Phenethyl alcohol

Phenethyl alcohol
IUPAC name 2-Phenylethanol
Other names Phenethyl alcohol Benzyl carbinol β-Hydroxyethylbenzene Benzenethanol
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
SMILES c1ccc(cc1)CCO
InChI InChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2 Y Key: WRMNZCZEMHIOCP-UHFFFAOYSA-N Y InChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2 InChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2 Key: WRMNZCZEMHIOCP-UHFFFAOYSA-N
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	1 1 0
Y (verify) (what is: Y/N?) 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.^{[citation needed]}

See also

• Phenethylamine