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Benzoin



Benzoin
Identifiers
CAS number 119-53-9
SMILES O=C(c2ccccc2)C(O)c1ccccc1
Properties
Molecular formula C14H12O2
Molar mass 212.25 g/mol
Density 1.31 g/cm3
Melting point

137 °C

Boiling point

344 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
"Benzoin" is also used to describe benzoin resin, which does not contain the benzoin described on this page.

Benzoin or 2-Hydroxy-2-phenylacetophenone or 2-Hydroxy-1,2-Diphenylethanone or desyl alcohol or bitter almond oil camphor is an organic compound consisting of an ethylene bridge flanked by phenyl groups and with a hydroxyl and a ketone functional group. It comes as off-white crystals, with a light camphor odor. Benzoin is synthesized from benzaldehyde in the benzoin condensation.

Its main uses are:

Benzoin is not a constituent of benzoin resin obtained from the benzoin tree (Styrax) or tincture of benzoin. The main component in these natural products is benzoic acid.

History

Benzoin was first synthesized in 1832 by Justus von Liebig and Friedrich Woehler during the research on bitter almond oil, which was benzaldehyde with traces of hydrocyanic acid.[2] The catalytic synthesis by the benzoin condensation was improved by the research of Nikolay Zinin during his time with Liebig. [3][4]

References

  1. ^ Konstantinos Skobridis, Vassiliki Theodorou, Edwin Weber (2006). "A very simple and chemoselective air oxidation of benzoins to benzils using alumina". Arkivoc 06-1798JP: 102-106.
  2. ^ Wöhler, Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie 3 (3): 249 - 282. doi:10.1002/jlac.18320030302.
  3. ^ N. Zinin (1839). "Beiträge zur Kenntniss einiger Verbindungen aus der Benzoylreihe". Annalen der Pharmacie 31 (3): 329 - 332. doi:10.1002/jlac.18390310312.
  4. ^ N. Zinin (1840). "Ueber einige Zersetzungsprodukte des Bittermandelöls". Annalen der Pharmacie 34 (2): 186 - 192. doi:10.1002/jlac.18400340205.
  • Synthesis
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Benzoin". A list of authors is available in Wikipedia.
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