Phenethyl alcohol

Source: Wikipedia, the free encyclopedia.
Phenethyl alcohol[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
2-Phenylethanol
Other names
2-Phenylethanol
Phenethyl alcohol
Benzyl carbinol
β-Hydroxyethylbenzene
Benzeneethanol
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.000.415 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2 checkY
    Key: WRMNZCZEMHIOCP-UHFFFAOYSA-N checkY
  • 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
  • c1ccc(cc1)CCO
Properties
C8H10O
Molar mass 122.167 g·mol−1
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)
log P 1.36 [2]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Safety data sheet (SDS) JT Baker MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Phenethyl alcohol, or 2-phenylethanol, is an

hydroxyl group
(−OH).

Synthesis

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
.

C6H6 + CH2CH2O + AlCl3 → C6H5CH2CH2OAlCl2 + HCl

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.[3]

Laboratory methods

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

C6H5MgBr + CH2CH2O → C6H5CH2CH2OMgBr
C6H5CH2CH2OMgBr + H+ → C6H5CH2CH2OH + MgBr+

Phenethyl alcohol can also be produced by

THF. [5]

Occurrence and uses

Phenethyl alcohol is found in extract of

autoantibiotic produced by the fungus Candida albicans.[6]

Fusel alcohols like phenethyl alcohol are grain fermentation byproducts, and therefore trace amounts of phenethyl alcohol are present in many alcoholic beverages.

It is therefore a common ingredient in flavors and perfumery, particularly when the odor of rose is desired.[3] It is used as an additive in cigarettes. It is also used as a preservative in soaps due to its stability in basic conditions. It is of interest due to its antimicrobial properties.

See also

References

  1. ^ Merck Index (11th ed.). p. 7185.
  2. ^ "Phenylethyl alcohol_msds".
  3. ^
    ISBN 978-3-527-30673-2
    .
  4. PMID 19200319
    .
  5. doi:10.1021/jo00020a052
    .
  6. S2CID 12430791
    .
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