Phenethyl alcohol

Phenethyl alcohol[1]
Identifiers
CAS number 60-12-8 Y
PubChem 6054
ChemSpider 5830 Y
UNII ML9LGA7468 Y
DrugBank DB02192
ChEBI CHEBI:49000 Y
ChEMBL CHEMBL448500 Y
Jmol-3D images Image 1
Properties
Molecular formula C8H10O
Molar mass 122.16 g/mol
Density 1.017 g/cm3
Melting point

-27 °C, 246 K, -17 °F

Boiling point

219–221 °C

Hazards
MSDS JT Baker MSDS
NFPA 704
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Phenethyl alcohol, or 2-phenylethanol, is the organic compound with the formula C6H5CH2CH2OH. This colourless liquid occurs widely in nature, being found in a variety of essential oils, including rose, carnation, hyacinth, Aleppo pine, orange blossom, ylang-ylang, geranium, neroli, and champaca. It is slightly soluble in water (2 mL/100 mL H2O), but miscible with ethanol and ether.

Phenethyl alcohol is an alcohol with a pleasant floral odor. It is therefore a common ingredient in flavors and perfumery, particularly when the smell of rose is desired. It is used as an additive in cigarettes. It is also used as a preservative in soaps due to its stability in basic conditions. In biology it is of interest due to its antimicrobial properties.

Synthesis

Phenethyl alcohol can be prepared by a variety of procedures, such as by a Grignard reaction between phenylmagnesium bromide and ethylene oxide:

C6H5MgBr + CH2CH2O → C6H5CH2CH2OMgBr
C6H5CH2CH2OMgBr + H+ → C6H5CH2CH2OH

However, the Friedel-Crafts reaction between benzene and ethylene oxide may also be employed:

C6H6 + CH2CH2O (+ AlCl3) → C6H5CH2CH2OH (+AlCl3)

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

References

  1. ^ Merck Index, 11th Edition, 7185.

See also