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Phenethyl alcohol

Phenethyl alcohol
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
2-Phenylethan-1-ol
Other names
2-Phenylethanol
Phenethyl alcohol
Benzyl carbinol
β-Hydroxyethylbenzene
Benzenethanol
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.000.415
PubChem CID
UNII
Properties
C8H10O
Molar mass 122.16 g/mol
Odor Soft, like roses
Density 1.017 g/cm3
Melting point −27 °C (−17 °F; 246 K)
Boiling point 219 to 221 °C (426 to 430 °F; 492 to 494 K)
Hazards
Safety data sheet JT Baker MSDS
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Phenethyl alcohol, or 2-phenylethanol, is the organic compound that consists of a phenethyl group (C6H5CH2CH2) group attached to OH. It is a colourless liquid that is slightly soluble in water (2 ml/100 ml H2O), but miscible with most organic solvents. It occurs widely in nature, being found in a variety of essential oils. It has a pleasant floral odor.

Phenethyl alcohol is prepared commercially via two routes. Most common is the Friedel-Crafts reaction between benzene and ethylene oxide in the presence of aluminium trichloride.

The reaction affords the aluminium alkoxide that is subsequently hydrolyzed to the desired product. The main side product is diphenylethane, which can be avoided by use of excess benzene. Hydrogenation of styrene oxide also affords phenethyl alcohol.

Phenethyl alcohol can also be prepared by the reaction between phenylmagnesium bromide and ethylene oxide:

Phenethyl alcohol can also be produced by biotransformation from L-phenylalanine using immobilized yeast Saccharomyces cerevisiae.

Phenethyl alcohol is found in extract of rose, carnation, hyacinth, Aleppo pine, orange blossom, ylang-ylang, geranium, neroli, and champaca. It is also an autoantibiotic produced by the fungus Candida albicans


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