction: (1R)-1,3,4-Trimethyl-3-Cyclohexene-1-Carboxaldehyde" Organic Syntheses, Collected Volume 9, p.722 (1998)
- ^ Parris, C. L. "N-benzylacrylamide" Organic Syntheses, Collected Volume 5, p.73 (1973). (Article)
