Benzoin
1969188
216892756
2008-06-03T18:19:58Z
198.102.159.141
{{Chembox new
| ImageFile = Benzoin.png
| ImageFile1 = Benzoin-3D-balls.png
| IUPACName =
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 119-53-9
| PubChem =
| SMILES = O=C(c2ccccc2)C(O)c1ccccc1
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>14</sub>H<sub>12</sub>O<sub>2</sub>
| MolarMass = 212.25 g/mol
| Appearance =
| Density = 1.31 g/cm<sup>3</sup>
| MeltingPt = 137 °C
| BoilingPt = 344 °C
| Solubility = Slightly Soluble
| Solvent = [[ethanol]]
| SolubleOther = Slightly Soluble
| Solvent = [[alcohol]]
| SolubleOther = Soluble
| Solvent = [[ether]]
| SolubleOther = Slightly Soluble
| Solvent = [[Chlorine]]
| SolubleOther = Soluble
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| Autoignition =
}}
}}
:''"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:
* [[photocatalyst]] in [[photopolymerization]] and a [[photoinitiator]]
* raw material for [[benzil]] by [[organic oxidation]] with [[nitric acid]] or [[oxone]]. In one study,<ref>{{cite journal|title=A very simple and chemoselective air oxidation of benzoins to benzils using alumina| author=Konstantinos Skobridis, Vassiliki Theodorou, Edwin Weber| journal=[[Arkivoc]] |volume=06-1798JP|pages=102–106| date=2006| url=http://www.arkat-usa.org/ark/journal/2006/I10_General/1798/06-1798JP%20as%20published%20mainmanuscript.asp}}</ref> this reaction is carried out with atmospheric oxygen and basic [[alumina]] in [[dichloromethane]].
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]].<ref>{{cite journal
| title = Untersuchungen über das Radikal der Benzoesäure
| author = Wöhler, Liebig
| journal = Annalen der Pharmacie
| volume = 3
| issue = 3
| pages = 249–282
| year = 1832
| url =
| doi = 10.1002/jlac.18320030302 }}</ref> The catalytic synthesis by the [[benzoin condensation]] was improved by the research of [[Nikolay Zinin]] during his time with Liebig. <ref>{{cite journal
| title = Beiträge zur Kenntniss einiger Verbindungen aus der Benzoylreihe
| author = N. Zinin
| journal = Annalen der Pharmacie
| volume = 31
| issue = 3
| pages = 329–332
| year = 1839
| url =
| doi = 10.1002/jlac.18390310312 }}</ref><ref>{{cite journal
| title = Ueber einige Zersetzungsprodukte des Bittermandelöls
| author = N. Zinin
| journal = Annalen der Pharmacie
| volume = 34
| issue = 2
| pages = 186–192
| year = 1840
| url =
| doi = 10.1002/jlac.18400340205 }}</ref>
==References==
{{reflist}}
*[http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0094 Synthesis]
[[Category:alcohols]]
[[Category:ketones]]
[[Category:Aromatic compounds]]
[[Category:Arabic words and phrases]]
[[ar:بنزوين]]
[[de:Benzoe]]
[[es:Benzoína]]
[[fr:Benjoin]]
[[ja:ベンゾイン]]
[[pl:Benzoina]]
[[vi:Benzoin]]
[[zh:安息香]]